PlantaeDB Logo
Login Sign-up

(1R,2R,4R,5R,10R,11S,14R,15S,16S)-4,5-dihydroxy-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.01,14.02,11.05,10]nonadecan-9-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 5b25d1a7-e80a-48d2-ae22-267658eee8ef
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (1R,2R,4R,5R,10R,11S,14R,15S,16S)-4,5-dihydroxy-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.01,14.02,11.05,10]nonadecan-9-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C2(C3CCC4(C3(CCC5C4CC(C6(C5(C(=O)CCC6)C)O)O)C)O2)C)CO
SMILES (Isomeric) CC1=C(C(=O)O[C@H](C1)[C@@]2([C@H]3CC[C@@]4([C@@]3(CC[C@H]5[C@H]4C[C@H]([C@@]6([C@@]5(C(=O)CCC6)C)O)O)C)O2)C)CO
InChI InChI=1S/C28H40O7/c1-15-12-22(34-23(32)16(15)14-29)26(4)19-8-11-28(35-26)18-13-21(31)27(33)9-5-6-20(30)25(27,3)17(18)7-10-24(19,28)2/h17-19,21-22,29,31,33H,5-14H2,1-4H3/t17-,18+,19-,21+,22+,24+,25-,26-,27-,28+/m0/s1
InChI Key YWJMSSUOWWLAFE-KCVKPQPBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C28H40O7
Molecular Weight 488.60 g/mol
Exact Mass 488.27740361 g/mol
Topological Polar Surface Area (TPSA) 113.00 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.84
H-Bond Acceptor 7
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (1R,2R,4R,5R,10R,11S,14R,15S,16S)-4,5-dihydroxy-16-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.01,14.02,11.05,10]nonadecan-9-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9378 93.78%
Caco-2 - 0.6591 65.91%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.8558 85.58%
OATP2B1 inhibitior - 0.7053 70.53%
OATP1B1 inhibitior + 0.8241 82.41%
OATP1B3 inhibitior + 0.9463 94.63%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.9243 92.43%
P-glycoprotein inhibitior - 0.5502 55.02%
P-glycoprotein substrate - 0.5617 56.17%
CYP3A4 substrate + 0.7029 70.29%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8974 89.74%
CYP3A4 inhibition - 0.6892 68.92%
CYP2C9 inhibition - 0.9161 91.61%
CYP2C19 inhibition - 0.9427 94.27%
CYP2D6 inhibition - 0.9590 95.90%
CYP1A2 inhibition - 0.9238 92.38%
CYP2C8 inhibition + 0.5338 53.38%
CYP inhibitory promiscuity - 0.9635 96.35%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Danger 0.4564 45.64%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9446 94.46%
Skin irritation + 0.6544 65.44%
Skin corrosion - 0.9361 93.61%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5099 50.99%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.6624 66.24%
skin sensitisation - 0.9229 92.29%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.5849 58.49%
Acute Oral Toxicity (c) I 0.8349 83.49%
Estrogen receptor binding + 0.7992 79.92%
Androgen receptor binding + 0.7694 76.94%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.8017 80.17%
Aromatase binding + 0.7881 78.81%
PPAR gamma + 0.6300 63.00%
Honey bee toxicity - 0.8202 82.02%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9722 97.22%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.23% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.17% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.51% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.28% 91.11%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 91.52% 82.69%
CHEMBL3192 Q9BY41 Histone deacetylase 8 90.82% 93.99%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.19% 99.23%
CHEMBL2581 P07339 Cathepsin D 89.48% 98.95%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 88.62% 93.03%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.16% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 87.46% 94.75%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 87.14% 93.04%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.66% 86.33%
CHEMBL2996 Q05655 Protein kinase C delta 86.15% 97.79%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 85.45% 96.09%
CHEMBL5103 Q969S8 Histone deacetylase 10 84.54% 90.08%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.09% 92.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.75% 94.00%
CHEMBL5028 O14672 ADAM10 80.30% 97.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.25% 95.50%

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.
Withania coagulans

Cross-Links

Top
PubChem 100920595
LOTUS LTS0230312
wikiData Q105366789