D2V

(3S,5Z,7E,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-ol

Created: 2008-04-30
Last modified:  2020-05-27

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Chemical Details

Formal Charge0
Atom Count73
Chiral Atom Count6
Bond Count75
Aromatic Bond Count0
2D diagram of D2V

Chemical Component Summary

Name(3S,5Z,7E,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-ol
SynonymsVitamin D2; Ergocalciferol; Deltalin
Systematic Name (OpenEye OEToolkits)(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-ol
FormulaC28 H44 O
Molecular Weight396.648
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04OC3CC(=C/C=C1\CCCC2(C)C(C(/C=C/C(C)C(C)C)C)CCC12)/C(=C)CC3
SMILESCACTVS3.341CC(C)[CH](C)C=C[CH](C)[CH]1CC[CH]2C(CCC[C]12C)=CC=C3C[CH](O)CCC3=C
SMILESOpenEye OEToolkits1.5.0CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
Canonical SMILESCACTVS3.341 CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C
Canonical SMILESOpenEye OEToolkits1.5.0 CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C
InChIInChI1.03 InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
InChIKeyInChI1.03 MECHNRXZTMCUDQ-RKHKHRCZSA-N

Drug Info: DrugBank

DrugBank IDDB00153 
NameErgocalciferol
Groups
  • nutraceutical
  • approved
DescriptionErgocalciferol is an inactivated vitamin D analog.[A177526] It is synthesized by some plants in the presence of UVB light.[T577] The production of ergocalciferol was prompted by the identification of dietary deficiency, more specifically vitamin D, as the main causative factor for the development of rickets. Ergocalciferol was isolated for the first time from yeast in 1931 and its structure was elucidated in 1932.[T580] Ergocalciferol is considered the first vitamin D analog and is differentiated from [cholecalciferol] by the presence of a double bond between C22 and C23 and the presence of a methyl group at C24. These modifications reduce the affinity of ergocalciferol for the vitamin D binding protein resulting in faster clearance, limits its activation, and alters its catabolism.[A177637] The first approved product containing ergocalciferol under the FDA records was developed by US Pharm Holdings and was FDA approved in 1941.[L6058]
Synonyms
  • (3β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
  • Vitamin D2
  • (5Z,7E,22E)-(3S)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol
  • Ergocalciferolum
  • Ergocalciferol
Brand Names
  • Zoo Chews
  • Calcium and Magnesium Citrate With Vitamin D
  • Multiple Vitamins With Iron
  • Radiostol Cap 50000iu
  • Vitamin D 400 I.U. Tablets
IndicationErgocalciferol is indicated for the treatment of hypoparathyroidism, refractory rickets, and familial hypophosphatemia.[FDA label] Hypoparathyroidism is the result of inadequate parathyroid hormone production that occurs due to the presence of damage or removal of the parathyroid glands. This condition produces decreased calcium and increased phosphorus levels.[L6082] Rickets is a condition produced due to a deficiency in vitamin D, calcium or phosphorus. However, this condition can also be related to renal diseases. It is characterized to present weak or soft bones.[A177664] Familial hypophosphatemia is characterized by the impaired transport of phosphate and an altered vitamin D metabolism in the kidneys. The presence of this condition can derive in the presence of osteomalacia, bone softening and rickets.[L6085]
Categories
  • Alimentary Tract and Metabolism
  • Bone Density Conservation Agents
  • Calcium-Regulating Hormones and Agents
  • Diet, Food, and Nutrition
  • Food
ATC-CodeA11CC01
CAS number50-14-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Vitamin D3 receptorMEAMAASTSLPDPGDFDRNVPRICGVCGDRATGFHFNAMTCEGCKGFFRR...unknownagonist
Voltage-dependent calcium channelMSQTKMLKVRVTLFCILAGIVLAMTAVVTDHWAVLSPHMEHHNTTCEAAH...unknowninducer
Ribulose-phosphate 3-epimeraseMASGCKIGPSILNSDLANLGAECLRMLDSGADYLHLDVMDGHFVPNITFG...unknownsubstrate
Cholesterol side-chain cleavage enzyme, mitochondrialMLAKGLPPRSVLVKGCQTFLSAPREGLGRLRVPTGEGAGISTRSPRPFNE...unknownsubstrate
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrialMSSPISKSRSLAAFLQQLRSPRQPPRLVTSTAYTSPQPREVPVCPLTAGG...unknownsubstrate
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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
Pharos CHEMBL1536
PubChem 5280793
ChEMBL CHEMBL1536
ChEBI CHEBI:28934
COD 7118657, 7118658