ECMDB: 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate (ECMDB20020) (M2MDB000869)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (770)

Record Information

Version

2.0

Creation Date

2012-05-31 14:23:15 -0600

Update Date

2015-09-17 16:24:16 -0600

Secondary Accession Numbers

ECMDB20020

Identification

Name:

1-Hydroxy-2-methyl-2-butenyl 4-diphosphate

Description

1-hydroxy-2-methyl-2-butenyl 4-diphosphate is a member of the chemical class known as Organic Pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(E)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate
(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate
(E)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate
(e)-4-Hydroxy-3-methylbut 2-en-1-yl diphosphoric acid
(E)-4-Hydroxy-3-methylbut-2-en-1-yl diphosphate
(e)-4-Hydroxy-3-methylbut-2-en-1-yl diphosphoric acid
1-Hydroxy-2-methyl-2-butenyl 4-diphosphoric acid
Hmbdp
HMeBuPP

Chemical Formula:

C₅H₁₂O₈P₂

Weight:

Average: 262.0915
Monoisotopic: 262.000740384

InChI Key:

MDSIZRKJVDMQOQ-UHFFFAOYSA-N

InChI:

InChI=1S/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9)

CAS number:

Not Available

IUPAC Name:

{[hydroxy({[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxy})phosphoryl]oxy}phosphonic acid

Traditional IUPAC Name:

{hydroxy[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxyphosphoryl}oxyphosphonic acid

SMILES:

CC(CO)=CCOP(O)(=O)OP(O)(O)=O

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
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

prenol phosphate (CHEBI:15664 )
C5 isoprenoids (hemiterpenes) (LMPR01010009 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	7.16 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-0.98	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.9 m³·mol⁻¹	ChemAxon
Polarizability	20.3 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Metabolic pathways eco01100
Terpenoid backbone biosynthesis ec00900

EcoCyc Pathways:

methylerythritol phosphate pathway NONMEVIPP-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02a6-9480000000-679684fe1ec377d9cf57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014s-9200000000-d524050753c3abc5626a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ktr-9000000000-9a9df051848d50c79826	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0390000000-0df7e8040ad9397e5bf9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-77c42582a268dc85118e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8e4f15dd44340d0e5fd2	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15664
HMDB ID	Not Available
Pubchem Compound ID	786
Kegg ID	C11811
ChemSpider ID	4445244
Wikipedia ID	Not Available
BioCyc ID	HYDROXY-METHYL-BUTENYL-DIP
EcoCyc ID	HYDROXY-METHYL-BUTENYL-DIP
Ligand Expo	H6P

Enzymes

Protein Details

1. 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase

General function:: Involved in catalytic activity
Specific function:: Converts 2C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-2,4cPP) into 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate
Gene Name:: ispG
Uniprot ID:: P62620
Molecular weight:: 40683

Reactions

(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H(2)O + 2 oxidized ferredoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced ferredoxin.

Protein Details

2. 4-hydroxy-3-methylbut-2-enyl diphosphate reductase

General function:: Involved in isopentenyl diphosphate biosynthetic process, mevalonate-independent pathway
Specific function:: Converts 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). Is also involved in penicillin tolerance and control of the stringent response. Seems to directly or indirectly interact with relA to maintain it in an inactive form during normal growth
Gene Name:: ispH
Uniprot ID:: P62623
Molecular weight:: 34774

Reactions

Isopentenyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.
Dimethylallyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.

Protein Details

3. Flavodoxin-2

General function:: Involved in FMN binding
Specific function:: Low-potential electron donor to a number of redox enzymes (Potential)
Gene Name:: fldB
Uniprot ID:: P0ABY4
Molecular weight:: 19700

Protein Details

4. Flavodoxin-1

General function:: Involved in FMN binding
Specific function:: Low-potential electron donor to a number of redox enzymes (Potential). Involved in the reactivation of inactive cob(II)alamin in methionine synthase
Gene Name:: fldA
Uniprot ID:: P61949
Molecular weight:: 19737

1-Hydroxy-2-methyl-2-butenyl 4-diphosphate (ECMDB20020) (M2MDB000869)

Structure for #<Compound:0x7f674da8>

Enzymes

Reactions

Reactions