Mevalonic acid-5P (YMDB00181)

Identification

YMDB ID

YMDB00181

Name

Mevalonic acid-5P

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Mevalonic acid-5P, also known as mevalonate-5P or 5-phosphomevalonate, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Mevalonic acid-5P is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Mevalonic acid-5P exists in all living species, ranging from bacteria to humans. Within yeast, mevalonic acid-5P participates in a number of enzymatic reactions. In particular, mevalonic acid-5P can be biosynthesized from mevalonic acid; which is catalyzed by the enzyme mevalonate kinase. In addition, mevalonic acid-5P can be converted into (S)-5-diphosphomevalonic acid through its interaction with the enzyme phosphomevalonate kinase. In yeast, mevalonic acid-5P is involved in the metabolic pathway called terpenoid backbone biosynthesis pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(R)-5-phosphomevalonate
(R)-5-phosphomevalonic acid
(R)-5-phosphomevaloonate
(R)-5-phosphomevaloonic acid
(R)-mevalonic acid 5-phosphate
5-phosphomevalonate
mevalonate-5-p
mevalonate-5-phosphate
mevalonate-5P
mevalonate-p
p-mevalonate
(R)-Mevalonate 5-phosphate
(R)-Mevalonic acid 5-phosphoric acid
5-Phosphomevalonic acid
Mevalonate 5-phosphate
Phosphomevalonate
Phosphomevalonic acid
Phosphomevalonic acid, (+-)-isomer
(3R)-3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
Mevalonic acid phosphate
Mevalonic acid-5P

CAS number

73566-35-5

Weight

Average: 228.137
Monoisotopic: 228.039889282

InChI Key

OKZYCXHTTZZYSK-ZCFIWIBFSA-N

InChI

InChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1

IUPAC Name

(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid

Traditional IUPAC Name

mevalonate-5-phosphate

Chemical Formula

C₆H₁₃O₇P

SMILES

[H]OC(=O)C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])OP(=O)(O[H])O[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Short-chain hydroxy acid
Fatty acid
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:17436 )
carboxyalkyl phosphate (CHEBI:17436 )
Hydroxy fatty acids (LMFA01050415 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	19.9 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-1.2	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	45.38 m³·mol⁻¹	ChemAxon
Polarizability	19.23 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

Organoleptic Properties

Not Available

SMPDB Pathways

Cholesterol biosynthesis and metabolism CE(10:0)	PW002545
Cholesterol biosynthesis and metabolism CE(12:0)	PW002548
Cholesterol biosynthesis and metabolism CE(14:0)	PW002544
Cholesterol biosynthesis and metabolism CE(16:0)	PW002550
Cholesterol biosynthesis and metabolism CE(18:0)	PW002551

KEGG Pathways

Steroid biosynthesis	ec00100
Terpenoid backbone biosynthesis	ec00900

SMPDB Reactions

(R)-Mevalonic acid + Adenosine triphosphate → Mevalonic acid-5P + ADP

Adenosine triphosphate + Mevalonic acid-5P → ADP + 5-Diphosphomevalonic acid

KEGG Reactions

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0292-9600000000-a4f04a66624afb8d522a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9413000000-7329637530b2ddc29e0b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1960000000-a02358583ea07452bacf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-4900000000-ef07c3371552f7c1c11d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02ti-9800000000-bba2c1c56648b04a1fdd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-8960000000-de18bb77f2282c89d45a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-6dd83d59bdb427eeee24	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9c715a4954dce4d5a856	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01si-1940000000-c405e8487510c01d67be	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-9300000000-84bcd8640d320dd874e3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06ry-9200000000-6589ef1abdd604511639	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-5090000000-98125cefd75fccd3e564	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9020000000-74f440cb4e3ffa40388d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17436
HMDB ID	HMDB01343
Pubchem Compound ID	439400
Kegg ID	C01107
ChemSpider ID	388517
FOODB ID	FDB031001
Wikipedia	5-phosphomevalonate
BioCyc ID	CPD-499

Enzymes

Protein Details

1. Mevalonate kinase

General function:: Involved in ATP binding
Specific function:: RAR (regulation of autonomous replication) is a protein whose activity increases the mitotic stability of plasmids
Gene Name:: ERG12
Uniprot ID:: P07277
Molecular weight:: 48458.89844

Reactions

ATP + (R)-mevalonate → ADP + (R)-5-phosphomevalonate.

Protein Details

2. Phosphomevalonate kinase

General function:: Involved in ATP binding
Specific function:: ATP + (R)-5-phosphomevalonate = ADP + (R)-5- diphosphomevalonate
Gene Name:: ERG8
Uniprot ID:: P24521
Molecular weight:: 50454.39844

Reactions

ATP + (R)-5-phosphomevalonate → ADP + (R)-5-diphosphomevalonate.

Structure for #<Compound:0x051ead98>

Enzymes

Reactions

Reactions