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(2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(3S,4S,5R,6R,8S,9S,10R,13S,14S,17R)-3,4,5,6-tetrahydroxy-10,13-dimethyl-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 7cafb09a-7312-44e3-8aa2-df44251e6058
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-[(3S,4S,5R,6R,8S,9S,10R,13S,14S,17R)-3,4,5,6-tetrahydroxy-10,13-dimethyl-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)CC(C5O)O)C)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)C[C@@H]([C@@H]5O)O)C)O)O)C)CO
InChI InChI=1S/C28H42O8/c1-13-9-21(36-25(34)16(13)12-29)14(2)17-5-6-18-15-10-23(32)28(35)24(33)20(30)11-22(31)27(28,4)19(15)7-8-26(17,18)3/h14-15,17-21,23-24,29-30,32-33,35H,5-12H2,1-4H3/t14-,15-,17+,18-,19-,20-,21+,23+,24-,26+,27-,28+/m0/s1
InChI Key MRLVVVMKNONDOH-YGDYIFIGSA-N
Popularity 1 reference 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 1.90
Atomic LogP (AlogP) 1.50
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 3

Synonyms

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orb2893475
CHEMBL2047420
TN8551
(R)-3-(Hydroxymethyl)-4-methyl-6-((S)-1-((3S,4S,5R,6R,8S,9S,10R,13S,14S,17R)-3,4,5,6-tetrahydroxy-10,13-dimethyl-1-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl)-5,6-dihydro-2H-pyran-2-one

2D Structure

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2D Structure of (2R)-5-(hydroxymethyl)-4-methyl-2-[(1S)-1-[(3S,4S,5R,6R,8S,9S,10R,13S,14S,17R)-3,4,5,6-tetrahydroxy-10,13-dimethyl-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 + 0.8209 82.09%
Caco-2 - 0.7816 78.16%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7829 78.29%
OATP2B1 inhibitior - 0.5629 56.29%
OATP1B1 inhibitior + 0.8462 84.62%
OATP1B3 inhibitior + 0.9163 91.63%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5688 56.88%
BSEP inhibitior + 0.7803 78.03%
P-glycoprotein inhibitior - 0.5544 55.44%
P-glycoprotein substrate + 0.5671 56.71%
CYP3A4 substrate + 0.7329 73.29%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9056 90.56%
CYP3A4 inhibition - 0.8216 82.16%
CYP2C9 inhibition - 0.9199 91.99%
CYP2C19 inhibition - 0.9302 93.02%
CYP2D6 inhibition - 0.9568 95.68%
CYP1A2 inhibition - 0.8942 89.42%
CYP2C8 inhibition - 0.5934 59.34%
CYP inhibitory promiscuity - 0.9672 96.72%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6907 69.07%
Eye corrosion - 0.9925 99.25%
Eye irritation - 0.9471 94.71%
Skin irritation + 0.6327 63.27%
Skin corrosion - 0.9421 94.21%
Ames mutagenesis - 0.6232 62.32%
Human Ether-a-go-go-Related Gene inhibition + 0.6666 66.66%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.6030 60.30%
skin sensitisation - 0.9270 92.70%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.4907 49.07%
Acute Oral Toxicity (c) III 0.4997 49.97%
Estrogen receptor binding + 0.6591 65.91%
Androgen receptor binding + 0.7829 78.29%
Thyroid receptor binding - 0.5265 52.65%
Glucocorticoid receptor binding + 0.6420 64.20%
Aromatase binding + 0.6742 67.42%
PPAR gamma + 0.5758 57.58%
Honey bee toxicity - 0.8014 80.14%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9567 95.67%

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
CHEMBL2581 P07339 Cathepsin D 93.52% 98.95%
CHEMBL204 P00734 Thrombin 93.52% 96.01%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.42% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.46% 95.56%
CHEMBL2996 Q05655 Protein kinase C delta 92.03% 97.79%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.76% 97.09%
CHEMBL1937 Q92769 Histone deacetylase 2 90.16% 94.75%
CHEMBL299 P17252 Protein kinase C alpha 89.66% 98.03%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.78% 99.23%
CHEMBL5103 Q969S8 Histone deacetylase 10 88.60% 90.08%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.66% 96.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.57% 82.69%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 87.23% 93.04%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.46% 100.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 85.79% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.98% 85.14%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.81% 93.03%
CHEMBL226 P30542 Adenosine A1 receptor 82.08% 95.93%
CHEMBL325 Q13547 Histone deacetylase 1 81.80% 95.92%
CHEMBL3192 Q9BY41 Histone deacetylase 8 81.40% 93.99%
CHEMBL5028 O14672 ADAM10 81.09% 97.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.37% 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.
Withania aristata

Cross-Links

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PubChem 66572353
LOTUS LTS0218745
wikiData Q105170677