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withalongolide I

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 6da3f8eb-cbfa-4a69-8ba3-1bc769b90d6d
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
IUPAC Name (2R)-5-(hydroxymethyl)-2-[(1S)-1-[(3R,8S,9S,10R,13S,14S,17R)-10-(hydroxymethyl)-13-methyl-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4-methyl-2,3-dihydropyran-6-one
SMILES (Canonical) CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC=C5C4(C(=O)CC(C5)OC6C(C(C(C(O6)CO)O)O)O)CO)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]3CC=C5[C@@]4(C(=O)C[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)CO)C)CO
InChI InChI=1S/C34H50O11/c1-16-10-25(44-31(42)21(16)13-35)17(2)22-6-7-23-20-5-4-18-11-19(43-32-30(41)29(40)28(39)26(14-36)45-32)12-27(38)34(18,15-37)24(20)8-9-33(22,23)3/h4,17,19-20,22-26,28-30,32,35-37,39-41H,5-15H2,1-3H3/t17-,19+,20-,22+,23-,24-,25+,26+,28+,29-,30+,32+,33+,34-/m0/s1
InChI Key PRNFAKRMKREHJM-XYLPFXPVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C34H50O11
Molecular Weight 634.80 g/mol
Exact Mass 634.33531241 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.16
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 7

Synonyms

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CHEBI:69113
CHEMBL1934461
Q27137454
3-O-beta-D-glucopyranosyl-19,27-dihydroxy-1-oxo-witha-5,24-dienolide
(3beta,22R)-19,27-dihydroxy-1,26-dioxo-22,26-epoxyergosta-5,24-dien-3-yl beta-D-glucopyranoside

2D Structure

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2D Structure of withalongolide I

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7135 71.35%
Caco-2 - 0.8668 86.68%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.8629 86.29%
OATP2B1 inhibitior - 0.5772 57.72%
OATP1B1 inhibitior + 0.8503 85.03%
OATP1B3 inhibitior + 0.7884 78.84%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.5298 52.98%
BSEP inhibitior - 0.5293 52.93%
P-glycoprotein inhibitior + 0.6820 68.20%
P-glycoprotein substrate + 0.5274 52.74%
CYP3A4 substrate + 0.7508 75.08%
CYP2C9 substrate - 0.8025 80.25%
CYP2D6 substrate - 0.9003 90.03%
CYP3A4 inhibition - 0.9295 92.95%
CYP2C9 inhibition - 0.9215 92.15%
CYP2C19 inhibition - 0.9385 93.85%
CYP2D6 inhibition - 0.9550 95.50%
CYP1A2 inhibition - 0.8971 89.71%
CYP2C8 inhibition + 0.6336 63.36%
CYP inhibitory promiscuity - 0.9438 94.38%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6009 60.09%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9332 93.32%
Skin irritation + 0.4910 49.10%
Skin corrosion - 0.9419 94.19%
Ames mutagenesis - 0.7324 73.24%
Human Ether-a-go-go-Related Gene inhibition + 0.7016 70.16%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.5908 59.08%
skin sensitisation - 0.9349 93.49%
Respiratory toxicity + 0.8444 84.44%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity - 0.5850 58.50%
Acute Oral Toxicity (c) III 0.5730 57.30%
Estrogen receptor binding + 0.7759 77.59%
Androgen receptor binding + 0.7659 76.59%
Thyroid receptor binding - 0.6631 66.31%
Glucocorticoid receptor binding + 0.6051 60.51%
Aromatase binding + 0.6712 67.12%
PPAR gamma + 0.5967 59.67%
Honey bee toxicity - 0.6861 68.61%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5350 53.50%
Fish aquatic toxicity + 0.9668 96.68%

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
CHEMBL1937 Q92769 Histone deacetylase 2 96.27% 94.75%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.67% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.18% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.95% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.83% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.63% 95.56%
CHEMBL5103 Q969S8 Histone deacetylase 10 91.25% 90.08%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.06% 96.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.90% 94.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.96% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.01% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.65% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.70% 100.00%
CHEMBL226 P30542 Adenosine A1 receptor 85.13% 95.93%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.61% 93.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.69% 93.04%
CHEMBL3401 O75469 Pregnane X receptor 83.42% 94.73%
CHEMBL5028 O14672 ADAM10 82.26% 97.50%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.40% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.91% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.86% 95.89%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.50% 96.21%
CHEMBL4581 P52732 Kinesin-like protein 1 80.17% 93.18%

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

Cross-Links

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PubChem 56926205
LOTUS LTS0124819
wikiData Q27137454