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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:45:28 UTC

HMDB ID

HMDB0001120

Secondary Accession Numbers

HMDB0002101
HMDB01120
HMDB02101

Metabolite Identification

Common Name

Dimethylallylpyrophosphate

Description

Dimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphoric acid, 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. Dimethylallylpyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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


  Mrv1652306252021212D          

 14 13  0  0  0  0            999 V2000
10023.959510023.0458    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10024.683410022.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.244810022.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10023.549010023.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10024.374010023.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.397210023.0581    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10022.529810023.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.984610023.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.110810022.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10025.809610023.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.814910022.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.099810023.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.384910022.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.099810023.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001120

> <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/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)

> <INCHI_KEY>
CBIDRCWHNCKSTO-UHFFFAOYSA-N

> <FORMULA>
C5H12O7P2

> <MOLECULAR_WEIGHT>
246.0921

> <EXACT_MASS>
246.005825762

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.189525286748115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
0.2973045106666672

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2043412500331905

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.767219152287395

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
49.1253

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethylallyl diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JUN-20         0                                  
HETATM    1  P   UNK     0    8711.3918709.686   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0    8712.7428708.940   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8710.0578708.917   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8710.6258711.019   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8712.1658711.019   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0    8714.0758709.708   0.000  0.00  0.00           P+0
HETATM    7  C   UNK     0    8708.7228709.686   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8713.3058711.042   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8715.4078708.940   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8714.8458711.042   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8707.3888708.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8706.0538709.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8704.7188708.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8706.0538711.227   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    8    9   10                                             
CONECT    7    3   11                                                       
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
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
2-Isopentenyl diphosphate	ChEBI
3,3-Dimethylallyl pyrophosphate	ChEBI
3-Methylbut-2-enyl phosphono hydrogen phosphate	ChEBI
delta-Prenyl diphosphate	ChEBI
delta2-Isopentenyl diphosphate	ChEBI
Dimethylallyl diphosphate	ChEBI
Dimethylallyl pyrophosphate	ChEBI
DMAPP	ChEBI
Monoprenyl diphosphate	ChEBI
Prenol pyrophosphate	ChEBI
Prenyl diphosphate	Kegg
2-Isopentenyl diphosphoric acid	Generator
3,3-Dimethylallyl pyrophosphoric acid	Generator
3-Methylbut-2-enyl phosphono hydrogen phosphoric acid	Generator
delta-Prenyl diphosphoric acid	Generator
Δ-prenyl diphosphate	Generator
Δ-prenyl diphosphoric acid	Generator
delta2-Isopentenyl diphosphoric acid	Generator
Δ2-isopentenyl diphosphate	Generator
Δ2-isopentenyl diphosphoric acid	Generator
Dimethylallyl diphosphoric acid	Generator
Dimethylallyl pyrophosphoric acid	Generator
Monoprenyl diphosphoric acid	Generator
Prenol pyrophosphoric acid	Generator
Prenyl diphosphoric acid	Generator
Dimethylallylpyrophosphoric acid	Generator
1,1-Dimethyl-4-phenylpiperazinium iodide	HMDB
3-Methyl-2-buten-1-ol pyrophosphate	HMDB
3-Methyl-2-buten-1-ol trihydrogen pyrophosphate	HMDB
3-Methyl-2-butenyl pyrophosphate	HMDB
3-Methylbut-2-enyl pyrophosphate	HMDB
Delta2-Isopentenyl-diphosphate	HMDB
Dimethylallyl-diphosphate	HMDB
Dimethylallyl-PP	HMDB
Dimethylallyl-ppi	HMDB
Dimethylallyl-pyrophosphate	HMDB
Diphosphoric acid mono(3-methyl-2-butenyl) ester	HMDB
DMPP	HMDB
IPE	HMDB
Prenyl-diphosphate	HMDB
3,3-Dimethylallyl pyrophosphate, (14)C-labeled	HMDB
DMADP CPD	HMDB
3-Methyl-2-butenyl trihydrogen diphosphate	HMDB
Dimethylallylpyrophosphate	HMDB
gamma,gamma-Dimethylallyl pyrophosphate	HMDB
γ,γ-Dimethylallyl pyrophosphate	HMDB

Chemical Formula

C₅H₁₂O₇P₂

Average Molecular Weight

246.0921

Monoisotopic Molecular Weight

246.005825762

IUPAC Name

({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

Traditional Name

dimethylallyl diphosphate

CAS Registry Number

358-72-5

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/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)

InChI Key

CBIDRCWHNCKSTO-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:16057 )
C5 isoprenoids (hemiterpenes) (C00235 )
C5 isoprenoids (hemiterpenes) (LMPR01010001 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	234 - 238 °C	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]-	Not Available	143.096	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000238

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.54 g/L	ALOGPS
logP	0.3	ALOGPS
logP	0.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.77	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	5	ChemAxon
Refractivity	49.13 m³·mol⁻¹	ChemAxon
Polarizability	19.19 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]+	156.653	31661259
DarkChem	[M-H]-	148.628	31661259
AllCCS	[M+H]+	153.329	32859911
AllCCS	[M-H]-	145.676	32859911
DeepCCS	[M+H]+	135.3	30932474
DeepCCS	[M-H]-	131.472	30932474
DeepCCS	[M-2H]-	169.171	30932474
DeepCCS	[M+Na]+	144.561	30932474
AllCCS	[M+H]+	153.3	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	156.5	32859911
AllCCS	[M+Na]+	157.4	32859911
AllCCS	[M-H]-	145.7	32859911
AllCCS	[M+Na-2H]-	147.0	32859911
AllCCS	[M+HCOO]-	148.5	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.	4.24 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7507 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	433.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	690.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	303.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	58.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.4 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	346.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	308.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	636.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	284.0 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	565.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	652.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	308.6 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	391.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dimethylallylpyrophosphate	CC(C)=CCOP(O)(=O)OP(O)(O)=O	3264.5	Standard polar	33892256
Dimethylallylpyrophosphate	CC(C)=CCOP(O)(=O)OP(O)(O)=O	1661.1	Standard non polar	33892256
Dimethylallylpyrophosphate	CC(C)=CCOP(O)(=O)OP(O)(O)=O	1963.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dimethylallylpyrophosphate,1TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O	1934.5	Semi standard non polar	33892256
Dimethylallylpyrophosphate,1TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O	1788.9	Standard non polar	33892256
Dimethylallylpyrophosphate,1TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O	2644.6	Standard polar	33892256
Dimethylallylpyrophosphate,1TMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C	1913.0	Semi standard non polar	33892256
Dimethylallylpyrophosphate,1TMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C	1775.7	Standard non polar	33892256
Dimethylallylpyrophosphate,1TMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C	2675.7	Standard polar	33892256
Dimethylallylpyrophosphate,2TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	1942.1	Semi standard non polar	33892256
Dimethylallylpyrophosphate,2TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	1857.7	Standard non polar	33892256
Dimethylallylpyrophosphate,2TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2352.1	Standard polar	33892256
Dimethylallylpyrophosphate,2TMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1949.6	Semi standard non polar	33892256
Dimethylallylpyrophosphate,2TMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1848.6	Standard non polar	33892256
Dimethylallylpyrophosphate,2TMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2359.9	Standard polar	33892256
Dimethylallylpyrophosphate,3TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1964.7	Semi standard non polar	33892256
Dimethylallylpyrophosphate,3TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1913.7	Standard non polar	33892256
Dimethylallylpyrophosphate,3TMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2115.5	Standard polar	33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2176.2	Semi standard non polar	33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	1977.1	Standard non polar	33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2795.3	Standard polar	33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2159.4	Semi standard non polar	33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	1976.7	Standard non polar	33892256
Dimethylallylpyrophosphate,1TBDMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2831.3	Standard polar	33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2355.7	Semi standard non polar	33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2220.0	Standard non polar	33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #1	CC(C)=CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2584.5	Standard polar	33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2366.6	Semi standard non polar	33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2184.5	Standard non polar	33892256
Dimethylallylpyrophosphate,2TBDMS,isomer #2	CC(C)=CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2601.7	Standard polar	33892256
Dimethylallylpyrophosphate,3TBDMS,isomer #1	CC(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	2546.4	Semi standard non polar	33892256
Dimethylallylpyrophosphate,3TBDMS,isomer #1	CC(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	2364.8	Standard non polar	33892256
Dimethylallylpyrophosphate,3TBDMS,isomer #1	CC(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	2417.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Skeletal Muscle

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

DB01785

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Dimethylallyl pyrophosphate

METLIN ID

6016

PubChem Compound

647

PDB ID

Not Available

ChEBI ID

16057

Food Biomarker Ontology

Not Available

VMH ID

DMPP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Smith AS, Smid SD: Impaired capsaicin and neurokinin-evoked colonic motility in inflammatory bowel disease. J Gastroenterol Hepatol. 2005 May;20(5):697-704. [PubMed:15853981 ]

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

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

Enzyme Details

3. 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

4. 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

5. tRNA dimethylallyltransferase, mitochondrial

General function:: Not Available
Specific function:: Catalyzes the transfer of a dimethylallyl group onto the adenine at position 37 of both cytosolic and mitochondrial tRNAs, leading to the formation of N6-(dimethylallyl)adenosine (i(6)A).
Gene Name:: TRIT1
Uniprot ID:: Q9H3H1
Molecular weight:: 52724.84

Reactions

Dimethylallylpyrophosphate + tRNA → Pyrophosphate + tRNA containing 6-dimethylallyladenosine	details
Dimethylallylpyrophosphate + tRNA → Pyrophosphate + tRNA containing 6-isopentenyladenosine	details

Showing metabocard for Dimethylallylpyrophosphate (HMDB0001120)

MOL for HMDB0001120 (Dimethylallylpyrophosphate)

3D MOL for HMDB0001120 (Dimethylallylpyrophosphate)

3D SDF for HMDB0001120 (Dimethylallylpyrophosphate)

3D-SDF for HMDB0001120 (Dimethylallylpyrophosphate)

PDB for HMDB0001120 (Dimethylallylpyrophosphate)

3D PDB for HMDB0001120 (Dimethylallylpyrophosphate)

SMILES for HMDB0001120 (Dimethylallylpyrophosphate)

INCHI for HMDB0001120 (Dimethylallylpyrophosphate)

Structure for HMDB0001120 (Dimethylallylpyrophosphate)

3D Structure for HMDB0001120 (Dimethylallylpyrophosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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