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(2R)-2-[(2R)-2-[(3S,5R,9R,10R,13R,14R,17R)-3-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]propyl]-4-methyl-2H-furan-5-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 4fdc6518-530c-49f3-86ad-53e540cd6311
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-2-[(2R)-2-[(3S,5R,9R,10R,13R,14R,17R)-3-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]propyl]-4-methyl-2H-furan-5-one
SMILES (Canonical) CC1=CC(OC1=O)CC(C)C2CCC3C2(CCC4C3=CCC5C4(CCC(C5(C)C)O)C)C
SMILES (Isomeric) CC1=C[C@H](OC1=O)C[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4C3=CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C
InChI InChI=1S/C29H44O3/c1-17(15-19-16-18(2)26(31)32-19)21-8-9-22-20-7-10-24-27(3,4)25(30)12-14-29(24,6)23(20)11-13-28(21,22)5/h7,16-17,19,21-25,30H,8-15H2,1-6H3/t17-,19-,21-,22+,23+,24+,25+,28-,29-/m1/s1
InChI Key UCIRXCPITKWQAA-KRABGMSBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H44O3
Molecular Weight 440.70 g/mol
Exact Mass 440.32904526 g/mol
Topological Polar Surface Area (TPSA) 46.50 Ų
XlogP 6.90
Atomic LogP (AlogP) 6.46
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[(2R)-2-[(3S,5R,9R,10R,13R,14R,17R)-3-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]propyl]-4-methyl-2H-furan-5-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9972 99.72%
Caco-2 - 0.6098 60.98%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.7919 79.19%
OATP2B1 inhibitior - 0.7192 71.92%
OATP1B1 inhibitior + 0.8678 86.78%
OATP1B3 inhibitior + 0.9533 95.33%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior + 0.5250 52.50%
BSEP inhibitior + 0.8360 83.60%
P-glycoprotein inhibitior + 0.5720 57.20%
P-glycoprotein substrate - 0.7103 71.03%
CYP3A4 substrate + 0.6677 66.77%
CYP2C9 substrate - 0.8032 80.32%
CYP2D6 substrate - 0.8757 87.57%
CYP3A4 inhibition + 0.5203 52.03%
CYP2C9 inhibition - 0.8458 84.58%
CYP2C19 inhibition - 0.7394 73.94%
CYP2D6 inhibition - 0.9414 94.14%
CYP1A2 inhibition - 0.8489 84.89%
CYP2C8 inhibition - 0.7758 77.58%
CYP inhibitory promiscuity - 0.7622 76.22%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5841 58.41%
Eye corrosion - 0.9935 99.35%
Eye irritation - 0.9544 95.44%
Skin irritation + 0.6112 61.12%
Skin corrosion - 0.9321 93.21%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7403 74.03%
Micronuclear - 0.8300 83.00%
Hepatotoxicity - 0.5698 56.98%
skin sensitisation - 0.6658 66.58%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity - 0.6514 65.14%
Acute Oral Toxicity (c) III 0.6550 65.50%
Estrogen receptor binding + 0.7434 74.34%
Androgen receptor binding + 0.5578 55.78%
Thyroid receptor binding + 0.7008 70.08%
Glucocorticoid receptor binding + 0.8706 87.06%
Aromatase binding + 0.6371 63.71%
PPAR gamma + 0.6195 61.95%
Honey bee toxicity - 0.8107 81.07%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9932 99.32%

Targets

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Proven Targets:

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

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL221 P23219 Cyclooxygenase-1 94.17% 90.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.24% 97.25%
CHEMBL1937 Q92769 Histone deacetylase 2 92.92% 94.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.43% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.16% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.11% 91.11%
CHEMBL2581 P07339 Cathepsin D 89.96% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.92% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.81% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.73% 95.89%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.28% 82.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.00% 94.45%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 85.31% 96.38%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.89% 93.56%
CHEMBL3192 Q9BY41 Histone deacetylase 8 84.69% 93.99%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 84.26% 93.03%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.15% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.77% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.32% 99.23%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.57% 90.08%
CHEMBL3401 O75469 Pregnane X receptor 81.48% 94.73%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 81.00% 85.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.37% 86.33%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.20% 90.71%

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.
Abies firma

Cross-Links

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PubChem 162885487
LOTUS LTS0011499
wikiData Q105269932