5,6,9-Trihydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

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Internal ID 553b5189-1b32-4d7d-8150-e625dd26a042
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name 5,6,9-trihydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-2-one
SMILES (Canonical) CC1(C=CC2C1C3C(CC(C2(C)O)O)C(=C)C(=O)O3)O
SMILES (Isomeric) CC1(C=CC2C1C3C(CC(C2(C)O)O)C(=C)C(=O)O3)O
InChI InChI=1S/C15H20O5/c1-7-8-6-10(16)15(3,19)9-4-5-14(2,18)11(9)12(8)20-13(7)17/h4-5,8-12,16,18-19H,1,6H2,2-3H3
InChI Key MQHMGQBWPKUXKH-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H20O5
Molecular Weight 280.32 g/mol
Exact Mass 280.13107373 g/mol
Topological Polar Surface Area (TPSA) 87.00 Ų
XlogP 0.00
Atomic LogP (AlogP) 0.15
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 5,6,9-Trihydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,9a,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 + 0.9789 97.89%
Caco-2 - 0.6378 63.78%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.5369 53.69%
OATP2B1 inhibitior - 0.8554 85.54%
OATP1B1 inhibitior + 0.8834 88.34%
OATP1B3 inhibitior + 0.9445 94.45%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.9811 98.11%
P-glycoprotein inhibitior - 0.9104 91.04%
P-glycoprotein substrate - 0.8089 80.89%
CYP3A4 substrate + 0.6007 60.07%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8522 85.22%
CYP3A4 inhibition - 0.8266 82.66%
CYP2C9 inhibition - 0.9085 90.85%
CYP2C19 inhibition - 0.8357 83.57%
CYP2D6 inhibition - 0.9267 92.67%
CYP1A2 inhibition - 0.8043 80.43%
CYP2C8 inhibition - 0.7945 79.45%
CYP inhibitory promiscuity - 0.9638 96.38%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5472 54.72%
Eye corrosion - 0.9708 97.08%
Eye irritation - 0.9532 95.32%
Skin irritation - 0.5648 56.48%
Skin corrosion - 0.8310 83.10%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5367 53.67%
Micronuclear - 0.5800 58.00%
Hepatotoxicity + 0.8824 88.24%
skin sensitisation - 0.7059 70.59%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.4822 48.22%
Acute Oral Toxicity (c) III 0.3480 34.80%
Estrogen receptor binding + 0.6155 61.55%
Androgen receptor binding + 0.5208 52.08%
Thyroid receptor binding + 0.5999 59.99%
Glucocorticoid receptor binding + 0.6842 68.42%
Aromatase binding - 0.6819 68.19%
PPAR gamma - 0.5541 55.41%
Honey bee toxicity - 0.7181 71.81%
Biodegradation - 0.5500 55.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.8954 89.54%

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 94.01% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.43% 85.14%
CHEMBL1951 P21397 Monoamine oxidase A 92.86% 91.49%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.57% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.24% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.36% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.30% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.12% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.76% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.18% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.73% 100.00%
CHEMBL299 P17252 Protein kinase C alpha 82.55% 98.03%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.04% 94.00%

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.
Ajania achilleoides

Cross-Links

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PubChem 14543457
LOTUS LTS0075731
wikiData Q105170023