5,6-trans-Vitamin D3

Details

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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

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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

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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
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 5,6-trans-Vitamin D3

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Solanum glaucophyllum

Cross-Links

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PubChem 5283711
LOTUS LTS0252962
wikiData Q105230494