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(2R)-2-[(1R)-1-hydroxy-1-[(8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,15,16,17-octahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-4-(hydroxymethyl)-5-methyl-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 af9a45ae-834c-44db-aad8-f765e1a9037c
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1R)-1-hydroxy-1-[(8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,15,16,17-octahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-4-(hydroxymethyl)-5-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(CC(OC1=O)C(C)(C2CCC3(C2(CCC4C3CC=C5C4(C(=O)CC=C5)C)C)O)O)CO
SMILES (Isomeric) CC1=C(C[C@@H](OC1=O)[C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)CC=C5)C)C)O)O)CO
InChI InChI=1S/C28H38O6/c1-16-17(15-29)14-23(34-24(16)31)27(4,32)21-11-13-28(33)20-9-8-18-6-5-7-22(30)26(18,3)19(20)10-12-25(21,28)2/h5-6,8,19-21,23,29,32-33H,7,9-15H2,1-4H3/t19-,20+,21-,23+,25+,26-,27+,28+/m0/s1
InChI Key CMYBEXMBTPRVQX-HZRISEJCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H38O6
Molecular Weight 470.60 g/mol
Exact Mass 470.26683893 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 3.40
H-Bond Acceptor 6
H-Bond Donor 3
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-hydroxy-1-[(8R,9S,10R,13R,14R,17S)-14-hydroxy-10,13-dimethyl-1-oxo-7,8,9,11,12,15,16,17-octahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-4-(hydroxymethyl)-5-methyl-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 + 0.9659 96.59%
Caco-2 - 0.6280 62.80%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.8579 85.79%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8610 86.10%
OATP1B3 inhibitior + 0.9434 94.34%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior + 0.6912 69.12%
BSEP inhibitior + 0.9065 90.65%
P-glycoprotein inhibitior + 0.6931 69.31%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7154 71.54%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9168 91.68%
CYP3A4 inhibition - 0.6049 60.49%
CYP2C9 inhibition - 0.9286 92.86%
CYP2C19 inhibition - 0.9465 94.65%
CYP2D6 inhibition - 0.9482 94.82%
CYP1A2 inhibition - 0.8842 88.42%
CYP2C8 inhibition + 0.5304 53.04%
CYP inhibitory promiscuity - 0.9298 92.98%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6138 61.38%
Eye corrosion - 0.9929 99.29%
Eye irritation - 0.9684 96.84%
Skin irritation + 0.6938 69.38%
Skin corrosion - 0.9428 94.28%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6546 65.46%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.5839 58.39%
skin sensitisation - 0.9265 92.65%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.6207 62.07%
Acute Oral Toxicity (c) III 0.6047 60.47%
Estrogen receptor binding + 0.8873 88.73%
Androgen receptor binding + 0.7498 74.98%
Thyroid receptor binding + 0.6476 64.76%
Glucocorticoid receptor binding + 0.8573 85.73%
Aromatase binding + 0.7779 77.79%
PPAR gamma + 0.6456 64.56%
Honey bee toxicity - 0.8475 84.75%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9682 96.82%

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 98.14% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.50% 91.11%
CHEMBL3192 Q9BY41 Histone deacetylase 8 92.04% 93.99%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.43% 95.56%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 89.24% 82.69%
CHEMBL2581 P07339 Cathepsin D 89.08% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.92% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.02% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 87.19% 94.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.16% 85.14%
CHEMBL2996 Q05655 Protein kinase C delta 86.40% 97.79%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.34% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.16% 97.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.47% 99.23%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.71% 93.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.28% 96.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.24% 92.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.20% 94.00%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 83.35% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.09% 93.04%
CHEMBL218 P21554 Cannabinoid CB1 receptor 81.02% 96.61%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.52% 95.89%

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.
Ajuga parviflora

Cross-Links

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PubChem 21668783
LOTUS LTS0039018
wikiData Q104965371