5,6-trans-Vitamin D3

Details

• Internal ID: f1626b77-e957-4ca1-adcc-9307cc8c5b21
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Vitamin D and derivatives
• IUPAC Name: (1S,3E)-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-FVUVGDFOSA-N
• Popularity: 9 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
• Atomic LogP (AlogP): 7.62
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• trans-Vitamin D3
• 5,6-trans-Vitamin D3
• (1S,3E)-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
• cholecalciferol EP impurity A
• (5E,7E)-(3S)-9,10-seco-5,7,10(19)-cholestatrien-3-ol
• (5E)-vitamin D3 / (5E)-cholecalciferol / (5E)-calciol
• (1S,3E)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• 5,6-trans-Cholecalciferol
• DTXCID306294
• CAS-67-97-0
• NCGC00159331-02
• (5E)-calciol
• (5e)-cholecalciferol
• (3S,5E,7E)-9,10-secocholesta-5,7,10-trien-3-ol
• (5E)-vitamin D3
• CHOLECALCIFEROL IMPURITY A [EP IMPURITY]
• Cholecalciferol, (5E)-
• SCHEMBL3127
• W28SLM7V6D
• CHEMBL1236645
• CHEBI:145213
• DTXSID901316617
• Tox21_111578
• Tox21_202546
• HY-15398A
• LMST03020220
• AKOS026750034
• NCGC00159331-07
• NCGC00159331-15
• NCGC00179565-01
• NCGC00179565-02
• NCGC00260095-01
• AS-82639
• CS-0111447
• E85758
• EN300-22979549
• (E,E)-9,10-secocholesta-5,7,10(19)-trien-3beta-ol
• 9,10-Secocholesta-5,7,10(19)-trien-3beta-ol, (E,E)-
• (3beta,5E,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
• 9,10-Secocholesta-5,7,10(19)-trien-3-ol, (3beta,5E,7E)-
• (1S,3E)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-Dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylenecyclohexanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7333	73.33%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Lysosomes	0.5091	50.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8594	85.94%
OATP1B3 inhibitior	-	0.3549	35.49%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7208	72.08%
P-glycoprotein inhibitior	-	0.5565	55.65%
P-glycoprotein substrate	-	0.5686	56.86%
CYP3A4 substrate	+	0.5176	51.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7337	73.37%
CYP3A4 inhibition	-	0.7881	78.81%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9551	95.51%
CYP1A2 inhibition	-	0.9256	92.56%
CYP2C8 inhibition	-	0.6961	69.61%
CYP inhibitory promiscuity	-	0.7093	70.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6318	63.18%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9613	96.13%
Skin irritation	+	0.5585	55.85%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7771	77.71%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	+	0.6904	69.04%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.9113	91.13%
Acute Oral Toxicity (c)	I	0.8559	85.59%
Estrogen receptor binding	+	0.8316	83.16%
Androgen receptor binding	+	0.8658	86.58%
Thyroid receptor binding	+	0.6827	68.27%
Glucocorticoid receptor binding	+	0.6724	67.24%
Aromatase binding	-	0.4861	48.61%
PPAR gamma	+	0.5810	58.10%
Honey bee toxicity	-	0.8736	87.36%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	400 nM	EC50	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	63.1 nM	Potency	via Super-PRED
CHEMBL1977	P11473	Vitamin D receptor	0.21 nM	EC50	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

• Solanum glaucophyllum

Cross-Links

• PubChem: 5283711
• LOTUS: LTS0252962
• wikiData: Q105230494