PlantaeDB Logo
Login Sign-up

(2S)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[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

Top
Internal ID b2b8ce2d-4180-42d7-a9f3-814828ee4e31
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2S)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC(C5(C4(C(=O)C=CC5)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=CC5)C)O)O)C)CO
InChI InChI=1S/C28H40O6/c1-15-12-22(34-25(32)18(15)14-29)16(2)19-7-8-20-17-13-24(31)28(33)10-5-6-23(30)27(28,4)21(17)9-11-26(19,20)3/h5-6,16-17,19-22,24,29,31,33H,7-14H2,1-4H3/t16-,17+,19-,20+,21+,22+,24-,26-,27+,28+/m1/s1
InChI Key LDWRZKAVHDHGID-SBVKEWLXSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C28H40O6
Molecular Weight 472.60 g/mol
Exact Mass 472.28248899 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 3.90
Atomic LogP (AlogP) 3.34
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (2S)-2-[(1R)-1-[(5R,6R,8S,9S,10R,13S,14S,17R)-5,6-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9102 91.02%
Caco-2 - 0.6422 64.22%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.8225 82.25%
OATP2B1 inhibitior - 0.7134 71.34%
OATP1B1 inhibitior + 0.8576 85.76%
OATP1B3 inhibitior + 0.9236 92.36%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5688 56.88%
BSEP inhibitior + 0.9657 96.57%
P-glycoprotein inhibitior + 0.5774 57.74%
P-glycoprotein substrate + 0.6207 62.07%
CYP3A4 substrate + 0.7269 72.69%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9074 90.74%
CYP3A4 inhibition - 0.7105 71.05%
CYP2C9 inhibition - 0.9203 92.03%
CYP2C19 inhibition - 0.9261 92.61%
CYP2D6 inhibition - 0.9609 96.09%
CYP1A2 inhibition - 0.8420 84.20%
CYP2C8 inhibition + 0.4497 44.97%
CYP inhibitory promiscuity - 0.9720 97.20%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6419 64.19%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.9659 96.59%
Skin irritation + 0.6729 67.29%
Skin corrosion - 0.9432 94.32%
Ames mutagenesis - 0.6092 60.92%
Human Ether-a-go-go-Related Gene inhibition + 0.6595 65.95%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.5617 56.17%
skin sensitisation - 0.9260 92.60%
Respiratory toxicity + 0.8889 88.89%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.5882 58.82%
Acute Oral Toxicity (c) III 0.4395 43.95%
Estrogen receptor binding + 0.8027 80.27%
Androgen receptor binding + 0.7949 79.49%
Thyroid receptor binding + 0.6315 63.15%
Glucocorticoid receptor binding + 0.8061 80.61%
Aromatase binding + 0.6942 69.42%
PPAR gamma + 0.5869 58.69%
Honey bee toxicity - 0.7781 77.81%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9645 96.45%

Targets

Top

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 94.32% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.32% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.09% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 93.70% 97.79%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.93% 100.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.91% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.78% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.70% 96.09%
CHEMBL5103 Q969S8 Histone deacetylase 10 86.74% 90.08%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.20% 97.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.49% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.80% 93.04%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.38% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 83.82% 94.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.74% 86.33%
CHEMBL1871 P10275 Androgen Receptor 83.58% 96.43%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.04% 95.89%
CHEMBL3310 Q96DB2 Histone deacetylase 11 82.97% 88.56%
CHEMBL226 P30542 Adenosine A1 receptor 82.46% 95.93%
CHEMBL221 P23219 Cyclooxygenase-1 82.26% 90.17%
CHEMBL299 P17252 Protein kinase C alpha 81.38% 98.03%

Plants that contains it

Top
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 integrifolia

Cross-Links

Top
PubChem 162970267
LOTUS LTS0033662
wikiData Q105150417