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55721-11-4 molecular structure
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(3R,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol

ChemBase ID: 155996
Molecular Formular: C27H44O3
Molecular Mass: 416.63646
Monoisotopic Mass: 416.32904527
SMILES and InChIs

SMILES:
C[C@H](CC[C@H](C(C)(C)O)O)[C@H]1CC[C@@H]2[C@@]1(CCC/C/2=C\C=C\1/C[C@H](CCC1=C)O)C
Canonical SMILES:
O[C@H]1CCC(=C)/C(=C/C=C/2\CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CC[C@H](C(O)(C)C)O)C)C)/C1
InChI:
InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/t19-,22+,23-,24+,25-,27-/m1/s1
InChIKey:
FCKJYANJHNLEEP-SUUCIXNTSA-N

Cite this record

CBID:155996 http://www.chembase.cn/molecule-155996.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3R,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
IUPAC Traditional name
(3R,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
Synonyms
(24R)-,24,25-Dihydroxycholecalciferol
Secalciferol
(24R)-24,25-Dihydroxyvitamin D3
CAS Number
55721-11-4
MDL Number
MFCD00941417
Beilstein Number
4567039
PubChem SID
24850812
162250134
PubChem CID
12895035

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
17943 external link Add to cart Please log in.
Data Source Data ID
PubChem 12895035 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.849643  H Acceptors
H Donor LogD (pH = 5.5) 4.5794425 
LogD (pH = 7.4) 4.5794425  Log P 4.5794425 
Molar Refractivity 126.4221 cm3 Polarizability 49.421616 Å3
Polar Surface Area 60.69 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
RTECS
VS2895000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
28 expand Show data source
Safety Statements
28-36/37-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300 expand Show data source
GHS Precautionary statements
P264-P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥98% (vitamin + pre-vitamin, HPLC) expand Show data source
Empirical Formula (Hill Notation)
C27H44O3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 17943 external link
Biochem/physiol Actions
Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol) is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3. Other analogues of cholecalciferol result from different hydroxylations. 24R,25-Dihydroxyvitamin D3 is a catabolite of 25-Dihydroxyvitamin D3 and a putative regulator of developmental bone formation. 24R,25-Dihydroxyvitamin D3 is a substrate for renal 25-hydroxyvitamin D3 1 α-hydroxylase. 24R,25-Dihydroxyvitamin D3 is an endogenous regulator of apo A-I synthesis through a VDR-independent signaling mechanism and an inhibitor of Pi-induced apoptosis through Ca2+, PLD, and PLC signaling and through LPA-LPA1/3-G(αi)-PI(3)K-mdm2-mediated p53 degradation.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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