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(2R)-5-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-[(5R,6R,8S,9R,10R,12R,13S,14S,17R)-5,6,12-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 39defd4a-bdfb-4871-a9df-fcf01be1143f
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2R)-5-(hydroxymethyl)-2-[(1R)-2-hydroxy-1-[(5R,6R,8S,9R,10R,12R,13S,14S,17R)-5,6,12-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(CO)C2CCC3C2(C(CC4C3CC(C5(C4(C(=O)C=CC5)C)O)O)O)C)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@H](CO)[C@H]2CC[C@@H]3[C@@]2([C@@H](C[C@@H]4[C@H]3C[C@H]([C@@]5([C@@]4(C(=O)C=CC5)C)O)O)O)C)CO
InChI InChI=1S/C28H40O8/c1-14-9-21(36-25(34)16(14)12-29)17(13-30)19-7-6-18-15-10-24(33)28(35)8-4-5-22(31)27(28,3)20(15)11-23(32)26(18,19)2/h4-5,15,17-21,23-24,29-30,32-33,35H,6-13H2,1-3H3/t15-,17-,18-,19+,20+,21+,23+,24+,26-,27-,28-/m0/s1
InChI Key IIGAMLZDLFOICW-GZSFFWHGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H40O8
Molecular Weight 504.60 g/mol
Exact Mass 504.27231823 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 1.40
Atomic LogP (AlogP) 1.28
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)-2-[(1R)-2-hydroxy-1-[(5R,6R,8S,9R,10R,12R,13S,14S,17R)-5,6,12-trihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-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 + 0.8684 86.84%
Caco-2 - 0.7693 76.93%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.8158 81.58%
OATP2B1 inhibitior - 0.5754 57.54%
OATP1B1 inhibitior + 0.8841 88.41%
OATP1B3 inhibitior + 0.9220 92.20%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5614 56.14%
BSEP inhibitior + 0.9471 94.71%
P-glycoprotein inhibitior - 0.5088 50.88%
P-glycoprotein substrate + 0.6574 65.74%
CYP3A4 substrate + 0.7028 70.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9074 90.74%
CYP3A4 inhibition - 0.7859 78.59%
CYP2C9 inhibition - 0.9289 92.89%
CYP2C19 inhibition - 0.9135 91.35%
CYP2D6 inhibition - 0.9583 95.83%
CYP1A2 inhibition - 0.8671 86.71%
CYP2C8 inhibition + 0.5518 55.18%
CYP inhibitory promiscuity - 0.9776 97.76%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6231 62.31%
Eye corrosion - 0.9925 99.25%
Eye irritation - 0.9566 95.66%
Skin irritation + 0.5949 59.49%
Skin corrosion - 0.9447 94.47%
Ames mutagenesis - 0.5211 52.11%
Human Ether-a-go-go-Related Gene inhibition + 0.6451 64.51%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.5421 54.21%
skin sensitisation - 0.9244 92.44%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.5446 54.46%
Acute Oral Toxicity (c) III 0.4405 44.05%
Estrogen receptor binding + 0.8120 81.20%
Androgen receptor binding + 0.7659 76.59%
Thyroid receptor binding + 0.5352 53.52%
Glucocorticoid receptor binding + 0.7604 76.04%
Aromatase binding + 0.6617 66.17%
PPAR gamma + 0.5178 51.78%
Honey bee toxicity - 0.7438 74.38%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9555 95.55%

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 94.47% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.28% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.13% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.74% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.11% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.56% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.57% 100.00%
CHEMBL226 P30542 Adenosine A1 receptor 88.64% 95.93%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 87.04% 93.04%
CHEMBL2996 Q05655 Protein kinase C delta 86.42% 97.79%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.28% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.83% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.22% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.57% 86.33%
CHEMBL5103 Q969S8 Histone deacetylase 10 82.09% 90.08%
CHEMBL1871 P10275 Androgen Receptor 81.91% 96.43%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 80.27% 96.37%

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.
Datura innoxia

Cross-Links

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PubChem 162955146
LOTUS LTS0034741
wikiData Q105113447