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(2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(4S,5S,6R,8S,9S,10S,13S,14S,17R)-4,5,6-trihydroxy-10-(hydroxymethyl)-13-methyl-1-oxo-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 ca734883-f2e0-45f9-9236-198dc1b3b68e
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(4S,5S,6R,8S,9S,10S,13S,14S,17R)-4,5,6-trihydroxy-10-(hydroxymethyl)-13-methyl-1-oxo-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC(C5(C4(C(=O)CCC5O)CO)O)O)C)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)CC[C@@H]5O)CO)O)O)C)CO
InChI InChI=1S/C28H42O8/c1-14-10-21(36-25(34)17(14)12-29)15(2)18-4-5-19-16-11-24(33)28(35)23(32)7-6-22(31)27(28,13-30)20(16)8-9-26(18,19)3/h15-16,18-21,23-24,29-30,32-33,35H,4-13H2,1-3H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28-/m0/s1
InChI Key DFSBDOXCQOJIAK-KVQZJPFPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H42O8
Molecular Weight 506.60 g/mol
Exact Mass 506.28796829 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.50
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(4S,5S,6R,8S,9S,10S,13S,14S,17R)-4,5,6-trihydroxy-10-(hydroxymethyl)-13-methyl-1-oxo-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 + 0.7519 75.19%
Caco-2 - 0.7897 78.97%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7760 77.60%
OATP2B1 inhibitior - 0.5630 56.30%
OATP1B1 inhibitior + 0.8674 86.74%
OATP1B3 inhibitior + 0.9142 91.42%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5614 56.14%
BSEP inhibitior + 0.7803 78.03%
P-glycoprotein inhibitior - 0.5549 55.49%
P-glycoprotein substrate + 0.5091 50.91%
CYP3A4 substrate + 0.7309 73.09%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9056 90.56%
CYP3A4 inhibition - 0.8800 88.00%
CYP2C9 inhibition - 0.9283 92.83%
CYP2C19 inhibition - 0.9188 91.88%
CYP2D6 inhibition - 0.9546 95.46%
CYP1A2 inhibition - 0.9056 90.56%
CYP2C8 inhibition + 0.4512 45.12%
CYP inhibitory promiscuity - 0.9742 97.42%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6726 67.26%
Eye corrosion - 0.9919 99.19%
Eye irritation - 0.9588 95.88%
Skin irritation + 0.5567 55.67%
Skin corrosion - 0.9434 94.34%
Ames mutagenesis - 0.6532 65.32%
Human Ether-a-go-go-Related Gene inhibition - 0.3693 36.93%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.5283 52.83%
skin sensitisation - 0.9252 92.52%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.6674 66.74%
Acute Oral Toxicity (c) III 0.4967 49.67%
Estrogen receptor binding + 0.7190 71.90%
Androgen receptor binding + 0.8016 80.16%
Thyroid receptor binding - 0.5901 59.01%
Glucocorticoid receptor binding + 0.6661 66.61%
Aromatase binding + 0.7179 71.79%
PPAR gamma + 0.5219 52.19%
Honey bee toxicity - 0.7862 78.62%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9459 94.59%

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
CHEMBL299 P17252 Protein kinase C alpha 93.93% 98.03%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.68% 97.25%
CHEMBL2581 P07339 Cathepsin D 92.77% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 91.88% 97.79%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.74% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.55% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.26% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.35% 100.00%
CHEMBL5103 Q969S8 Histone deacetylase 10 88.70% 90.08%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 88.11% 93.04%
CHEMBL1937 Q92769 Histone deacetylase 2 87.63% 94.75%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.45% 82.69%
CHEMBL204 P00734 Thrombin 87.10% 96.01%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 86.63% 96.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 85.84% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.12% 96.09%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.79% 95.89%
CHEMBL3192 Q9BY41 Histone deacetylase 8 82.21% 93.99%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.91% 86.33%
CHEMBL3310 Q96DB2 Histone deacetylase 11 81.57% 88.56%
CHEMBL5028 O14672 ADAM10 80.65% 97.50%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.03% 98.75%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.02% 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.
Jaborosa leucotricha

Cross-Links

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PubChem 101712449
LOTUS LTS0178826
wikiData Q104978264