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(2S)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4-methyl-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID d6e70f69-af9c-4158-935b-f8764509fcf9
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2S)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4-methyl-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(CO)C2CCC3C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)C)COC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) CC1=C(C(=O)O[C@@H](C1)[C@@H](CO)[C@H]2CC[C@@H]3[C@]2(CC[C@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=CC5)C)O)O)C)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C34H50O12/c1-16-11-23(45-30(42)19(16)15-44-31-29(41)28(40)27(39)24(14-36)46-31)18(13-35)21-7-6-20-17-12-26(38)34(43)9-4-5-25(37)33(34,3)22(17)8-10-32(20,21)2/h4-5,17-18,20-24,26-29,31,35-36,38-41,43H,6-15H2,1-3H3/t17-,18-,20-,21+,22-,23-,24+,26+,27+,28-,29+,31+,32+,33-,34-/m0/s1
InChI Key MIHRHFBCKBVQMG-UOWGMIHQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H50O12
Molecular Weight 650.80 g/mol
Exact Mass 650.33022703 g/mol
Topological Polar Surface Area (TPSA) 203.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 0.13
H-Bond Acceptor 12
H-Bond Donor 7
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13R,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethyl]-4-methyl-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6790 67.90%
Caco-2 - 0.8741 87.41%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.8033 80.33%
OATP2B1 inhibitior - 0.8609 86.09%
OATP1B1 inhibitior + 0.8439 84.39%
OATP1B3 inhibitior + 0.8903 89.03%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5798 57.98%
BSEP inhibitior + 0.9106 91.06%
P-glycoprotein inhibitior + 0.6745 67.45%
P-glycoprotein substrate + 0.5959 59.59%
CYP3A4 substrate + 0.7484 74.84%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9011 90.11%
CYP3A4 inhibition - 0.8984 89.84%
CYP2C9 inhibition - 0.9204 92.04%
CYP2C19 inhibition - 0.9387 93.87%
CYP2D6 inhibition - 0.9545 95.45%
CYP1A2 inhibition - 0.9218 92.18%
CYP2C8 inhibition + 0.6721 67.21%
CYP inhibitory promiscuity - 0.9671 96.71%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6448 64.48%
Eye corrosion - 0.9914 99.14%
Eye irritation - 0.9290 92.90%
Skin irritation + 0.5261 52.61%
Skin corrosion - 0.9451 94.51%
Ames mutagenesis - 0.6522 65.22%
Human Ether-a-go-go-Related Gene inhibition + 0.7460 74.60%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.7163 71.63%
skin sensitisation - 0.9328 93.28%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.6097 60.97%
Acute Oral Toxicity (c) I 0.5806 58.06%
Estrogen receptor binding + 0.7893 78.93%
Androgen receptor binding + 0.7828 78.28%
Thyroid receptor binding - 0.6242 62.42%
Glucocorticoid receptor binding + 0.6461 64.61%
Aromatase binding + 0.6446 64.46%
PPAR gamma + 0.6012 60.12%
Honey bee toxicity - 0.6523 65.23%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.9442 94.42%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.32% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.08% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.87% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.58% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.41% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.38% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.28% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.07% 95.89%
CHEMBL2996 Q05655 Protein kinase C delta 88.93% 97.79%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.51% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.02% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.61% 97.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.73% 97.25%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 86.06% 96.95%
CHEMBL226 P30542 Adenosine A1 receptor 85.48% 95.93%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.19% 94.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.95% 93.04%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.04% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.97% 99.23%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.50% 96.21%
CHEMBL204 P00734 Thrombin 82.24% 96.01%
CHEMBL1871 P10275 Androgen Receptor 81.37% 96.43%

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.
Datura metel

Cross-Links

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PubChem 163043634
LOTUS LTS0212025
wikiData Q105164778