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(2R)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13R,14S,17S)-5,6-dihydroxy-13-(hydroxymethyl)-10-methyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-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 df21273b-153d-4331-b78e-fe4e7a49118d
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13R,14S,17S)-5,6-dihydroxy-13-(hydroxymethyl)-10-methyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)CO)O)C
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@](C)([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)CO)O)C
InChI InChI=1S/C28H40O7/c1-15-12-23(35-24(32)16(15)2)26(4,33)20-8-7-19-17-13-22(31)28(34)10-5-6-21(30)25(28,3)18(17)9-11-27(19,20)14-29/h5-6,17-20,22-23,29,31,33-34H,7-14H2,1-4H3/t17-,18+,19+,20-,22-,23-,25+,26-,27-,28+/m1/s1
InChI Key GXNOESKMNSBHCJ-OQQHPQTBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H40O7
Molecular Weight 488.60 g/mol
Exact Mass 488.27740361 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 2.45
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13R,14S,17S)-5,6-dihydroxy-13-(hydroxymethyl)-10-methyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-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 + 0.9102 91.02%
Caco-2 - 0.6774 67.74%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8225 82.25%
OATP2B1 inhibitior - 0.8595 85.95%
OATP1B1 inhibitior + 0.8853 88.53%
OATP1B3 inhibitior + 0.9236 92.36%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5688 56.88%
BSEP inhibitior + 0.8411 84.11%
P-glycoprotein inhibitior - 0.4875 48.75%
P-glycoprotein substrate + 0.5723 57.23%
CYP3A4 substrate + 0.7288 72.88%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9074 90.74%
CYP3A4 inhibition - 0.7105 71.05%
CYP2C9 inhibition - 0.9203 92.03%
CYP2C19 inhibition - 0.9261 92.61%
CYP2D6 inhibition - 0.9609 96.09%
CYP1A2 inhibition - 0.8420 84.20%
CYP2C8 inhibition + 0.5793 57.93%
CYP inhibitory promiscuity - 0.9720 97.20%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6419 64.19%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.9604 96.04%
Skin irritation + 0.6729 67.29%
Skin corrosion - 0.9432 94.32%
Ames mutagenesis - 0.6215 62.15%
Human Ether-a-go-go-Related Gene inhibition + 0.7160 71.60%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.5179 51.79%
skin sensitisation - 0.9260 92.60%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.6084 60.84%
Acute Oral Toxicity (c) III 0.4395 43.95%
Estrogen receptor binding + 0.8417 84.17%
Androgen receptor binding + 0.8035 80.35%
Thyroid receptor binding + 0.5767 57.67%
Glucocorticoid receptor binding + 0.7071 70.71%
Aromatase binding + 0.6894 68.94%
PPAR gamma + 0.6129 61.29%
Honey bee toxicity - 0.8150 81.50%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9645 96.45%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.87% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.69% 85.14%
CHEMBL4040 P28482 MAP kinase ERK2 95.20% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.04% 95.56%
CHEMBL2996 Q05655 Protein kinase C delta 93.76% 97.79%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.07% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.66% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.93% 97.14%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.72% 93.04%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.70% 89.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.57% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.67% 86.33%
CHEMBL218 P21554 Cannabinoid CB1 receptor 85.83% 96.61%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.83% 96.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.41% 99.23%
CHEMBL2581 P07339 Cathepsin D 84.08% 98.95%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 80.97% 90.93%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.54% 95.89%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.49% 96.95%

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.
Physalis coztomatl

Cross-Links

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PubChem 11844625
LOTUS LTS0038337
wikiData Q105023226