Cannabis Compound Database: Showing Compound Card for Presqualene diphosphate (CDB005314)

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Record Information

Version

1.0

Created at

2020-04-17 19:30:47 UTC

Updated at

2020-12-07 19:11:56 UTC

CannabisDB ID

CDB005314

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Presqualene diphosphate

Description

Presqualene diphosphate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Presqualene diphosphate is a moderately acidic compound (based on its pKa). Presqualene diphosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[(1S,2S,3S)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphate	ChEBI
[(1S,2S,3S)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphoric acid	Generator
Presqualene diphosphoric acid	Generator
[(1R,2R,3R)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphate	HMDB
[(1R,2R,3R)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphoric acid	HMDB
(1alpha,2beta(e),3beta(1E,5E))-Diphosphoric acid mono((2-(4,8-dimethyl-3,7-nonadienyl)-2-methyl-3-(2,6,10-trimethyl-1,5,9-undecatrienyl)cyclopropyl)methyl) ester	HMDB
Presqualene pyrophosphate	HMDB
Presqualene diphosphate	HMDB

Chemical Formula

C₃₀H₅₂O₇P₂

Average Molecular Weight

586.68

Monoisotopic Molecular Weight

586.3188

IUPAC Name

[({[(1S,2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional Name

presqualene diphosphate

CAS Registry Number

29849-75-0

SMILES

[H][C@]1(COP(O)(=O)OP(O)(O)=O)[C@]([H])(\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@]1(C)CC\C=C(/C)CCC=C(C)C

InChI Identifier

InChI=1S/C30H52O7P2/c1-23(2)13-9-15-25(5)17-11-18-27(7)21-28-29(22-36-39(34,35)37-38(31,32)33)30(28,8)20-12-19-26(6)16-10-14-24(3)4/h13-14,17,19,21,28-29H,9-12,15-16,18,20,22H2,1-8H3,(H,34,35)(H2,31,32,33)/b25-17+,26-19+,27-21+/t28-,29-,30-/m0/s1

InChI Key

ATZKAUGGNMSCCY-VYCBRMPGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

triterpenyl phosphate (CHEBI:15442 )
triterpenoid (CHEBI:15442 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Subcellular:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	5.31	ALOGPS
logP	8	ChemAxon
logS	-5.7	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	18	ChemAxon
Refractivity	165.33 m³·mol⁻¹	ChemAxon
Polarizability	66.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Presqualene diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gia-4200490000-9a3a83875f6f2ef2cddb	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0200690000-b880904a199b28acdc23	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2352900000-82d62bcceb1656998b10	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-3366920000-574a4a9be60ca4c8d765	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0500090000-557817e75ec0eed28672	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9800020000-6bca51e71e8dd4501523	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-0fe8c0f845a21c70b30c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0100090000-5247a3c4a85015b072da	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-2200090000-09d9e50734c089804e41	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-7dab7bce5c804b18ac2b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0232590000-730292814c7f9261de9b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-3402890000-7a23c1768de1e2a2244f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9317500000-d5d421cf835631935344	2021-09-23	View Spectrum