(3aR,4R,6aR,7S,9aR,9bS)-4,7-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 16c7b648-d400-40bf-8238-a53fc72c73f9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aR,4R,6aR,7S,9aR,9bS)-4,7-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CC(C2C1C3C(C(CC2=C)O)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=C[C@@H]([C@@H]2[C@H]1[C@H]3[C@@H]([C@@H](CC2=C)O)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H18O4/c1-6-4-10(17)13-8(3)15(18)19-14(13)12-7(2)5-9(16)11(6)12/h5,9-14,16-17H,1,3-4H2,2H3/t9-,10+,11+,12-,13+,14-/m0/s1
• InChI Key: KKNGSFZDKNQHGQ-OKDXSUHISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.96
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9796	97.96%
Caco-2	-	0.6019	60.19%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4837	48.37%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8930	89.30%
OATP1B3 inhibitior	+	0.9641	96.41%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9757	97.57%
P-glycoprotein inhibitior	-	0.8806	88.06%
P-glycoprotein substrate	-	0.8807	88.07%
CYP3A4 substrate	+	0.5089	50.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.8686	86.86%
CYP2C9 inhibition	-	0.8837	88.37%
CYP2C19 inhibition	-	0.8026	80.26%
CYP2D6 inhibition	-	0.9323	93.23%
CYP1A2 inhibition	-	0.7983	79.83%
CYP2C8 inhibition	-	0.9252	92.52%
CYP inhibitory promiscuity	-	0.8617	86.17%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9425	94.25%
Carcinogenicity (trinary)	Non-required	0.4522	45.22%
Eye corrosion	-	0.9270	92.70%
Eye irritation	-	0.4832	48.32%
Skin irritation	-	0.5727	57.27%
Skin corrosion	-	0.8191	81.91%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5608	56.08%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.7870	78.70%
skin sensitisation	-	0.7522	75.22%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7010	70.10%
Acute Oral Toxicity (c)	II	0.2872	28.72%
Estrogen receptor binding	-	0.6000	60.00%
Androgen receptor binding	-	0.6143	61.43%
Thyroid receptor binding	+	0.5136	51.36%
Glucocorticoid receptor binding	+	0.5666	56.66%
Aromatase binding	-	0.8058	80.58%
PPAR gamma	-	0.7506	75.06%
Honey bee toxicity	-	0.8225	82.25%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8037	80.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.04%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.37%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.72%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.76%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.39%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.97%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.47%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.97%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.34%	86.33%

Plants that contains it

• Hymenothrix wislizeni

Cross-Links

• PubChem: 163031101
• LOTUS: LTS0046863
• wikiData: Q105142265