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(2R)-2-[(1R)-1-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-2,3,4,7,8,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-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 59bea7d1-74ec-4d2a-af3d-496ec1623b4c
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(1R)-1-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-2,3,4,7,8,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2(CCC3(C2(CCC4C3CC=C5C4(C(=O)CCC5)C)C)O)O)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@]2(CC[C@@]3([C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(C(=O)CCC5)C)C)O)O)CO
InChI InChI=1S/C28H40O6/c1-16-14-22(34-24(31)19(16)15-29)17(2)27(32)12-13-28(33)21-9-8-18-6-5-7-23(30)26(18,4)20(21)10-11-25(27,28)3/h8,17,20-22,29,32-33H,5-7,9-15H2,1-4H3/t17-,20+,21-,22-,25-,26+,27+,28-/m1/s1
InChI Key WBHXRFICUBWLCX-LWWNUPBASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H40O6
Molecular Weight 472.60 g/mol
Exact Mass 472.28248899 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 3.62
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-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-2,3,4,7,8,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-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 + 0.9468 94.68%
Caco-2 - 0.6273 62.73%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.8044 80.44%
OATP2B1 inhibitior - 0.5729 57.29%
OATP1B1 inhibitior + 0.8679 86.79%
OATP1B3 inhibitior + 0.9291 92.91%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior + 0.5845 58.45%
BSEP inhibitior + 0.8542 85.42%
P-glycoprotein inhibitior - 0.4849 48.49%
P-glycoprotein substrate - 0.5278 52.78%
CYP3A4 substrate + 0.6846 68.46%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9148 91.48%
CYP3A4 inhibition - 0.6686 66.86%
CYP2C9 inhibition - 0.9338 93.38%
CYP2C19 inhibition - 0.9554 95.54%
CYP2D6 inhibition - 0.9589 95.89%
CYP1A2 inhibition - 0.8588 85.88%
CYP2C8 inhibition + 0.5286 52.86%
CYP inhibitory promiscuity - 0.9260 92.60%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6476 64.76%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.9542 95.42%
Skin irritation + 0.6323 63.23%
Skin corrosion - 0.9405 94.05%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6673 66.73%
Micronuclear - 0.8200 82.00%
Hepatotoxicity + 0.6178 61.78%
skin sensitisation - 0.9224 92.24%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.5640 56.40%
Acute Oral Toxicity (c) III 0.6440 64.40%
Estrogen receptor binding + 0.8083 80.83%
Androgen receptor binding + 0.7517 75.17%
Thyroid receptor binding + 0.5505 55.05%
Glucocorticoid receptor binding + 0.7829 78.29%
Aromatase binding + 0.7345 73.45%
PPAR gamma + 0.5655 56.55%
Honey bee toxicity - 0.8304 83.04%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9675 96.75%

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 98.23% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.47% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.44% 99.23%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.28% 91.11%
CHEMBL1937 Q92769 Histone deacetylase 2 92.22% 94.75%
CHEMBL2581 P07339 Cathepsin D 91.28% 98.95%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 90.49% 93.04%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 90.35% 96.38%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.32% 96.09%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.31% 93.99%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.19% 97.09%
CHEMBL5103 Q969S8 Histone deacetylase 10 87.96% 90.08%
CHEMBL3359 P21462 Formyl peptide receptor 1 87.83% 93.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.57% 86.33%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.85% 82.69%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 85.85% 93.03%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.38% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.37% 95.89%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.36% 90.71%
CHEMBL4040 P28482 MAP kinase ERK2 81.94% 83.82%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.62% 94.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.58% 92.62%
CHEMBL3310 Q96DB2 Histone deacetylase 11 80.46% 88.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.37% 97.14%

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 162959998
LOTUS LTS0154749
wikiData Q105300768