Showing Compound 5,6-trans-Vitamin D3 (FDB024037)

Record Information

Version

1.0

Creation date

2011-09-21 00:38:52 UTC

Update date

2015-07-21 06:57:58 UTC

Primary ID

FDB024037

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5,6-trans-Vitamin D3

Description

5,6-trans-vitamin D3 is the result of photodegradation of vitamin D3, and once formed in the skin, exposure to sunlight results in its rapid photodegradation to a variety of photoproducts. During chronic exposure to sunlight vitamin D3 in the skin can be photoisomerized to a variety of photoproducts, including 5,6-trans-vitamin D3. Because 5,6-Trans-vitamin D3 is a photoproduct of vitamin D3 and have a pseudo-1-alpha-hydroxyl structure due to the 180-degree rotation of the 3-hydroxyl group during isomerization. 5,6-trans-vitamin D3 can mimic the intestinal calcium transport activity of 1alpha,25(OH)2D (the active form of vitamine D). (PMID: 10876100, 2541158) [HMDB]

CAS Number

22350-41-0

Structure

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

Synonyms

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Synonym	Source
3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-Cyclohexanol	hmdb
5,6-trans-Cholecalciferol	hmdb
5,6-trans-Vitamin D3	hmdb
trans-Vitamin D3	hmdb

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00038 g/L	ALOGPS
logP	7.98	ALOGPS
logP	7.13	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.38	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.22 m³·mol⁻¹	ChemAxon
Polarizability	48.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C27H44O

IUPAC name

(1S)-3-{2-[(1R,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

InChI Identifier

InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/t21-,24+,25-,26?,27-/m1/s1

InChI Key

QYSXJUFSXHHAJI-CJJWQTMXSA-N

Isomeric SMILES

[H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C(CCC[C@]12C)=CC=C1C[C@@]([H])(O)CCC1=C

Average Molecular Weight

384.6377

Monoisotopic Molecular Weight

384.33921603

Classification

Description

Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

12303099

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06719

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 5,6-trans-Vitamin D3 (FDB024037)

Structure for FDB024037 (5,6-trans-Vitamin D3)