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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:54:16 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034109

Secondary Accession Numbers

HMDB34109

Metabolite Identification

Common Name

Frenolicin B

Description

Frenolicin B belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. Based on a literature review very few articles have been published on Frenolicin B.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0034109
     RDKit          3D
Frenolicin B
 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.9407   -2.7302    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -1.5693   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845   -1.2848    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -0.1245   -0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    1.0137   -0.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463    2.1076   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    3.4319   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    4.3059   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302    5.5312   -0.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695    3.5149    0.4053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4433    2.2150    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227    1.1434    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0907    0.0550   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898   -1.0710   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609   -2.1030   -1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3861   -1.0080   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -2.0503   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9176   -3.2062   -0.9193 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734   -1.9025    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -0.7709    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442    0.2449    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253    0.1572    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8934    1.2604    0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    2.2827    1.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5938   -3.6635   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -2.7451    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0473   -2.6641    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2338   -1.8719   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9422   -0.6456   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380   -0.9144    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -2.1830    0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231   -0.4114   -1.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854    2.1393   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.4011    0.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612    3.7271   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333    2.1701    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874   -3.5365   -1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -2.7338   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0519   -0.6749    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4787    1.1636    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 13  4  1  0
 22 16  1  0
 11  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END


  Mrv0541 05061307352D          

 24 27  0  0  0  0            999 V2000
    2.4950   -2.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455   -1.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5828    2.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7770    2.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8323    1.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7454    1.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208    1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2761    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5521   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4968    0.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373    1.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1083    0.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8588    1.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150    1.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141    0.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5257   -0.0498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2280    2.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655    2.6634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1637   -0.4820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7463    0.0492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454    2.1621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 15  1  0  0  0  0
 19  9  1  0  0  0  0
 20 12  2  0  0  0  0
 21 16  2  0  0  0  0
 22 17  2  0  0  0  0
 23 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034109

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(C=CC=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-2-4-10-14-15(18-11(23-10)7-12(20)24-18)16(21)8-5-3-6-9(19)13(8)17(14)22/h3,5-6,10-11,18-19H,2,4,7H2,1H3

> <INCHI_KEY>
AVCPRTNVVRPELB-UHFFFAOYSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.17257602842693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.4245802486666665

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.412286959207568

> <JCHEM_PKA_STRONGEST_BASIC>
-4.222703861569621

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
83.38589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034109
     RDKit          3D
Frenolicin B
 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.9407   -2.7302    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -1.5693   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845   -1.2848    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -0.1245   -0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    1.0137   -0.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463    2.1076   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    3.4319   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    4.3059   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302    5.5312   -0.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695    3.5149    0.4053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4433    2.2150    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227    1.1434    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0907    0.0550   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898   -1.0710   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609   -2.1030   -1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3861   -1.0080   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -2.0503   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9176   -3.2062   -0.9193 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734   -1.9025    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -0.7709    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442    0.2449    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253    0.1572    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8934    1.2604    0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    2.2827    1.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5938   -3.6635   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -2.7451    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0473   -2.6641    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2338   -1.8719   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9422   -0.6456   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380   -0.9144    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -2.1830    0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231   -0.4114   -1.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854    2.1393   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.4011    0.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612    3.7271   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333    2.1701    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874   -3.5365   -1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -2.7338   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0519   -0.6749    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4787    1.1636    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 13  4  1  0
 22 16  1  0
 11  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.657  -4.312   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.192  -2.844   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.421   3.980   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.230  -1.707   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.917   4.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.887   2.512   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.391   2.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.879   3.173   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.849   1.375   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.764  -0.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.794   1.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.563   3.726   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.345   1.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.802   0.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.336   2.367   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.375   3.504   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.306   0.568   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.832   2.697   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.315  -0.093   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.426   4.764   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.909   4.972   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.772  -0.900   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.260   0.092   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.071   4.036   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    4                                                       
CONECT    3    5    6                                                       
CONECT    4    2   10                                                       
CONECT    5    3    8                                                       
CONECT    6    3    9                                                       
CONECT    7   11   12                                                       
CONECT    8    5   13   16                                                  
CONECT    9    6   13   19                                                  
CONECT   10    4   14   23                                                  
CONECT   11    7   18   23                                                  
CONECT   12    7   20   24                                                  
CONECT   13    8    9   17                                                  
CONECT   14   10   15   17                                                  
CONECT   15   14   16   18                                                  
CONECT   16    8   15   21                                                  
CONECT   17   13   14   22                                                  
CONECT   18   11   15   24                                                  
CONECT   19    9                                                            
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   10   11                                                       
CONECT   24   12   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0034109
HETATM    1  C1  UNL     1      -3.941  -2.730   0.325  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.327  -1.569  -0.432  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.984  -1.285   0.158  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.330  -0.125  -0.572  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.110   1.014  -0.467  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.346   2.108  -0.619  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.055   3.432  -0.504  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.911   4.306  -0.164  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.830   5.531  -0.350  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.069   3.515   0.405  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.443   2.215   0.639  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.523   1.143   0.438  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.091   0.055  -0.158  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.990  -1.071  -0.441  1.00  0.00           C  
HETATM   15  O4  UNL     1       0.561  -2.103  -1.016  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.386  -1.008  -0.062  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.240  -2.050  -0.317  1.00  0.00           C  
HETATM   18  O5  UNL     1       2.918  -3.206  -0.919  1.00  0.00           O  
HETATM   19  C14 UNL     1       4.573  -1.902   0.085  1.00  0.00           C  
HETATM   20  C15 UNL     1       5.021  -0.771   0.707  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.144   0.245   0.944  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.825   0.157   0.573  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.893   1.260   0.835  1.00  0.00           C  
HETATM   24  O6  UNL     1       2.371   2.283   1.416  1.00  0.00           O  
HETATM   25  H1  UNL     1      -3.594  -3.663  -0.172  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.509  -2.745   1.341  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.047  -2.664   0.359  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.234  -1.872  -1.495  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.942  -0.646  -0.330  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.138  -0.914   1.211  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.358  -2.183   0.201  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.323  -0.411  -1.651  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.685   2.139  -1.486  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.794   3.401   0.346  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.561   3.727  -1.439  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.033   2.170   1.551  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.087  -3.537  -1.277  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.274  -2.734  -0.114  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.052  -0.675   1.010  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.479   1.164   1.443  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   13   32
CONECT    5    6
CONECT    6    7   11   33
CONECT    7    8   34   35
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   36
CONECT   12   13   13   23
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   17   22
CONECT   17   18   19
CONECT   18   37
CONECT   19   20   20   38
CONECT   20   21   39
CONECT   21   22   22   40
CONECT   22   23
CONECT   23   24   24
END

HMDB0034109
     RDKit          3D
Frenolicin B
 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.9407   -2.7302    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3266   -1.5693   -0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845   -1.2848    0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -0.1245   -0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    1.0137   -0.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463    2.1076   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553    3.4319   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112    4.3059   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8302    5.5312   -0.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695    3.5149    0.4053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4433    2.2150    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227    1.1434    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0907    0.0550   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898   -1.0710   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609   -2.1030   -1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3861   -1.0080   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -2.0503   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9176   -3.2062   -0.9193 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734   -1.9025    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -0.7709    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442    0.2449    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253    0.1572    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8934    1.2604    0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    2.2827    1.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5938   -3.6635   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -2.7451    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0473   -2.6641    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2338   -1.8719   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9422   -0.6456   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1380   -0.9144    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -2.1830    0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231   -0.4114   -1.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854    2.1393   -1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    3.4011    0.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612    3.7271   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333    2.1701    1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874   -3.5365   -1.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -2.7338   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0519   -0.6749    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4787    1.1636    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 13  4  1  0
 22 16  1  0
 11  6  1  0
 23 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
AM 3867I	HMDB
Antibiotic am 3867I	HMDB
Antibiotic ucf76 C	HMDB
UCF76 C	HMDB

Chemical Formula

C₁₈H₁₆O₆

Average Molecular Weight

328.316

Monoisotopic Molecular Weight

328.094688244

IUPAC Name

4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

Traditional Name

4-hydroxy-17-propyl-12,16-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

CAS Registry Number

68930-68-7

SMILES

CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C18H16O6/c1-2-4-10-14-15(18-11(23-10)7-12(20)24-18)16(21)8-5-3-6-9(19)13(8)17(14)22/h3,5-6,10-11,18-19H,2,4,7H2,1H3

InChI Key

AVCPRTNVVRPELB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Furopyran
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Gamma butyrolactone
Benzenoid
Pyran
Tetrahydrofuran
Furan
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034109)
Cell membrane (HMDB: HMDB0034109)

Source

Exogenous

Exogenous (HMDB: HMDB0034109)

Food

Food (HMDB: HMDB0034109)

Endogenous

Plant

Plant (HMDB: HMDB0034109)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034109)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	157 - 159 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.42	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.39 m³·mol⁻¹	ChemAxon
Polarizability	33.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.944	31661259
DarkChem	[M-H]-	170.788	31661259
DeepCCS	[M+H]+	175.077	30932474
DeepCCS	[M-H]-	172.719	30932474
DeepCCS	[M-2H]-	206.358	30932474
DeepCCS	[M+Na]+	181.585	30932474
AllCCS	[M+H]+	176.7	32859911
AllCCS	[M+H-H2O]+	173.5	32859911
AllCCS	[M+NH4]+	179.7	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	179.7	32859911
AllCCS	[M+HCOO]-	179.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Frenolicin B	CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(C=CC=C1O)C2=O	4255.2	Standard polar	33892256
Frenolicin B	CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(C=CC=C1O)C2=O	2711.8	Standard non polar	33892256
Frenolicin B	CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(C=CC=C1O)C2=O	2847.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Frenolicin B,1TMS,isomer #1	CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1C2=O	2915.2	Semi standard non polar	33892256
Frenolicin B,1TBDMS,isomer #1	CCCC1OC2CC(=O)OC2C2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1C2=O	3144.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Frenolicin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kbo-3191000000-2e243a2dcbb2c4eee0f7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Frenolicin B GC-MS (1 TMS) - 70eV, Positive	splash10-006x-2009000000-463085069ef510ea2dee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Frenolicin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 10V, Positive-QTOF	splash10-004i-1029000000-f6a29c2a003772ea1003	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 20V, Positive-QTOF	splash10-00b9-1291000000-a09b96a34550e3a95139	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 40V, Positive-QTOF	splash10-0udi-9020000000-f040d477e039995a01d0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 10V, Negative-QTOF	splash10-004i-0019000000-b4b0a43a7ce371601471	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 20V, Negative-QTOF	splash10-0a7i-1092000000-06e10db3fdd1353b60b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 40V, Negative-QTOF	splash10-06s6-9050000000-eee92b24bfc37b41d431	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 10V, Negative-QTOF	splash10-004i-0009000000-0447e52768356e443881	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 20V, Negative-QTOF	splash10-004i-0029000000-cbddb9c901668d3a02f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 40V, Negative-QTOF	splash10-06ry-6292000000-702f069189035eb30a4b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 10V, Positive-QTOF	splash10-004i-0009000000-469c8ff76acf89a49db2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 20V, Positive-QTOF	splash10-004i-0029000000-32ea2728606b44ee80c7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frenolicin B 40V, Positive-QTOF	splash10-052r-3952000000-f3dcfd28748a51d242d5	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012376

KNApSAcK ID

C00018203

Chemspider ID

28587202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Frenolicin B

METLIN ID

Not Available

PubChem Compound

13337184

PDB ID

Not Available

ChEBI ID

48201

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Frenolicin B (HMDB0034109)

MOL for HMDB0034109 (Frenolicin B)

3D MOL for HMDB0034109 (Frenolicin B)

3D SDF for HMDB0034109 (Frenolicin B)

3D-SDF for HMDB0034109 (Frenolicin B)

PDB for HMDB0034109 (Frenolicin B)

3D PDB for HMDB0034109 (Frenolicin B)

SMILES for HMDB0034109 (Frenolicin B)

INCHI for HMDB0034109 (Frenolicin B)

Structure for HMDB0034109 (Frenolicin B)

3D Structure for HMDB0034109 (Frenolicin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra