annuolide A

Details

• Internal ID: 427c90d5-4dd2-45b4-aafa-e482815a33f3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,9aR,9bS)-9-(hydroxymethyl)-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1CCC2C(C3C1CC=C3CO)OC(=O)C2=C
• SMILES (Isomeric): C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1CC=C3CO)OC(=O)C2=C
• InChI: InChI=1S/C15H18O3/c1-8-3-5-12-9(2)15(17)18-14(12)13-10(7-16)4-6-11(8)13/h4,11-14,16H,1-3,5-7H2/t11-,12-,13-,14-/m0/s1
• InChI Key: XIKLPPAERLRBPO-XUXIUFHCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• CHEMBL496443
• CHEBI:197146
• DTXSID601105611
• (3aS,6aR,9aR,9bS)-9-(hydroxymethyl)-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]uran-2-one
• 152442-48-3
• Azuleno[4,5-b]furan-2(3H)-one, 3a,4,5,6,6a,7,9a,9b-octahydro-9-(hydroxymethyl)-3,6-bis(methylene)-, (3aS,6aR,9aR,9bS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.5894	58.94%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6153	61.53%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8998	89.98%
OATP1B3 inhibitior	+	0.9562	95.62%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9392	93.92%
P-glycoprotein inhibitior	-	0.9288	92.88%
P-glycoprotein substrate	-	0.8770	87.70%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8091	80.91%
CYP3A4 inhibition	-	0.8661	86.61%
CYP2C9 inhibition	-	0.8134	81.34%
CYP2C19 inhibition	-	0.7180	71.80%
CYP2D6 inhibition	-	0.8712	87.12%
CYP1A2 inhibition	-	0.5467	54.67%
CYP2C8 inhibition	-	0.8017	80.17%
CYP inhibitory promiscuity	-	0.8249	82.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6754	67.54%
Eye corrosion	-	0.8621	86.21%
Eye irritation	+	0.5691	56.91%
Skin irritation	-	0.6928	69.28%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6717	67.17%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7108	71.08%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6025	60.25%
Acute Oral Toxicity (c)	III	0.5162	51.62%
Estrogen receptor binding	-	0.7171	71.71%
Androgen receptor binding	+	0.6556	65.56%
Thyroid receptor binding	-	0.6500	65.00%
Glucocorticoid receptor binding	+	0.5959	59.59%
Aromatase binding	-	0.8133	81.33%
PPAR gamma	-	0.7168	71.68%
Honey bee toxicity	-	0.8581	85.81%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9288	92.88%

Targets

Proven Targets:

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	96.22%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.07%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.26%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.18%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	82.56%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.55%	100.00%

Plants that contains it

• Helianthus annuus

Cross-Links

• PubChem: 44583825
• LOTUS: LTS0154196
• wikiData: Q105328549