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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
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ChemBase ID:
155996
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Molecular Formular:
C27H44O3
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Molecular Mass:
416.63646
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Monoisotopic Mass:
416.32904527
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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
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Cite this record
CBID:155996 http://www.chembase.cn/molecule-155996.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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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
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IUPAC Traditional name
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(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
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Synonyms
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(24R)-,24,25-Dihydroxycholecalciferol
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Secalciferol
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(24R)-24,25-Dihydroxyvitamin D3
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CAS Number
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MDL Number
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Beilstein Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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13.849643
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H Acceptors
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3
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H Donor
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3
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LogD (pH = 5.5)
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4.5794425
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LogD (pH = 7.4)
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4.5794425
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Log P
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4.5794425
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Molar Refractivity
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126.4221 cm3
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Polarizability
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49.421616 Å3
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Polar Surface Area
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60.69 Å2
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Rotatable Bonds
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6
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
Sigma Aldrich
Sigma Aldrich -
17943
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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. |
PATENTS
PATENTS
PubChem Patent
Google Patent