(3R,3aS,6aR,9aR,9bS)-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Details

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Internal ID 660a582a-68c2-4c14-b88f-98401097eb75
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name (3R,3aS,6aR,9aR,9bS)-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
SMILES (Canonical) CC1C2CCC(=C)C3CCC(=C)C3C2OC1=O
SMILES (Isomeric) C[C@@H]1[C@@H]2CCC(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O
InChI InChI=1S/C15H20O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h10-14H,1-2,4-7H2,3H3/t10-,11+,12+,13+,14+/m1/s1
InChI Key UJADCNYXDHHISU-QMVSFRDZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H20O2
Molecular Weight 232.32 g/mol
Exact Mass 232.146329876 g/mol
Topological Polar Surface Area (TPSA) 26.30 Ų
XlogP 2.70
Atomic LogP (AlogP) 3.10
H-Bond Acceptor 2
H-Bond Donor 0
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,3aS,6aR,9aR,9bS)-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9974 99.74%
Caco-2 + 0.7444 74.44%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability + 0.6857 68.57%
Subcellular localzation Mitochondria 0.3746 37.46%
OATP2B1 inhibitior - 0.8555 85.55%
OATP1B1 inhibitior + 0.9040 90.40%
OATP1B3 inhibitior + 0.9350 93.50%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior - 0.8964 89.64%
P-glycoprotein inhibitior - 0.9043 90.43%
P-glycoprotein substrate - 0.8696 86.96%
CYP3A4 substrate + 0.5124 51.24%
CYP2C9 substrate - 0.7874 78.74%
CYP2D6 substrate - 0.8423 84.23%
CYP3A4 inhibition - 0.8656 86.56%
CYP2C9 inhibition - 0.9204 92.04%
CYP2C19 inhibition - 0.5187 51.87%
CYP2D6 inhibition - 0.9285 92.85%
CYP1A2 inhibition + 0.8025 80.25%
CYP2C8 inhibition - 0.9524 95.24%
CYP inhibitory promiscuity - 0.8080 80.80%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5678 56.78%
Eye corrosion - 0.7916 79.16%
Eye irritation + 0.5815 58.15%
Skin irritation - 0.5376 53.76%
Skin corrosion - 0.9452 94.52%
Ames mutagenesis - 0.7800 78.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6808 68.08%
Micronuclear - 0.8800 88.00%
Hepatotoxicity + 0.8250 82.50%
skin sensitisation + 0.5436 54.36%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity - 0.6333 63.33%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.4713 47.13%
Acute Oral Toxicity (c) III 0.6273 62.73%
Estrogen receptor binding - 0.6417 64.17%
Androgen receptor binding + 0.5247 52.47%
Thyroid receptor binding - 0.5979 59.79%
Glucocorticoid receptor binding - 0.5074 50.74%
Aromatase binding - 0.8329 83.29%
PPAR gamma - 0.8047 80.47%
Honey bee toxicity - 0.8492 84.92%
Biodegradation + 0.5250 52.50%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9846 98.46%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.80% 97.25%
CHEMBL1978 P11511 Cytochrome P450 19A1 88.14% 91.76%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.51% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.18% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.11% 97.09%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 86.72% 94.80%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 86.67% 91.11%
CHEMBL1871 P10275 Androgen Receptor 81.08% 96.43%

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.
Aucklandia costus

Cross-Links

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PubChem 10704750
LOTUS LTS0116967
wikiData Q105273810