(3R,3aS,6aR,9aS,9bS)-6a,9a-dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,7,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

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Internal ID e2f8c2c9-4d84-4215-88ce-dedfb53a58f9
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name (3R,3aS,6aR,9aS,9bS)-6a,9a-dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,7,9b-hexahydroazuleno[4,5-b]furan-2-one
SMILES (Canonical) CC1C2CCC(=C)C3(CC=C(C3(C2OC1=O)O)C)O
SMILES (Isomeric) C[C@@H]1[C@@H]2CCC(=C)[C@@]3(CC=C([C@@]3([C@H]2OC1=O)O)C)O
InChI InChI=1S/C15H20O4/c1-8-4-5-11-10(3)13(16)19-12(11)15(18)9(2)6-7-14(8,15)17/h6,10-12,17-18H,1,4-5,7H2,2-3H3/t10-,11+,12+,14-,15+/m1/s1
InChI Key DWWAGGJXTFLIFO-NUNXZZDCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H20O4
Molecular Weight 264.32 g/mol
Exact Mass 264.13615911 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 0.30
Atomic LogP (AlogP) 1.33
H-Bond Acceptor 4
H-Bond Donor 2
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,9aS,9bS)-6a,9a-dihydroxy-3,9-dimethyl-6-methylidene-3,3a,4,5,7,9b-hexahydroazuleno[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 + 0.9549 95.49%
Caco-2 - 0.5565 55.65%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.6540 65.40%
OATP2B1 inhibitior - 0.8534 85.34%
OATP1B1 inhibitior + 0.9343 93.43%
OATP1B3 inhibitior + 0.9391 93.91%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7321 73.21%
BSEP inhibitior - 0.8083 80.83%
P-glycoprotein inhibitior - 0.9227 92.27%
P-glycoprotein substrate - 0.8847 88.47%
CYP3A4 substrate + 0.5875 58.75%
CYP2C9 substrate - 0.8093 80.93%
CYP2D6 substrate - 0.8608 86.08%
CYP3A4 inhibition - 0.8262 82.62%
CYP2C9 inhibition - 0.7922 79.22%
CYP2C19 inhibition - 0.6825 68.25%
CYP2D6 inhibition - 0.9343 93.43%
CYP1A2 inhibition - 0.5000 50.00%
CYP2C8 inhibition - 0.9082 90.82%
CYP inhibitory promiscuity - 0.9751 97.51%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5585 55.85%
Eye corrosion - 0.9831 98.31%
Eye irritation - 0.8624 86.24%
Skin irritation + 0.4948 49.48%
Skin corrosion - 0.8914 89.14%
Ames mutagenesis - 0.8700 87.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7759 77.59%
Micronuclear - 0.8300 83.00%
Hepatotoxicity + 0.7212 72.12%
skin sensitisation - 0.7909 79.09%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.4628 46.28%
Acute Oral Toxicity (c) IV 0.3427 34.27%
Estrogen receptor binding + 0.5864 58.64%
Androgen receptor binding + 0.6461 64.61%
Thyroid receptor binding - 0.5178 51.78%
Glucocorticoid receptor binding + 0.6257 62.57%
Aromatase binding - 0.6224 62.24%
PPAR gamma - 0.7078 70.78%
Honey bee toxicity - 0.8890 88.90%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9671 96.71%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.25% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.12% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.46% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.15% 100.00%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 88.15% 94.80%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.81% 93.04%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.08% 97.09%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 84.76% 86.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.21% 96.09%
CHEMBL1937 Q92769 Histone deacetylase 2 84.16% 94.75%
CHEMBL1871 P10275 Androgen Receptor 83.21% 96.43%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.49% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.68% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.58% 99.23%
CHEMBL1951 P21397 Monoamine oxidase A 80.25% 91.49%

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.
Ursinia nana

Cross-Links

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PubChem 162983984
LOTUS LTS0163906
wikiData Q104990798