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(2S)-4-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2-[2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-(5-oxo-2H-furan-4-yl)ethyl]-2H-furan-5-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 462c7056-34f1-4418-b698-c6fa0160f5df
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name (2S)-4-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2-[2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-(5-oxo-2H-furan-4-yl)ethyl]-2H-furan-5-one
SMILES (Canonical) CC12CCC(C(C1CCC(=C)C2CC(C3C=C(C(=O)O3)C=CC4C(=C)CCC5C4(CCC(C5(C)CO)O)C)C6=CCOC6=O)(C)CO)O
SMILES (Isomeric) C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2CC([C@@H]3C=C(C(=O)O3)/C=C/[C@@H]4C(=C)CC[C@H]5[C@]4(CC[C@H]([C@@]5(C)CO)O)C)C6=CCOC6=O)(C)CO)O
InChI InChI=1S/C40H56O8/c1-23-7-11-31-37(3,16-13-33(43)39(31,5)21-41)28(23)10-9-25-19-30(48-35(25)45)27(26-15-18-47-36(26)46)20-29-24(2)8-12-32-38(29,4)17-14-34(44)40(32,6)22-42/h9-10,15,19,27-34,41-44H,1-2,7-8,11-14,16-18,20-22H2,3-6H3/b10-9+/t27?,28-,29-,30+,31+,32+,33-,34-,37+,38+,39+,40+/m1/s1
InChI Key WQHWOZANSOUSAY-MHFFCXQSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C40H56O8
Molecular Weight 664.90 g/mol
Exact Mass 664.39751874 g/mol
Topological Polar Surface Area (TPSA) 134.00 Ų
XlogP 6.10
Atomic LogP (AlogP) 5.37
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 8

Synonyms

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HY-N2941
CS-0023567

2D Structure

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2D Structure of (2S)-4-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2-[2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-(5-oxo-2H-furan-4-yl)ethyl]-2H-furan-5-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9344 93.44%
Caco-2 - 0.8397 83.97%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.7247 72.47%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8588 85.88%
OATP1B3 inhibitior + 0.9315 93.15%
MATE1 inhibitior - 0.8812 88.12%
OCT2 inhibitior + 0.5876 58.76%
BSEP inhibitior + 0.9608 96.08%
P-glycoprotein inhibitior + 0.7783 77.83%
P-glycoprotein substrate + 0.5129 51.29%
CYP3A4 substrate + 0.7173 71.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8817 88.17%
CYP3A4 inhibition - 0.6915 69.15%
CYP2C9 inhibition - 0.9075 90.75%
CYP2C19 inhibition - 0.9336 93.36%
CYP2D6 inhibition - 0.9520 95.20%
CYP1A2 inhibition - 0.9268 92.68%
CYP2C8 inhibition + 0.5991 59.91%
CYP inhibitory promiscuity - 0.9332 93.32%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4559 45.59%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9121 91.21%
Skin irritation + 0.5704 57.04%
Skin corrosion - 0.9345 93.45%
Ames mutagenesis - 0.6602 66.02%
Human Ether-a-go-go-Related Gene inhibition + 0.7706 77.06%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.9009 90.09%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.6479 64.79%
Acute Oral Toxicity (c) III 0.5012 50.12%
Estrogen receptor binding + 0.7538 75.38%
Androgen receptor binding + 0.7542 75.42%
Thyroid receptor binding + 0.5246 52.46%
Glucocorticoid receptor binding + 0.6661 66.61%
Aromatase binding + 0.6289 62.89%
PPAR gamma + 0.6438 64.38%
Honey bee toxicity - 0.7062 70.62%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9870 98.70%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.78% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.67% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.50% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.43% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.30% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.96% 97.09%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.27% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.66% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.72% 94.45%
CHEMBL2581 P07339 Cathepsin D 84.82% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.86% 95.89%
CHEMBL1977 P11473 Vitamin D receptor 83.28% 99.43%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.01% 99.23%
CHEMBL204 P00734 Thrombin 82.80% 96.01%

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.
Andrographis paniculata

Cross-Links

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PubChem 139600355
LOTUS LTS0010519
wikiData Q105310729