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Showing metabocard for (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA (HMDB0301648)

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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-22 01:47:25 UTC
Update Date2021-10-01 16:55:10 UTC
HMDB IDHMDB0301648
Secondary Accession NumbersNone
Metabolite Identification
Common Name(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA
Description(5z)-7-{2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (5Z)-7-{2-[(1E)-3_3-difluoro-4-phenoxybut-1-en-1-yl]-3_5-dihydroxycyclopentyl}hept-5-enoic acid thioester of coenzyme A. (5z)-7-{2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-coa is an acyl-CoA with 22 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. (5z)-7-{2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-coa is therefore classified as a very long chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. (5z)-7-{2-[(1e)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-coa, being a very long chain acyl-CoA is a substrate for very long chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA into (5Z)-7-{2-[(1E)-3_3-difluoro-4-phenoxybut-1-en-1-yl]-3_5-dihydroxycyclopentyl}hept-5-enoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (5Z)-7-{2-[(1E)-3_3-difluoro-4-phenoxybut-1-en-1-yl]-3_5-dihydroxycyclopentyl}hept-5-enoylcarnitine is converted back to (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA occurs in four steps. First, since (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)


  Mrv1652304102106012D          

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M  END
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3D MOL for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)

HMDB0301648
     RDKit          3D
(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl...
138142  0  0  0  0  0  0  0  0999 V2000
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M  END
Download

3D SDF for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)


  Mrv1652304102106012D          

 76 80  0  0  0  0            999 V2000
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   20.5393    1.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.4039    2.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0301648

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC=CCC1C(O)CC(O)C1C=CC(F)(F)COC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C43H62F2N7O20P3S/c1-42(2,22-69-75(65,66)72-74(63,64)68-21-31-36(71-73(60,61)62)35(57)41(70-31)52-25-51-34-38(46)49-24-50-39(34)52)37(58)40(59)48-17-15-32(55)47-18-19-76-33(56)13-9-4-3-8-12-27-28(30(54)20-29(27)53)14-16-43(44,45)23-67-26-10-6-5-7-11-26/h3,5-8,10-11,14,16,24-25,27-31,35-37,41,53-54,57-58H,4,9,12-13,15,17-23H2,1-2H3,(H,47,55)(H,48,59)(H,63,64)(H,65,66)(H2,46,49,50)(H2,60,61,62)

> <INCHI_KEY>
GSLXROZZPAZVPZ-UHFFFAOYSA-N

> <FORMULA>
C43H62F2N7O20P3S

> <MOLECULAR_WEIGHT>
1159.98

> <EXACT_MASS>
1159.295125918

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
109.26674846423592

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({7-[2-(3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl]hept-5-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
-2.2852280628146273

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776186

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.820978781339821

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
413.32000000000005

> <JCHEM_REFRACTIVITY>
266.2171

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({7-[2-(3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl]hept-5-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)

HMDB0301648
     RDKit          3D
(5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl...
138142  0  0  0  0  0  0  0  0999 V2000
   -4.6590   -0.1926    2.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1091    0.3022   -0.8811 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5134   -3.0259    1.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172   -4.7204    1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058   -3.0007    1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6108   -3.1570   -1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5637   -2.2423   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -1.2292   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803   -0.3168   -0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -0.3575   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9485    1.2141   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1198    2.1735   -0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1836    1.4330    0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2137    1.0459   -0.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4350    0.3801   -1.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5669   -1.5793   -0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2412   -2.3903    1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5786    0.4275    0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5316   -0.7269    2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8129   -1.3250   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9836   -3.0680    1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3999   -3.2574   -0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5548   -3.1833    3.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8623   -3.2339    2.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3159   -1.0649    2.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6608    0.3287    3.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9055    0.4625    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4663   -2.0724    0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6205    0.9367   -0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3347    1.3525   -2.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8069    0.3661   -2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2065    2.4436    1.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6258    4.4366    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.4178    5.5669    0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.8089    4.7303   -2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3813    2.7244   -2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 17 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
  2 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 43 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  2  0
 49 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
 54 55  2  3
 55 56  1  0
 56 57  1  0
 57 58  1  0
 58 59  1  0
 58 60  1  0
 60 61  1  0
 61 62  1  0
 61 63  1  0
 63 64  1  0
 64 65  2  3
 65 66  1  0
 66 67  1  0
 66 68  1  0
 66 69  1  0
 69 70  1  0
 70 71  1  0
 71 72  2  0
 72 73  1  0
 73 74  2  0
 74 75  1  0
 75 76  2  0
 30 15  1  0
 63 57  1  0
 76 71  1  0
 27 18  1  0
 27 21  1  0
  1 77  1  0
  1 78  1  0
  1 79  1  0
  3 80  1  0
  3 81  1  0
  3 82  1  0
  4 83  1  0
  4 84  1  0
  8 85  1  0
 12 86  1  0
 14 87  1  0
 14 88  1  0
 15 89  1  0
 17 90  1  0
 19 91  1  0
 23 92  1  0
 23 93  1  0
 25 94  1  0
 28 95  1  0
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 30 97  1  0
 34 98  1  0
 35 99  1  0
 36100  1  0
 37101  1  0
 40102  1  0
 41103  1  0
 41104  1  0
 42105  1  0
 42106  1  0
 45107  1  0
 46108  1  0
 46109  1  0
 47110  1  0
 47111  1  0
 51112  1  0
 51113  1  0
 52114  1  0
 52115  1  0
 53116  1  0
 53117  1  0
 54118  1  0
 55119  1  0
 56120  1  0
 56121  1  0
 57122  1  0
 58123  1  0
 59124  1  0
 60125  1  0
 60126  1  0
 61127  1  0
 62128  1  0
 63129  1  0
 64130  1  0
 65131  1  0
 69132  1  0
 69133  1  0
 72134  1  0
 73135  1  0
 74136  1  0
 75137  1  0
 76138  1  0
M  END
Download

PDB for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)

HEADER    PROTEIN                                 10-APR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-APR-21         0                                  
HETATM    1  O   UNK     0      33.049   3.012   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      33.049   1.472   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      31.715   0.702   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      30.381   1.472   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.047   0.702   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      27.714   1.472   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      26.380   0.702   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      26.380  -0.838   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      25.046   1.472   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.713   0.702   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      22.379   1.472   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      21.045   0.702   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      21.045  -0.838   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      19.712   1.472   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      19.712   3.012   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.378   0.702   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.148  -0.632   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.608   2.036   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.044  -0.068   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.711   0.702   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      14.377  -0.068   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      15.147  -1.402   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.607   1.266   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.043  -0.838   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      11.710  -0.068   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      10.940  -1.402   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      12.480   1.266   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.376   0.702   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.042  -0.068   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.709   0.702   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.302   0.076   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.271   1.220   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       3.740   1.059   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.970  -0.274   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       1.463   0.046   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       1.302   1.577   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.057   2.483   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       0.217   4.014   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       1.624   4.640   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0       2.870   3.735   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0       2.709   2.204   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      -1.350   1.856   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0       6.041   2.554   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       5.415   3.961   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       7.548   2.234   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       8.692   3.264   0.000  0.00  0.00           O+0
HETATM   47  P   UNK     0      10.157   2.788   0.000  0.00  0.00           P+0
HETATM   48  O   UNK     0       9.681   1.324   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      10.633   4.253   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      11.621   2.312   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      34.382   0.702   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      35.716   1.472   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      37.050   0.702   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      38.383   1.472   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      39.717   0.702   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      41.051   1.472   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      41.051   3.012   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      39.805   3.917   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      38.340   3.441   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      40.281   5.382   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      41.821   5.382   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      42.726   6.628   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      42.296   3.917   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      43.761   3.441   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      44.081   1.935   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      45.546   1.459   0.000  0.00  0.00           C+0
HETATM   67  F   UNK     0      45.070  -0.005   0.000  0.00  0.00           F+0
HETATM   68  F   UNK     0      46.022   2.924   0.000  0.00  0.00           F+0
HETATM   69  C   UNK     0      47.011   0.983   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      48.155   2.014   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      49.620   1.538   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      50.764   2.568   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      52.229   2.092   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      52.549   0.586   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      51.404  -0.444   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      49.940   0.032   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   51                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   45                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   43                                                  
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36   33                                                  
CONECT   42   37                                                            
CONECT   43   32   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   30   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47                                                            
CONECT   51    2   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   63                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61                                                       
CONECT   61   60   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   57   64                                                  
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   68   69                                             
CONECT   67   66                                                            
CONECT   68   66                                                            
CONECT   69   66   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72   76                                                  
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76                                                       
CONECT   76   75   71                                                       
MASTER        0    0    0    0    0    0    0    0   76    0  160    0
END
Download

3D PDB for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)

COMPND    HMDB0301648
HETATM    1  C1  UNL     1      -4.659  -0.193   2.496  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.985  -0.518   1.073  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.739  -1.852   1.030  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.787   0.573   0.443  1.00  0.00           C  
HETATM    5  O1  UNL     1      -6.109   0.302  -0.881  1.00  0.00           O  
HETATM    6  P1  UNL     1      -7.019   1.556  -1.552  1.00  0.00           P  
HETATM    7  O2  UNL     1      -6.190   2.110  -2.713  1.00  0.00           O  
HETATM    8  O3  UNL     1      -8.460   0.955  -2.201  1.00  0.00           O  
HETATM    9  O4  UNL     1      -7.274   2.815  -0.487  1.00  0.00           O  
HETATM   10  P2  UNL     1      -8.849   2.965   0.054  1.00  0.00           P  
HETATM   11  O5  UNL     1      -9.256   4.440   0.111  1.00  0.00           O  
HETATM   12  O6  UNL     1      -9.009   2.393   1.659  1.00  0.00           O  
HETATM   13  O7  UNL     1      -9.914   2.169  -0.972  1.00  0.00           O  
HETATM   14  C5  UNL     1     -10.619   1.240  -0.213  1.00  0.00           C  
HETATM   15  C6  UNL     1     -11.604   0.463  -1.024  1.00  0.00           C  
HETATM   16  O8  UNL     1     -12.523   1.337  -1.587  1.00  0.00           O  
HETATM   17  C7  UNL     1     -13.382   1.704  -0.588  1.00  0.00           C  
HETATM   18  N1  UNL     1     -14.660   2.087  -1.211  1.00  0.00           N  
HETATM   19  C8  UNL     1     -14.947   2.109  -2.528  1.00  0.00           C  
HETATM   20  N2  UNL     1     -16.222   2.511  -2.721  1.00  0.00           N  
HETATM   21  C9  UNL     1     -16.771   2.752  -1.535  1.00  0.00           C  
HETATM   22  C10 UNL     1     -18.031   3.179  -1.177  1.00  0.00           C  
HETATM   23  N3  UNL     1     -19.070   3.464  -2.101  1.00  0.00           N  
HETATM   24  N4  UNL     1     -18.287   3.332   0.133  1.00  0.00           N  
HETATM   25  C11 UNL     1     -17.332   3.074   1.064  1.00  0.00           C  
HETATM   26  N5  UNL     1     -16.106   2.658   0.697  1.00  0.00           N  
HETATM   27  C12 UNL     1     -15.789   2.486  -0.595  1.00  0.00           C  
HETATM   28  C13 UNL     1     -13.557   0.462   0.250  1.00  0.00           C  
HETATM   29  O9  UNL     1     -14.803  -0.076  -0.040  1.00  0.00           O  
HETATM   30  C14 UNL     1     -12.445  -0.463  -0.169  1.00  0.00           C  
HETATM   31  O10 UNL     1     -11.723  -0.966   0.911  1.00  0.00           O  
HETATM   32  P3  UNL     1     -11.761  -2.642   0.943  1.00  0.00           P  
HETATM   33  O11 UNL     1     -12.731  -3.206  -0.070  1.00  0.00           O  
HETATM   34  O12 UNL     1     -12.200  -3.110   2.518  1.00  0.00           O  
HETATM   35  O13 UNL     1     -10.233  -3.280   0.563  1.00  0.00           O  
HETATM   36  C15 UNL     1      -3.737  -0.742   0.237  1.00  0.00           C  
HETATM   37  O14 UNL     1      -4.164  -1.031  -1.070  1.00  0.00           O  
HETATM   38  C16 UNL     1      -2.941  -1.886   0.766  1.00  0.00           C  
HETATM   39  O15 UNL     1      -2.513  -1.819   1.934  1.00  0.00           O  
HETATM   40  N6  UNL     1      -2.666  -3.034  -0.017  1.00  0.00           N  
HETATM   41  C17 UNL     1      -1.905  -4.142   0.502  1.00  0.00           C  
HETATM   42  C18 UNL     1      -0.521  -3.776   0.936  1.00  0.00           C  
HETATM   43  C19 UNL     1       0.322  -3.232  -0.155  1.00  0.00           C  
HETATM   44  O16 UNL     1      -0.191  -3.116  -1.285  1.00  0.00           O  
HETATM   45  N7  UNL     1       1.652  -2.879   0.152  1.00  0.00           N  
HETATM   46  C20 UNL     1       2.532  -2.350  -0.864  1.00  0.00           C  
HETATM   47  C21 UNL     1       2.040  -1.080  -1.480  1.00  0.00           C  
HETATM   48  S1  UNL     1       3.116  -0.377  -2.726  1.00  0.00           S  
HETATM   49  C22 UNL     1       4.577   0.351  -2.062  1.00  0.00           C  
HETATM   50  O17 UNL     1       5.436   0.707  -2.853  1.00  0.00           O  
HETATM   51  C23 UNL     1       4.796   0.544  -0.628  1.00  0.00           C  
HETATM   52  C24 UNL     1       6.114   1.207  -0.281  1.00  0.00           C  
HETATM   53  C25 UNL     1       7.325   0.448  -0.700  1.00  0.00           C  
HETATM   54  C26 UNL     1       7.407  -0.898  -0.094  1.00  0.00           C  
HETATM   55  C27 UNL     1       8.351  -1.358   0.687  1.00  0.00           C  
HETATM   56  C28 UNL     1       9.556  -0.646   1.149  1.00  0.00           C  
HETATM   57  C29 UNL     1      10.819  -1.339   0.719  1.00  0.00           C  
HETATM   58  C30 UNL     1      10.913  -2.720   1.269  1.00  0.00           C  
HETATM   59  O18 UNL     1      11.359  -3.644   0.327  1.00  0.00           O  
HETATM   60  C31 UNL     1      11.948  -2.687   2.393  1.00  0.00           C  
HETATM   61  C32 UNL     1      12.246  -1.235   2.616  1.00  0.00           C  
HETATM   62  O19 UNL     1      11.460  -0.640   3.589  1.00  0.00           O  
HETATM   63  C33 UNL     1      12.042  -0.638   1.253  1.00  0.00           C  
HETATM   64  C34 UNL     1      13.217  -1.008   0.419  1.00  0.00           C  
HETATM   65  C35 UNL     1      13.925  -0.093  -0.239  1.00  0.00           C  
HETATM   66  C36 UNL     1      15.079  -0.518  -1.049  1.00  0.00           C  
HETATM   67  F1  UNL     1      15.893  -1.328  -0.267  1.00  0.00           F  
HETATM   68  F2  UNL     1      14.751  -1.176  -2.200  1.00  0.00           F  
HETATM   69  C37 UNL     1      15.933   0.687  -1.447  1.00  0.00           C  
HETATM   70  O20 UNL     1      16.387   1.310  -0.279  1.00  0.00           O  
HETATM   71  C38 UNL     1      17.181   2.425  -0.242  1.00  0.00           C  
HETATM   72  C39 UNL     1      17.549   2.931   1.009  1.00  0.00           C  
HETATM   73  C40 UNL     1      18.344   4.049   1.103  1.00  0.00           C  
HETATM   74  C41 UNL     1      18.789   4.684  -0.014  1.00  0.00           C  
HETATM   75  C42 UNL     1      18.443   4.208  -1.260  1.00  0.00           C  
HETATM   76  C43 UNL     1      17.648   3.091  -1.349  1.00  0.00           C  
HETATM   77  H1  UNL     1      -4.425  -1.118   3.073  1.00  0.00           H  
HETATM   78  H2  UNL     1      -3.892   0.587   2.569  1.00  0.00           H  
HETATM   79  H3  UNL     1      -5.588   0.236   2.955  1.00  0.00           H  
HETATM   80  H4  UNL     1      -5.128  -2.603   1.564  1.00  0.00           H  
HETATM   81  H5  UNL     1      -5.780  -2.124  -0.056  1.00  0.00           H  
HETATM   82  H6  UNL     1      -6.723  -1.784   1.491  1.00  0.00           H  
HETATM   83  H7  UNL     1      -6.765   0.629   0.995  1.00  0.00           H  
HETATM   84  H8  UNL     1      -5.329   1.559   0.536  1.00  0.00           H  
HETATM   85  H9  UNL     1      -8.654   1.441  -3.020  1.00  0.00           H  
HETATM   86  H10 UNL     1      -8.295   2.734   2.226  1.00  0.00           H  
HETATM   87  H11 UNL     1      -9.855   0.599   0.279  1.00  0.00           H  
HETATM   88  H12 UNL     1     -11.182   1.812   0.564  1.00  0.00           H  
HETATM   89  H13 UNL     1     -11.120  -0.180  -1.788  1.00  0.00           H  
HETATM   90  H14 UNL     1     -13.029   2.545   0.034  1.00  0.00           H  
HETATM   91  H15 UNL     1     -14.289   1.852  -3.349  1.00  0.00           H  
HETATM   92  H16 UNL     1     -19.734   4.243  -1.920  1.00  0.00           H  
HETATM   93  H17 UNL     1     -19.206   2.917  -2.978  1.00  0.00           H  
HETATM   94  H18 UNL     1     -17.577   3.210   2.108  1.00  0.00           H  
HETATM   95  H19 UNL     1     -13.464   0.752   1.320  1.00  0.00           H  
HETATM   96  H20 UNL     1     -14.865  -0.158  -1.024  1.00  0.00           H  
HETATM   97  H21 UNL     1     -12.867  -1.292  -0.744  1.00  0.00           H  
HETATM   98  H22 UNL     1     -13.181  -3.020   2.643  1.00  0.00           H  
HETATM   99  H23 UNL     1     -10.240  -4.254   0.733  1.00  0.00           H  
HETATM  100  H24 UNL     1      -3.100   0.148   0.161  1.00  0.00           H  
HETATM  101  H25 UNL     1      -3.999  -0.299  -1.697  1.00  0.00           H  
HETATM  102  H26 UNL     1      -3.035  -3.061  -0.998  1.00  0.00           H  
HETATM  103  H27 UNL     1      -2.498  -4.554   1.367  1.00  0.00           H  
HETATM  104  H28 UNL     1      -1.899  -4.968  -0.255  1.00  0.00           H  
HETATM  105  H29 UNL     1      -0.513  -3.026   1.746  1.00  0.00           H  
HETATM  106  H30 UNL     1      -0.017  -4.720   1.267  1.00  0.00           H  
HETATM  107  H31 UNL     1       2.006  -3.001   1.120  1.00  0.00           H  
HETATM  108  H32 UNL     1       2.611  -3.157  -1.676  1.00  0.00           H  
HETATM  109  H33 UNL     1       3.564  -2.242  -0.522  1.00  0.00           H  
HETATM  110  H34 UNL     1       1.033  -1.229  -1.976  1.00  0.00           H  
HETATM  111  H35 UNL     1       1.880  -0.317  -0.680  1.00  0.00           H  
HETATM  112  H36 UNL     1       4.701  -0.357  -0.006  1.00  0.00           H  
HETATM  113  H37 UNL     1       3.948   1.214  -0.276  1.00  0.00           H  
HETATM  114  H38 UNL     1       6.120   2.173  -0.864  1.00  0.00           H  
HETATM  115  H39 UNL     1       6.184   1.433   0.802  1.00  0.00           H  
HETATM  116  H40 UNL     1       8.214   1.046  -0.373  1.00  0.00           H  
HETATM  117  H41 UNL     1       7.435   0.380  -1.808  1.00  0.00           H  
HETATM  118  H42 UNL     1       6.567  -1.579  -0.339  1.00  0.00           H  
HETATM  119  H43 UNL     1       8.241  -2.390   1.048  1.00  0.00           H  
HETATM  120  H44 UNL     1       9.579   0.428   0.909  1.00  0.00           H  
HETATM  121  H45 UNL     1       9.532  -0.727   2.279  1.00  0.00           H  
HETATM  122  H46 UNL     1      10.813  -1.325  -0.405  1.00  0.00           H  
HETATM  123  H47 UNL     1       9.984  -3.068   1.717  1.00  0.00           H  
HETATM  124  H48 UNL     1      11.400  -3.257  -0.573  1.00  0.00           H  
HETATM  125  H49 UNL     1      11.555  -3.183   3.319  1.00  0.00           H  
HETATM  126  H50 UNL     1      12.862  -3.234   2.113  1.00  0.00           H  
HETATM  127  H51 UNL     1      13.316  -1.065   2.927  1.00  0.00           H  
HETATM  128  H52 UNL     1      11.661   0.329   3.573  1.00  0.00           H  
HETATM  129  H53 UNL     1      11.905   0.462   1.297  1.00  0.00           H  
HETATM  130  H54 UNL     1      13.466  -2.072   0.376  1.00  0.00           H  
HETATM  131  H55 UNL     1      13.621   0.937  -0.149  1.00  0.00           H  
HETATM  132  H56 UNL     1      15.335   1.353  -2.102  1.00  0.00           H  
HETATM  133  H57 UNL     1      16.807   0.366  -2.041  1.00  0.00           H  
HETATM  134  H58 UNL     1      17.206   2.444   1.902  1.00  0.00           H  
HETATM  135  H59 UNL     1      18.626   4.437   2.078  1.00  0.00           H  
HETATM  136  H60 UNL     1      19.418   5.567   0.022  1.00  0.00           H  
HETATM  137  H61 UNL     1      18.809   4.730  -2.142  1.00  0.00           H  
HETATM  138  H62 UNL     1      17.381   2.724  -2.323  1.00  0.00           H  
CONECT    1    2   77   78   79
CONECT    2    3    4   36
CONECT    3   80   81   82
CONECT    4    5   83   84
CONECT    5    6
CONECT    6    7    7    8    9
CONECT    8   85
CONECT    9   10
CONECT   10   11   11   12   13
CONECT   12   86
CONECT   13   14
CONECT   14   15   87   88
CONECT   15   16   30   89
CONECT   16   17
CONECT   17   18   28   90
CONECT   18   19   27
CONECT   19   20   20   91
CONECT   20   21
CONECT   21   22   22   27
CONECT   22   23   24
CONECT   23   92   93
CONECT   24   25   25
CONECT   25   26   94
CONECT   26   27   27
CONECT   28   29   30   95
CONECT   29   96
CONECT   30   31   97
CONECT   31   32
CONECT   32   33   33   34   35
CONECT   34   98
CONECT   35   99
CONECT   36   37   38  100
CONECT   37  101
CONECT   38   39   39   40
CONECT   40   41  102
CONECT   41   42  103  104
CONECT   42   43  105  106
CONECT   43   44   44   45
CONECT   45   46  107
CONECT   46   47  108  109
CONECT   47   48  110  111
CONECT   48   49
CONECT   49   50   50   51
CONECT   51   52  112  113
CONECT   52   53  114  115
CONECT   53   54  116  117
CONECT   54   55   55  118
CONECT   55   56  119
CONECT   56   57  120  121
CONECT   57   58   63  122
CONECT   58   59   60  123
CONECT   59  124
CONECT   60   61  125  126
CONECT   61   62   63  127
CONECT   62  128
CONECT   63   64  129
CONECT   64   65   65  130
CONECT   65   66  131
CONECT   66   67   68   69
CONECT   69   70  132  133
CONECT   70   71
CONECT   71   72   72   76
CONECT   72   73  134
CONECT   73   74   74  135
CONECT   74   75  136
CONECT   75   76   76  137
CONECT   76  138
END
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SMILES for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)

CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC=CCC1C(O)CC(O)C1C=CC(F)(F)COC1=CC=CC=C1
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INCHI for HMDB0301648 ((5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA)

InChI=1S/C43H62F2N7O20P3S/c1-42(2,22-69-75(65,66)72-74(63,64)68-21-31-36(71-73(60,61)62)35(57)41(70-31)52-25-51-34-38(46)49-24-50-39(34)52)37(58)40(59)48-17-15-32(55)47-18-19-76-33(56)13-9-4-3-8-12-27-28(30(54)20-29(27)53)14-16-43(44,45)23-67-26-10-6-5-7-11-26/h3,5-8,10-11,14,16,24-25,27-31,35-37,41,53-54,57-58H,4,9,12-13,15,17-23H2,1-2H3,(H,47,55)(H,48,59)(H,63,64)(H,65,66)(H2,46,49,50)(H2,60,61,62)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-({7-[2-(3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl]hept-5-enoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidateHMDB
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-({7-[2-(3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl]hept-5-enoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidateHMDB
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-({7-[2-(3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl]hept-5-enoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acidHMDB
Chemical FormulaC43H62F2N7O20P3S
Average Molecular Weight1159.98
Monoisotopic Molecular Weight1159.295125918
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({7-[2-(3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl]hept-5-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({7-[2-(3,3-difluoro-4-phenoxybut-1-en-1-yl)-3,5-dihydroxycyclopentyl]hept-5-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC=CCC1C(O)CC(O)C1C=CC(F)(F)COC1=CC=CC=C1
InChI Identifier
InChI=1S/C43H62F2N7O20P3S/c1-42(2,22-69-75(65,66)72-74(63,64)68-21-31-36(71-73(60,61)62)35(57)41(70-31)52-25-51-34-38(46)49-24-50-39(34)52)37(58)40(59)48-17-15-32(55)47-18-19-76-33(56)13-9-4-3-8-12-27-28(30(54)20-29(27)53)14-16-43(44,45)23-67-26-10-6-5-7-11-26/h3,5-8,10-11,14,16,24-25,27-31,35-37,41,53-54,57-58H,4,9,12-13,15,17-23H2,1-2H3,(H,47,55)(H,48,59)(H,63,64)(H,65,66)(H2,46,49,50)(H2,60,61,62)
InChI KeyGSLXROZZPAZVPZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2,3,4-saturated fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Pentose monosaccharide
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Phenoxy compound
  • Phenol ether
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl aryl ether
  • Imidolactam
  • Benzenoid
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Cyclopentanol
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Cyclic alcohol
  • Azole
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Amino acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.25ALOGPS
logP-2.3ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area413.32 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity266.22 m³·mol⁻¹ChemAxon
Polarizability109.27 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+296.36832859911
AllCCS[M+H-H2O]+297.28932859911
AllCCS[M+Na]+295.20932859911
AllCCS[M+NH4]+295.47432859911
AllCCS[M-H]-291.5832859911
AllCCS[M+Na-2H]-296.79332859911
AllCCS[M+HCOO]-302.40732859911
DeepCCS[M+H]+306.39930932474
DeepCCS[M-H]-304.50330932474
DeepCCS[M-2H]-338.47130932474
DeepCCS[M+Na]+312.48730932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202213.4464 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.23 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2494.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid166.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid176.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid191.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid138.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid476.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid553.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)1076.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid962.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid608.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid881.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid370.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid311.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate477.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA317.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water155.9 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA 10V, Negative-QTOFsplash10-0006-9400000000-fc0f835f0c069bfb3a372021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA 20V, Negative-QTOFsplash10-0006-9000000000-82b0b88dac5e187c812f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA 40V, Negative-QTOFsplash10-0006-9000000000-1a3f3998b56afdb9124e2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA 10V, Positive-QTOFsplash10-03di-5900000000-57600810bbd14fc56c312021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA 20V, Positive-QTOFsplash10-000i-3900000000-97c3c390b49ccec2497f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5Z)-7-{2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoyl-CoA 40V, Positive-QTOFsplash10-0udi-1301109000-b660af8ea7c09cecd4aa2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Abe T, Fujino T, Fukuyama R, Minoshima S, Shimizu N, Toh H, Suzuki H, Yamamoto T: Human long-chain acyl-CoA synthetase: structure and chromosomal location. J Biochem. 1992 Jan;111(1):123-8. [PubMed:1607358 ]
  2. Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]