VD3

(1S,3Z)-3-[(2E)-2-[(1R,3AR,7AS)-7A-METHYL-1-[(2R)-6-METHYLHEPTAN-2-YL]-2,3,3A,5,6,7-HEXAHYDRO-1H-INDEN-4-YLIDENE]ETHYLI DENE]-4-METHYLIDENE-CYCLOHEXAN-1-OL

Created: 2006-06-15
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count72
Chiral Atom Count5
Bond Count74
Aromatic Bond Count0
2D diagram of VD3
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Chemical Component Summary

Name(1S,3Z)-3-[(2E)-2-[(1R,3AR,7AS)-7A-METHYL-1-[(2R)-6-METHYLHEPTAN-2-YL]-2,3,3A,5,6,7-HEXAHYDRO-1H-INDEN-4-YLIDENE]ETHYLI DENE]-4-METHYLIDENE-CYCLOHEXAN-1-OL
SynonymsVITAMIN D3
Systematic Name (OpenEye OEToolkits)(1S)-3-[2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-ol
FormulaC27 H44 O
Molecular Weight384.638
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04OC3CC(=C/C=C1\CCCC2(C)C(C(C)CCCC(C)C)CCC12)\C(=C)CC3
SMILESCACTVS3.341CC(C)CCC[CH](C)[CH]1CC[CH]2C(CCC[C]12C)=CC=C3C[CH](O)CCC3=C
SMILESOpenEye OEToolkits1.5.0CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
Canonical SMILESCACTVS3.341 CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C(/CCC[C@]12C)=C\C=C3/C[C@@H](O)CCC3=C
Canonical SMILESOpenEye OEToolkits1.5.0 CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CCCC2=CC=C3C[C@H](CCC3=C)O)C
InChIInChI1.03 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
InChIKeyInChI1.03 QYSXJUFSXHHAJI-RWDMXNMGSA-N

Drug Info: DrugBank

DrugBank IDDB00169 
NameCholecalciferol
Groups
  • nutraceutical
  • approved
DescriptionVitamin D, in general, is a secosteroid generated in the skin when 7-dehydrocholesterol located there interacts with ultraviolet irradiation - like that commonly found in sunlight [L5689]. Both the endogenous form of vitamin D (that results from 7-dehydrocholesterol transformation), vitamin D3 (cholecalciferol), and the plant-derived form, vitamin D2 (ergocalciferol), are considered the main forms of vitamin d and are found in various types of food for daily intake [L5689]. Structurally, ergocalciferol differs from cholecalciferol in that it possesses a double bond between C22 and C23 and has an additional methyl group at C24 [L5689]. Finally, ergocalciferol is pharmacologically less potent than cholecalciferol, which makes vitamin D3 the preferred agent for medical use [L5689]. Appropriate levels of vitamin D must be upheld in the body in order to maintain calcium and phosphorus levels in a healthy physiologic range to sustain a variety of metabolic functions, transcription regulation, and bone metabolism [A223, L5689, L1782, L5771, F4027, F4042, F4048]. However, studies are also ongoing to determine whether or not cholecalciferol may also play certain roles in cancer, autoimmune disorders, cardiovascular disease, and other medical conditions that may be associated with vitamin D deficiency [L5689].
Synonyms
  • (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol
  • Vitamin D-3
  • Calciol
  • Oleovitamin D3
  • Cholecalciferolum
Brand Names
  • PreGen DHA
  • WesNate DHA
  • Port A Mins Super Calcium 750 With Vitamin D3
  • Provida DHA
  • Duet DHA Balanced
IndicationCholecalciferol use is indicated for the treatment of specific medical conditions like refractory rickets (or vitamin D resistant rickets), hypoparathyroidism, and familial hypophosphatemia [F4027, F4042]. Concurrently, as one of the most commonly utilized forms of vitamin D, cholecalciferol is also very frequently used as a supplement in individuals to maintain sufficient vitamin d levels in the body or to treat vitamin D deficiency, as well as various medical conditions that can be associated directly or indirectly with vitamin d insufficiency like osteoporosis and chronic kidney disease, among others [A176041, A176044, F4051].
Categories
  • Alimentary Tract and Metabolism
  • Bone Density Conservation Agents
  • Calcium-Regulating Hormones and Agents
  • Cholecalciferol, antagonists & inhibitors
  • Cholestanes
ATC-Code
  • M05BB09
  • M05BX53
  • M05BB07
  • M05BB08
  • A11CC55
CAS number67-97-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Vitamin D3 receptorMEAMAASTSLPDPGDFDRNVPRICGVCGDRATGFHFNAMTCEGCKGFFRR...unknownagonist
Vitamin D 25-hydroxylaseMWKLWRAEEGAAALGGALFLLLFALGVRQLLKQRRPMGFPPGPPGLPFIG...unknownsubstrate
Sterol 26-hydroxylase, mitochondrialMAALGCARLRWALRGAGRGLCPHGARAKAAIPAALPSDKATGAPGAGPGV...unknownsubstrate
Cytochrome P450 2J2MLAAMGSLAAALWAVVHPRTLLLGTVAFLLAADFLKRRRPKNYPPGPWRL...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 6221