Cholecalciferol

Details

• Internal ID: da297be6-c60f-475c-9db2-84a0b4923d61
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Vitamin D and derivatives
• IUPAC Name: (1S,3Z)-3-[(2E)-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-methylidenecyclohexan-1-ol
• SMILES (Canonical): CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• SMILES (Isomeric): C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C
• InChI: 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/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1
• InChI Key: QYSXJUFSXHHAJI-YRZJJWOYSA-N
• Popularity: 63,125 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O
• Molecular Weight: 384.60 g/mol
• Exact Mass: 384.339216023 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 7.90

Synonyms

• cholecalciferol
• 67-97-0
• Colecalciferol
• Calciol
• Ricketon
• Oleovitamin D3
• Deparal
• Arachitol
• Delsterol
• Trivitan
• Ebivit
• Vigorsan
• vitamin d-3
• Colecalcipherol
• Colecalciferolum
• Cholecalciferolum
• D3-Vicotrat
• D3-Vigantol
• (+)-Vitamin D3
• Vi-de-3-hydrosol
• NEO Dohyfral D3
• Provitina
• Quintox
• Rampage
• Vitinc Dan-Dee-3
• 1406-16-2
• Delta-D
• Cholecalciferol, D3
• Colecalciferolo
• Vi-De3
• Duphafral D3 1000
• Colecalciferol D3
• Vitamin D 3
• Irradiated 7-dehydrocholesterol
• CCRIS 6286
• HSDB 820
• Videkhol
• Colecalciferolo [DCIT]
• 7-Dehydrocholesterol, irradiated
• FeraCol
• CHEBI:28940
• C27H44O
• Granuvit D3
• Vitamin d (cholecalciferol)
• CC
• EINECS 200-673-2
• Colecalciferolum [INN-Latin]
• EPA Pesticide Chemical Code 202901
• NSC 375571
• NSC-375571
• UNII-1C6V77QF41
• VIGANTOLETTEN
• CCRIS 5813
• (1S,3Z)-3-[(2E)-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-methylidenecyclohexan-1-ol
• Colecalciferol [INN]
• 9,10-Secocholesta-5,7,10(19)-trien-3-beta-ol
• Vitamin d3 (as cholecalciferol)
• DP-R206
• 1C6V77QF41
• Vitamin d assay system suitability
• Vitamin D3 emulsifiable
• EINECS 215-797-2
• UNII-9VU1KI44GP
• calcirol
• AK R215 COMPONENT COLECALCIFEROL
• AK-R215 COMPONENT COLECALCIFEROL
• Vitamin D3 (Cholecalciferol)
• 9,10-Seco(5Z,7E)-5,7,10(19)-cholestatrien-3-ol
• DTXSID6026294
• (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
• (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol
• 9,10-Secocholesta-5,7,10(19)-trien-3-ol, (3beta,5Z,7E)-
• Cholecalciferol [USAN:BAN:JAN]
• VidDe-3-hydrosol
• Cholecalciferol [USP:BAN:JAN:ISO]
• NSC375571
• DP-R206 COMPONENT VITAMIN D3
• Colecalciferol (INN)
• (3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
• Vitamin D3 10 microg/mL in Acetonitrile
• (5Z,7E)-(3S)-9,10-seco-5,7,10(19)-cholestatrien-3-ol
• 9,10-Secocholestra-5,7,10(19)-trien-3-ol, (3beta,5Z,7E)-
• FOSAMAX PLUS D COMPONENT CHOLECALCIFEROL
• 9,10-Secocholesta-5,7,10(19)-trien-3-ol
• CHOLECALCIFEROL COMPONENT OF FOSAMAX PLUS D
• COLECALCIFEROL (MART.)
• COLECALCIFEROL [MART.]
• Micro-dee
• 9,10-Seco(5Z,7E)-5,7,10(19)-cholestatrien-3beta-ol
• 9,10-Secocholesta-5(Z),7(E),10(19)-trien-3(.beta.)-ol
• 9,10-Secocholesta-5,7,10(19)-trien-3-ol, (3.beta.,5Z,7E)-
• CHOLECALCIFEROL (EP MONOGRAPH)
• CHOLECALCIFEROL [EP MONOGRAPH]
• (5e)-cholecalciferol
• CHOLECALCIFEROL (USP MONOGRAPH)
• CHOLECALCIFEROL [USP MONOGRAPH]
• Delta-D (TN)
• (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-dimethylhexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol
• (S,Z)-3-(2-((1R,3aS,7aR,E)-7a-methyl-1-((R)-6-methylheptan-2-yl)octahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexan-1-ol
• Cyclohexanol, 3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-, (1S,3Z)-
• 22350-41-0
• MFCD00078131
• DTXCID306294
• Vitamin D3; Cholecalciferol
• Devaron
• (3.beta.,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
• vitaminum d3
• Prestwick_63
• Cholecalciferol D3
• NCGC00159331-02
• (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]ETHYLIDENE]-4-METHYLIDENE-CYCLOHEXAN-1-OL
• Cyclohexanol, 3-((2E)-2-((1R,3aS,7aR)-1-((1R)-1,5-dimethylhexyl)octahydro-7a-methyl-4H-inden-4-ylidene)ethylidene)-4-methylene-, (1S,3Z)-
• 9,10-secocholesta-5,7,10-trien-3-ol
• ()-Vitamin D3
• CHOLECALCIFEROL IMPURITY A (EP IMPURITY)
• Prestwick3_000429
• bmse000507
• UPCMLD-DP152
• VITAMIN D3 [MI]
• VITAMIN D3 [FCC]
• SCHEMBL3126
• 9VU1KI44GP
• CHEMBL1042
• BSPBio_000418
• CHOLECALCIFEROL [ISO]
• CHOLECALCIFEROL [JAN]
• 9,10-Secocholesta-5,7,10(19)-trien-3beta-ol
• Cholecalciferol; 67-97-0
• Cholecalciferol (JP17/USP)
• CHOLECALCIFEROL [HSDB]
• CHOLECALCIFEROL [INCI]
• CHOLECALCIFEROL [VANDF]
• BPBio1_000460
• MEGxm0_000458
• COLECALCIFEROL [WHO-DD]
• COLECALCIFEROL [WHO-IP]
• CHOLECALCIFEROL [USP-RS]
• UPCMLD-DP152:001
• ACon1_001997
• Cholecalciferol [USP:BAN:JAN]
• A11CC05
• COLECALCIFEROL [EMA EPAR]
• HMS2096E20
• Cholecalciferol, >=98% (HPLC)
• (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)ETHYLIDENE)-4-METHYLIDENE-CYCLOHEXAN-1-OL
• (3 beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol
• Cholecalciferol, analytical standard
• BDBM50030475
• CHOLECALCIFEROL [ORANGE BOOK]
• LMST03020001
• LS-825
• s4063
• Cholecalciferol for system suitability
• 5,7-CHOLESTADIEN-3-BETAL-OL
• AKOS015950641
• AC-8884
• CCG-268466
• COLECALCIFEROLUM [WHO-IP LATIN]
• CS-1179
• CS-O-01095
• DB00169
• LS-1570
• SMP1_000068
• USEPA/OPP Pesticide Code: 202901
• NCGC00091072-01
• NCGC00159331-04
• BS-42465
• HY-15398
• Cholecalciferol (D3), analytical standard
• C05443
• D00188
• Cholecalciferol, meets USP testing specifications
• 9,10-Secocholesta-5,7,10(19)-trien-3?-ol
• Q139347
• (5E,7E)-9,10-Secocholesta-5,7,10-trien-3-ol
• Q-201931
• VITAMIN D ASSAY SYSTEM SUITABILITY [USP-RS]
• 3-beta,Z,7E-9,10-Secocholestr-5,7,10(19)-trien-3-ol
• (3-beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol
• (3beta,Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol
• 9,10-Secocholesta-5,7,10(19)-trien-3-ol, (3b,5Z,7E)-
• Cholecalciferol, European Pharmacopoeia (EP) Reference Standard
• Colecalciferol, British Pharmacopoeia (BP) Reference Standard
• (5E,7E)-9,10-SECOCHOLESTA-5,7,10(19)-TRIEN-3beta-OL
• Cholecalciferol, United States Pharmacopeia (USP) Reference Standard
• (3 BETA, 5Z, 7E)-9,10-SECOCHOLESTA-5,7,10(19)-TRIEN-3-OL
• Cholecalciferol for system suitability, European Pharmacopoeia (EP) Reference Standard
• (1S,3Z)-3-[(2E)-2-[7a-Methyl-1-(6-methylheptan-2-yl)-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• Cholecalciferol (Vitamin D3), Pharmaceutical Secondary Standard; Certified Reference Material
• Ciclohexanol, 3-[(2e)-2-[(1r, 3as, 7ar)-1-[(1r)-1,5-dimetilhexil] octahidro-7a-metil-4h-inden-4-ilideno] etilideno]-4-metilen-, (1s, 3z)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	22387.2 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	15848.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM	Potency	via CMAUP
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	400 nM; 400 nM	EC50; EC50	PMID: 25790278; via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	25118.9 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	63.1 nM	Potency	via Super-PRED
CHEMBL1977	P11473	Vitamin D receptor	0.21 nM; 0.21 nM	EC50; EC50	PMID: 25305688; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL237	P41145	Kappa opioid receptor	96.47%	98.10%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.74%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.94%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	94.33%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.42%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.23%	95.93%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.97%	93.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.68%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.47%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.35%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.63%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.02%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.58%	82.69%
CHEMBL233	P35372	Mu opioid receptor	83.32%	97.93%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.06%	92.88%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.51%	95.50%
CHEMBL3837	P07711	Cathepsin L	81.34%	96.61%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.56%	92.62%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.48%	98.33%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.42%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.36%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.23%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.19%	93.00%

Plants that contains it

• Cestrum diurnum
• Medicago sativa
• Solanum glaucophyllum
• Solanum melongena
• Theobroma cacao

Cross-Links

• PubChem: 5280795
• NPASS: NPC269877
• ChEMBL: CHEMBL1042
• LOTUS: LTS0243695
• wikiData: Q139347