Bovine Metabolome Database: Showing metabocard for 20a,22b-Dihydroxycholesterol (BMDB0006763)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:25:43 UTC

Update Date

2020-04-22 15:18:30 UTC

BMDB ID

BMDB0006763

Secondary Accession Numbers

BMDB06763

Metabolite Identification

Common Name

20a,22b-Dihydroxycholesterol

Description

20a,22b-Dihydroxycholesterol belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. 20a,22b-Dihydroxycholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 20a,22b-Dihydroxycholesterol participates in a number of enzymatic reactions, within cattle. In particular, 20a,22b-Dihydroxycholesterol can be converted into pregnenolone and 4-methylpentanal through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 20a,22b-Dihydroxycholesterol can be biosynthesized from 22b-hydroxycholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In cattle, 20a,22b-dihydroxycholesterol is involved in the metabolic pathway called the steroidogenesis pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
20alpha,22beta-Dihydroxycholesterol	HMDB

Chemical Formula

C₂₇H₄₆O₃

Average Molecular Weight

418.6523

Monoisotopic Molecular Weight

418.344695338

IUPAC Name

(2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol

Traditional Name

(2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol

CAS Registry Number

15234-55-6

SMILES

[H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C

InChI Identifier

InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19?,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1

InChI Key

ISBSSBGEYIBVTO-IVMOZYHGSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Trihydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
Hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm

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	5.08	ALOGPS
logP	4.72	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.66 m³·mol⁻¹	ChemAxon
Polarizability	51.5 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4259400000-35c8f139c691d00dfc8e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00xr-2111139000-a480b3deb74eef32e383	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-1014900000-d02629f92bcfa0d4d5bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-8098400000-ec5061b658871254b471	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9065000000-9198f9a283da1d4a6a06	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0003900000-7cd68582455580a1aeeb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-2397500000-8b9915c82bf3ecb52681	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-7289100000-1e37d62442300af9ead1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-f2cb6399034352e924c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0023900000-85cd6f9f87eb3b745726	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05o1-4139500000-f72eacbae8e6876f643a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0021900000-e2e06cd0437b86637824	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-4596100000-bb184f1626e9252f10ec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-5930000000-979f3659179997a1c795	View in MoNA