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Withaferine A

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 19cf4ed7-6355-4d24-9803-9a197d7fce86
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name 6-hydroxy-15-[1-[5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)CO
SMILES (Isomeric) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)CO
InChI InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3
InChI Key DBRXOUCRJQVYJQ-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H38O6
Molecular Weight 470.60 g/mol
Exact Mass 470.26683893 g/mol
Topological Polar Surface Area (TPSA) 96.40 Ų
XlogP 3.80
Atomic LogP (AlogP) 3.35
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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NSC-101088
CHEMBL2143369
CHEBI:95348
DBRXOUCRJQVYJQ-UHFFFAOYSA-N
BCP31971
LSM-6721
FT-0675861
Q27167229
NSC 101088; NSC-101088; NSC101088; NSC 273757; NSC-273757; NSC273757
4-Hydroxy-9-(1-[5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl)-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one #
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Withaferine A

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8983 89.83%
Caco-2 - 0.6673 66.73%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.7714 77.14%
OATP2B1 inhibitior - 0.7144 71.44%
OATP1B1 inhibitior + 0.8216 82.16%
OATP1B3 inhibitior + 0.9702 97.02%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5771 57.71%
BSEP inhibitior + 0.9059 90.59%
P-glycoprotein inhibitior + 0.6132 61.32%
P-glycoprotein substrate + 0.5948 59.48%
CYP3A4 substrate + 0.7332 73.32%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8921 89.21%
CYP3A4 inhibition - 0.8547 85.47%
CYP2C9 inhibition - 0.8867 88.67%
CYP2C19 inhibition - 0.9390 93.90%
CYP2D6 inhibition - 0.9517 95.17%
CYP1A2 inhibition - 0.7829 78.29%
CYP2C8 inhibition + 0.4609 46.09%
CYP inhibitory promiscuity - 0.9338 93.38%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5377 53.77%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9627 96.27%
Skin irritation + 0.5455 54.55%
Skin corrosion - 0.9323 93.23%
Ames mutagenesis - 0.5102 51.02%
Human Ether-a-go-go-Related Gene inhibition + 0.6673 66.73%
Micronuclear - 0.7100 71.00%
Hepatotoxicity + 0.5655 56.55%
skin sensitisation - 0.8846 88.46%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.4850 48.50%
Acute Oral Toxicity (c) I 0.5780 57.80%
Estrogen receptor binding + 0.7526 75.26%
Androgen receptor binding + 0.7750 77.50%
Thyroid receptor binding + 0.5884 58.84%
Glucocorticoid receptor binding + 0.8317 83.17%
Aromatase binding + 0.7180 71.80%
PPAR gamma + 0.5737 57.37%
Honey bee toxicity - 0.7451 74.51%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9671 96.71%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL5514 P42858 Huntingtin 316.2 nM
 Potency
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL2581 P07339 Cathepsin D 95.38% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.26% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.70% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.11% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.05% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.35% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 86.95% 97.79%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.27% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.97% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.34% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.87% 82.69%
CHEMBL5103 Q969S8 Histone deacetylase 10 84.53% 90.08%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.90% 99.23%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.67% 93.04%
CHEMBL1871 P10275 Androgen Receptor 81.52% 96.43%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.91% 86.33%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.44% 93.56%
CHEMBL5028 O14672 ADAM10 80.35% 97.50%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.23% 90.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.11% 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.
Physalis longifolia
Vassobia breviflora
Withania coagulans
Withania somnifera

Cross-Links

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PubChem 580064
LOTUS LTS0228735
wikiData Q27167229