Ergocalciferol

Details

• Internal ID: 4c646f26-df0b-4446-8c6e-1c22feaed3bd
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Vitamin D and derivatives
• IUPAC Name: (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-methylidenecyclohexan-1-ol
• SMILES (Canonical): CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• SMILES (Isomeric): C[C@H](/C=C/[C@H](C)C(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/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
• InChI Key: MECHNRXZTMCUDQ-RKHKHRCZSA-N
• Popularity: 6,416 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₄O
• Molecular Weight: 396.60 g/mol
• Exact Mass: 396.339216023 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 7.40
• Atomic LogP (AlogP): 7.64
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• VITAMIN D2
• Calciferol
• Viosterol
• 50-14-6
• Ergorone
• Deltalin
• Ercalciol
• Drisdol
• Ostelin
• Oleovitamin D2
• Detalup
• Sterogyl
• Condocaps
• Crystallina
• Fortodyl
• Mulsiferol
• Radsterin
• Condol
• Deratol
• Diactol
• Ertron
• Geltabs
• Daral
• Divit urto
• Novovitamin-D
• D-Tracetten
• Hi-Deratol
• Calciferon 2
• Dee-Ronal
• Vitavel-D
• D-Arthin
• Dee-Ron
• Vio-D
• Rodine C
• Calciferolum
• Hyperkil
• Rodinec
• Ergocalciferolum
• Mina D2
• Radiostol
• VitaminD2
• Mykostin
• Davitin
• Decaps
• Infron
• Metadee
• Shock-ferol
• Davitamon D
• Dee-Osterol
• Ergocalciferolo
• Dee-Roual
• Disdrol
• Haliver
• Buco-D
• (+)-Vitamin D2
• Geltabs Vitamin D
• Irradiated ergosterol
• Sorex C.R.
• Oleovitamin D
• HSDB 819
• Ergocalciferolo [DCIT]
• CHEBI:28934
• C28H44O
• Oleovitamin D, Synthetic
• Uvesterol D
• Vitamin d (ergocalciferol)
• Vitamina D2
• EINECS 200-014-9
• Irradiated ergosta-5,7,22-trien-3-beta-ol
• UNII-VS041H42XC
• Ergocalciferols
• NSC 62792
• Condacaps
• Crtron
• Ergocalciferolum [INN-Latin]
• VS041H42XC
• 9,10-Secoergosta-5,7,10(19),22-tetraen-3-beta-ol
• Synthetic Vitamin D
• NSC-62792
• Doral [Vitamin Derivative]
• Vitamin D2 (Ergocalciferol)
• (5Z,7E,22E)-(3S)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol
• Radstein
• Viostdrol
• ERGOCALCIFEROL, (+)-
• Uvesterol-D
• DTXSID5020233
• 9,10-Seco(5Z,7E,22E)-5,7,10(19),22-ergostatetraen-3-ol
• vitamin d-2
• (3-beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10,(19),22-tetraen-3-ol
• (3beta,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
• (5Z,7E,22E)-(3S)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
• Ergocalciferol [USP:INN:BAN:JAN]
• Ergosterol irradiated
• Shock-ferol sterogyl
• MFCD00166988
• (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-methylidenecyclohexan-1-ol
• Ergosterol, irradiated
• 9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol, (3b,5Z,7E,22E)-
• 9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol, (3.beta.,5Z,7E,22E)-
• 9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol, (3beta,5Z,7E,22E)-
• Doral (Vitamin Derivative)
• ERGOCALCIFEROL (MART.)
• ERGOCALCIFEROL [MART.]
• ERGOCALCIFEROL (USP-RS)
• Ergocalciferol [INN:BAN:JAN]
• ERGOCALCIFEROL [USP-RS]
• Calciferol (TN)
• Drisdol (TN)
• ERGOCALCIFEROL (EP IMPURITY)
• ERGOCALCIFEROL [EP IMPURITY]
• Sorex C.R
• (3S,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
• ERGOCALCIFEROL (EP MONOGRAPH)
• ERGOCALCIFEROL [EP MONOGRAPH]
• ERGOCALCIFEROL (USP MONOGRAPH)
• ERGOCALCIFEROL [USP MONOGRAPH]
• SMR000857106
• Vitamin D 2
• (3S,5Z,7E,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-ol
• DTXCID70233
• Ergocalciferol; (Vitamin D2)
• Ergocalciferol [BAN:INN:JAN]
• Osteil
• delta-Tracetten
• Lanes
• NSC62792
• delta-Arthin
• beta-ol
• C28-H44-O
• vitaminum d2
• D-forte
• Eciferol D2
• Ergoral D2
• Sterogyl-15
• Sterogyl 15H
• Cyclohexanol, 4-methylene-3-((2E)-2-((1R,3aS,7aR)-octahydro-7a-methyl-1-((1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl)-4H-inden-4-ylidene)ethylidene)-, (1S,3Z)-
• Cyclohexanol, 4-methylene-3-[(2E)-2-[(1R,3aS,7aR)-octahydro-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-4H-inden-4-ylidene]ethylidene]-, (1S,3Z)-
• Prestwick_554
• Vio D
• Ergo-D2
• Osto-D2
• Prestwick3_000420
• bmse000510
• VITAMIN D2 [MI]
• 7E677DC1-E1C4-4FC5-8F4A-BCE1857F7E87
• VITAMIN D2 [FCC]
• SCHEMBL3420
• CHEMBL1536
• ERGOCALCIFEROL [INN]
• ERGOCALCIFEROL [JAN]
• ergocalciferol; 50-14-6
• BSPBio_000380
• Ergocalciferol (JP17/USP)
• ERGOCALCIFEROL [HSDB]
• ERGOCALCIFEROL [INCI]
• MLS001332467
• MLS001332468
• ERGOCALCIFEROL [VANDF]
• VITAMIN D2 [WHO-IP]
• BPBio1_000418
• MEGxm0_000466
• ERGOCALCIFEROL [WHO-DD]
• ERGOCALCIFEROL [WHO-IP]
• (3-beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol
• ACon1_002187
• A11CC01
• (3S,5Z,7E,14xi,17alpha,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-ol
• MECHNRXZTMCUDQ-RKHKHRCZSA-N
• HMS2096C22
• HMS2230E20
• Ciclohexanol, 4-metilen-3-[(2E)-2-[(1R, 3aS, 7aR)-octahidro-7a-metil-1-[(1R, 2E, 4R)-1,4,5-trimetil-2-hexen-1-il]-4H-inden-4-ilideno] etilideno]-, (1S, 3Z)-
• CS-M1019
• ERGOCALCIFEROL [ORANGE BOOK]
• BDBM50247883
• LMST03010001
• s4035
• Vitamin D2; Ergocalciferol; Deltalin
• AKOS022185284
• CCG-268614
• DB00153
• ERGOCALCIFEROLUM [WHO-IP LATIN]
• LS-3228
• Ergocalciferol, Sigma Reference Standard
• NCGC00166307-02
• NCGC00166307-03
• AS-11649
• BP-31119
• Ergocalciferol (D2), analytical standard
• HY-76542
• Irradiated ergosta-5,7,22-trien-3beta-ol
• Vitamin D2 Ergocalciferol 400,000 IU/g
• Ergocalciferol, 40,000,000 USP units/g
• C05441
• D00187
• EN300-21690916
• Q139200
• Q-201930
• 9,10-Secoergosta-5,7,10(19),22-tetraen-3b-ol
• Ergocalciferol, >=98.0% (sum of enantiomers, HPLC)
• 22-tetraen 3beta 9,10,Secoergosta-5,7,10(19)-ol
• (5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-ol
• 9,10,SECOERGOSTA-5,7,10(19),22-TETRAEN 3-BETA-OL
• Ergocalciferol, British Pharmacopoeia (BP) Reference Standard
• Ergocalciferol, European Pharmacopoeia (EP) Reference Standard
• Ergocalciferol, United States Pharmacopeia (USP) Reference Standard
• 24-METHYL-9,10-SECOCHOLESTA-5,7,10(19),22-TETRAENE-3beta-OL
• (3.BETA.,5Z,7E,22E)-9,10-SECOERGOSTA-5,7,10(19),22-TETRAEN-3-OL
• 24-METHYL-9,10-SECOCHOLESTA-5,7,10( 19),22-TETRAENE-3.BETA.-OL [WHO-IP]
• 9,10-SECOERGOSTA-5,7,10(19),22-TETRAEN-3-OL,(3-BETA,5Z,7E,22E)-
• Ergocalciferol (Vitamin D2), Pharmaceutical Secondary Standard; Certified Reference Material
• Ergocalciferol for system suitability, EuropePharmacopoeia (EP) Reference Standard
• (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(E,1R,4R)-1,4,5-trimethylhex-2-enyl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol
• (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• 4-methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3aH)-indanylidene]ethylidene]-Cyclohexanol
• Cycloheanol, 4-methylene-3-(2-(tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3aH)-indanylidene)ethylidene)-
• CYCLOHEXANOL, 4-METHYLENE-3-(2-(TETRAHYDRO-7A-METHYL-1-(1,4,5-TRIMETHYL-2-HEXENYL)-4(3AH)-INDANYLIDENE)ETHYLIDENE)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5790	57.90%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5154	51.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7432	74.32%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7111	71.11%
P-glycoprotein inhibitior	+	0.5962	59.62%
P-glycoprotein substrate	-	0.7463	74.63%
CYP3A4 substrate	+	0.5798	57.98%
CYP2C9 substrate	-	0.8255	82.55%
CYP2D6 substrate	-	0.7567	75.67%
CYP3A4 inhibition	-	0.8142	81.42%
CYP2C9 inhibition	-	0.8924	89.24%
CYP2C19 inhibition	-	0.8784	87.84%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.6229	62.29%
CYP inhibitory promiscuity	-	0.8163	81.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5685	56.85%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9756	97.56%
Skin irritation	+	0.6463	64.63%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6616	66.16%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	+	0.6827	68.27%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	I	0.8502	85.02%
Estrogen receptor binding	+	0.8436	84.36%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.6717	67.17%
Glucocorticoid receptor binding	+	0.6219	62.19%
Aromatase binding	-	0.6081	60.81%
PPAR gamma	+	0.6206	62.06%
Honey bee toxicity	-	0.8019	80.19%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9929	99.29%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	1.1 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	31.6 nM; 100 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1977	P11473	Vitamin D receptor	99.33%	99.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.73%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.06%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	94.24%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	92.81%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.24%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.89%	93.56%
CHEMBL237	P41145	Kappa opioid receptor	90.65%	98.10%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.45%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.22%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.30%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.24%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.18%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.86%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.40%	94.45%
CHEMBL5203	P33316	dUTP pyrophosphatase	85.93%	99.18%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.52%	91.07%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	83.18%	88.81%
CHEMBL4072	P07858	Cathepsin B	83.08%	93.67%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.80%	100.00%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.64%	95.00%
CHEMBL1902	P62942	FK506-binding protein 1A	80.15%	97.05%

Plants that contains it

• Humulus lupulus
• Medicago sativa

Cross-Links

• PubChem: 5280793
• NPASS: NPC9161
• ChEMBL: CHEMBL1536
• LOTUS: LTS0064053
• wikiData: Q139200