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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-04-30 16:48:31 UTC

HMDB ID

HMDB0001347

Secondary Accession Numbers

HMDB0004196
HMDB01347
HMDB04196

Metabolite Identification

Common Name

Isopentenyl pyrophosphate

Description

Isopentenyl pyrophosphate, also known as IPP or delta(3)-isopentenyl-PP, belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Isopentenyl pyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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


  Mrv1652309042000212D          

 14 13  0  0  0  0            999 V2000
   16.3566   -5.2503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9279   -5.2503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6422   -4.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2134   -4.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0711   -4.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7856   -5.2503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4990   -5.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7845   -4.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0699   -5.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7844   -4.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0711   -4.8377    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.0712   -5.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6422   -4.8377    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.6422   -5.6629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  3  2  0  0  0  0
 11  5  2  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 11  6  1  0  0  0  0
  1 11  1  0  0  0  0
  2  4  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 13  2  1  0  0  0  0
 13  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001347

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)CCOP(O)(=O)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)

> <INCHI_KEY>
NUHSROFQTUXZQQ-UHFFFAOYSA-N

> <FORMULA>
C5H12O7P2

> <MOLECULAR_WEIGHT>
246.0921

> <EXACT_MASS>
246.005825762

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.011958475186823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
0.19933072100000007

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.219951501702814

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7784542453586973

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
48.2068

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isopentenyl-diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      30.532  -9.801   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.865  -9.801   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.199  -7.491   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      26.532  -9.030   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      31.866  -7.490   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.200  -9.801   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      25.198  -9.801   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.864  -9.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.530  -9.801   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.864  -7.491   0.000  0.00  0.00           C+0
HETATM   11  P   UNK     0      31.866  -9.030   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0      31.866 -10.570   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      29.199  -9.030   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      29.199 -10.571   0.000  0.00  0.00           O+0
CONECT    1   11   13                                                       
CONECT    2    4   13                                                       
CONECT    3   13                                                            
CONECT    4    2    7                                                       
CONECT    5   11                                                            
CONECT    6   11                                                            
CONECT    7    4    8                                                       
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12    6    1                                             
CONECT   12   11                                                            
CONECT   13    3   14    2    1                                             
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-3-butenyl pyrophosphate	ChEBI
3-Methylbut-3-en-1-yl trihydrogen diphosphate	ChEBI
3-Methylbut-3-enyl phosphono hydrogen phosphate	ChEBI
delta-3-Isopentenyl pyrophosphate	ChEBI
delta3-Isopentenyl diphosphate	ChEBI
delta3-Methyl-3-butenyl diphosphate	ChEBI
Diphosphoric acid mono(3-methyl-3-butenyl) ester	ChEBI
IPP	ChEBI
IPPP	ChEBI
mono(3-Methyl-3-butenyl) diphosphate	ChEBI
3-Methyl-3-butenyl pyrophosphoric acid	Generator
3-Methylbut-3-en-1-yl trihydrogen diphosphoric acid	Generator
3-Methylbut-3-enyl phosphono hydrogen phosphoric acid	Generator
delta-3-Isopentenyl pyrophosphoric acid	Generator
Δ-3-isopentenyl pyrophosphate	Generator
Δ-3-isopentenyl pyrophosphoric acid	Generator
delta3-Isopentenyl diphosphoric acid	Generator
Δ3-isopentenyl diphosphate	Generator
Δ3-isopentenyl diphosphoric acid	Generator
delta3-Methyl-3-butenyl diphosphoric acid	Generator
Δ3-methyl-3-butenyl diphosphate	Generator
Δ3-methyl-3-butenyl diphosphoric acid	Generator
Diphosphate mono(3-methyl-3-butenyl) ester	Generator
mono(3-Methyl-3-butenyl) diphosphoric acid	Generator
Isopentenyl pyrophosphoric acid	Generator
delta(3)-Isopentenyl-PP	HMDB
delta-3-Isopentenyl pyrophosphat	HMDB
IPR	HMDB
Isopentenyl diphosphate	HMDB
Isopentenyl-PP	HMDB
Isopentenyl pyrophosphate, 4-(14)C-labeled	HMDB

Chemical Formula

C₅H₁₂O₇P₂

Average Molecular Weight

246.0921

Monoisotopic Molecular Weight

246.005825762

IUPAC Name

({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

Traditional Name

isopentenyl-diphosphate

CAS Registry Number

358-71-4

SMILES

CC(=C)CCOP(O)(=O)OP(O)(O)=O

InChI Identifier

InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)

InChI Key

NUHSROFQTUXZQQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Isoprenoid phosphates

Direct Parent

Isoprenoid phosphates

Alternative Parents

Substituents

Organic pyrophosphate
Isoprenoid phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

prenol phosphate (CHEBI:16584 )
C5 isoprenoids (hemiterpenes) (C00129 )
C5 isoprenoids (hemiterpenes) (LMPR01010008 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	141.708	30932474
[M-H]-	Not Available	141.708	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000246

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.69 g/L	ALOGPS
logP	0.04	ALOGPS
logP	0.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	48.21 m³·mol⁻¹	ChemAxon
Polarizability	19.01 Å³	ChemAxon
Number of Rings	0	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]+	156.727	31661259
DarkChem	[M-H]-	148.886	31661259
AllCCS	[M+H]+	153.643	32859911
AllCCS	[M-H]-	145.319	32859911
DeepCCS	[M+H]+	136.003	30932474
DeepCCS	[M-H]-	132.215	30932474
DeepCCS	[M-2H]-	170.051	30932474
DeepCCS	[M+Na]+	145.39	30932474
AllCCS	[M+H]+	153.6	32859911
AllCCS	[M+H-H2O]+	150.2	32859911
AllCCS	[M+NH4]+	156.8	32859911
AllCCS	[M+Na]+	157.7	32859911
AllCCS	[M-H]-	145.3	32859911
AllCCS	[M+Na-2H]-	146.6	32859911
AllCCS	[M+HCOO]-	148.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.03 minutes	32390414
Predicted by Siyang on May 30, 2022	9.679 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	422.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	625.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	296.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	62.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	269.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	410.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	180.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	629.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	276.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	622.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	679.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	392.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopentenyl pyrophosphate	CC(=C)CCOP(O)(=O)OP(O)(O)=O	3101.3	Standard polar	33892256
Isopentenyl pyrophosphate	CC(=C)CCOP(O)(=O)OP(O)(O)=O	1662.2	Standard non polar	33892256
Isopentenyl pyrophosphate	CC(=C)CCOP(O)(=O)OP(O)(O)=O	1917.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isopentenyl pyrophosphate,1TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O	1868.5	Semi standard non polar	33892256
Isopentenyl pyrophosphate,1TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O	1697.9	Standard non polar	33892256
Isopentenyl pyrophosphate,1TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O	2676.0	Standard polar	33892256
Isopentenyl pyrophosphate,1TMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C	1836.0	Semi standard non polar	33892256
Isopentenyl pyrophosphate,1TMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C	1683.6	Standard non polar	33892256
Isopentenyl pyrophosphate,1TMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C	2734.0	Standard polar	33892256
Isopentenyl pyrophosphate,2TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	1881.8	Semi standard non polar	33892256
Isopentenyl pyrophosphate,2TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	1801.3	Standard non polar	33892256
Isopentenyl pyrophosphate,2TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2390.2	Standard polar	33892256
Isopentenyl pyrophosphate,2TMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1887.7	Semi standard non polar	33892256
Isopentenyl pyrophosphate,2TMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1794.5	Standard non polar	33892256
Isopentenyl pyrophosphate,2TMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2410.1	Standard polar	33892256
Isopentenyl pyrophosphate,3TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1931.5	Semi standard non polar	33892256
Isopentenyl pyrophosphate,3TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1884.9	Standard non polar	33892256
Isopentenyl pyrophosphate,3TMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2143.9	Standard polar	33892256
Isopentenyl pyrophosphate,1TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2099.3	Semi standard non polar	33892256
Isopentenyl pyrophosphate,1TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	1906.9	Standard non polar	33892256
Isopentenyl pyrophosphate,1TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2839.7	Standard polar	33892256
Isopentenyl pyrophosphate,1TBDMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2089.1	Semi standard non polar	33892256
Isopentenyl pyrophosphate,1TBDMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	1910.4	Standard non polar	33892256
Isopentenyl pyrophosphate,1TBDMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2899.1	Standard polar	33892256
Isopentenyl pyrophosphate,2TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2309.8	Semi standard non polar	33892256
Isopentenyl pyrophosphate,2TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2179.0	Standard non polar	33892256
Isopentenyl pyrophosphate,2TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2633.7	Standard polar	33892256
Isopentenyl pyrophosphate,2TBDMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2316.5	Semi standard non polar	33892256
Isopentenyl pyrophosphate,2TBDMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2137.3	Standard non polar	33892256
Isopentenyl pyrophosphate,2TBDMS,isomer #2	C=C(C)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2665.2	Standard polar	33892256
Isopentenyl pyrophosphate,3TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2528.1	Semi standard non polar	33892256
Isopentenyl pyrophosphate,3TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2358.6	Standard non polar	33892256
Isopentenyl pyrophosphate,3TBDMS,isomer #1	C=C(C)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2450.2	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04714

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

DELTA3-ISOPENTENYL-PP

BiGG ID

33956

Wikipedia Link

Isopentenyl pyrophosphate

METLIN ID

6181

PubChem Compound

1195

PDB ID

Not Available

ChEBI ID

16584

Food Biomarker Ontology

Not Available

VMH ID

IPDP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kao, Chai-Lin; Kittleman, William; Zhang, Hua; Seto, Haruo; Liu, Hung-Wen. Stereochemical Analysis of Isopentenyl Diphosphate Isomerase Type II from Staphylococcus aureus Using Chemically Synthesized (S)- and (R)-[2-2H]Isopentenyl Diphosphates. Org Lett. 2005 Dec 8;7(25):5677-80.

Material Safety Data Sheet (MSDS)

Not Available

General References

Daubenberger CA, Salomon M, Vecino W, Hubner B, Troll H, Rodriques R, Patarroyo ME, Pluschke G: Functional and structural similarity of V gamma 9V delta 2 T cells in humans and Aotus monkeys, a primate infection model for Plasmodium falciparum malaria. J Immunol. 2001 Dec 1;167(11):6421-30. [PubMed:11714808 ]

Enzymes

Enzyme Details

1. Geranylgeranyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name:: GGPS1
Uniprot ID:: O95749
Molecular weight:: 34870.625

Reactions

Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PP	details
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphate	details
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranylgeranyl-PP	details

Enzyme Details

2. Farnesyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:: FDPS
Uniprot ID:: P14324
Molecular weight:: 48275.03

Reactions

Dimethylallylpyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranyl-PP	details
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphate	details

Enzyme Details

3. Diphosphomevalonate decarboxylase

General function:: Involved in ATP binding
Specific function:: Performs the first committed step in the biosynthesis of isoprenes.
Gene Name:: MVD
Uniprot ID:: P53602
Molecular weight:: 43404.125

Reactions

Adenosine triphosphate + (R)-5-Diphosphomevalonic acid → ADP + Phosphate + Isopentenyl pyrophosphate + CO(2)	details
Adenosine triphosphate + (R)-5-Diphosphomevalonic acid → ADP + Phosphate + Isopentenyl pyrophosphate + Carbon dioxide	details

Enzyme Details

4. Isopentenyl-diphosphate Delta-isomerase 2

General function:: Lipid transport and metabolism
Specific function:: Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
Gene Name:: IDI2
Uniprot ID:: Q9BXS1
Molecular weight:: 26752.33

Reactions

Isopentenyl pyrophosphate → Dimethylallylpyrophosphate	details

Enzyme Details

5. Isopentenyl-diphosphate Delta-isomerase 1

General function:: Involved in isopentenyl-diphosphate delta-isomerase activity
Specific function:: Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
Gene Name:: IDI1
Uniprot ID:: Q13907
Molecular weight:: 32485.165

Reactions

Isopentenyl pyrophosphate → Dimethylallylpyrophosphate	details

Enzyme Details

6. tRNA isopentenyltransferase 1 variant

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: TRIT1
Uniprot ID:: Q53F11
Molecular weight:: 52727.9

Enzyme Details

7. Decaprenyl-diphosphate synthase subunit 2

General function:: Not Available
Specific function:: Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:: PDSS2
Uniprot ID:: Q86YH6
Molecular weight:: 44128.17

Reactions

Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + all-trans-Decaprenyl diphosphate	details

Enzyme Details

8. Decaprenyl-diphosphate synthase subunit 1

General function:: Not Available
Specific function:: Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:: PDSS1
Uniprot ID:: Q5T2R2
Molecular weight:: 46260.6

Reactions

Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + all-trans-Decaprenyl diphosphate	details

Showing metabocard for Isopentenyl pyrophosphate (HMDB0001347)

MOL for HMDB0001347 (Isopentenyl pyrophosphate)

3D MOL for HMDB0001347 (Isopentenyl pyrophosphate)

3D SDF for HMDB0001347 (Isopentenyl pyrophosphate)

3D-SDF for HMDB0001347 (Isopentenyl pyrophosphate)

PDB for HMDB0001347 (Isopentenyl pyrophosphate)

3D PDB for HMDB0001347 (Isopentenyl pyrophosphate)

SMILES for HMDB0001347 (Isopentenyl pyrophosphate)

INCHI for HMDB0001347 (Isopentenyl pyrophosphate)

Structure for HMDB0001347 (Isopentenyl pyrophosphate)

3D Structure for HMDB0001347 (Isopentenyl pyrophosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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