(3S,3aR,4S,6aR,9aR,9bR)-4-hydroxy-3-methyl-6,9-dimethylidene-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione

Details

• Internal ID: 02a7cdc8-aefa-4006-be84-4d677eb266ce
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aR,4S,6aR,9aR,9bR)-4-hydroxy-3-methyl-6,9-dimethylidene-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2C(CC(=C)C3CC(=O)C(=C)C3C2OC1=O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=C)[C@@H]3CC(=O)C(=C)[C@@H]3[C@H]2OC1=O)O
• InChI: InChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h8-9,11-14,17H,1-2,4-5H2,3H3/t8-,9-,11-,12-,13+,14+/m0/s1
• InChI Key: MCRCUBNJZBCTGB-MQFSHEFBSA-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): 63.60 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.25
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	+	0.5642	56.42%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5603	56.03%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9391	93.91%
P-glycoprotein inhibitior	-	0.9038	90.38%
P-glycoprotein substrate	-	0.7643	76.43%
CYP3A4 substrate	+	0.5296	52.96%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.8180	81.80%
CYP2C9 inhibition	-	0.9149	91.49%
CYP2C19 inhibition	-	0.8750	87.50%
CYP2D6 inhibition	-	0.9592	95.92%
CYP1A2 inhibition	-	0.7817	78.17%
CYP2C8 inhibition	-	0.9541	95.41%
CYP inhibitory promiscuity	-	0.9571	95.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9325	93.25%
Carcinogenicity (trinary)	Non-required	0.4722	47.22%
Eye corrosion	-	0.8990	89.90%
Eye irritation	-	0.5444	54.44%
Skin irritation	-	0.5225	52.25%
Skin corrosion	-	0.8273	82.73%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7369	73.69%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.7212	72.12%
skin sensitisation	-	0.7257	72.57%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7841	78.41%
Acute Oral Toxicity (c)	II	0.3829	38.29%
Estrogen receptor binding	-	0.5961	59.61%
Androgen receptor binding	-	0.5455	54.55%
Thyroid receptor binding	-	0.6467	64.67%
Glucocorticoid receptor binding	-	0.5830	58.30%
Aromatase binding	-	0.7324	73.24%
PPAR gamma	-	0.7549	75.49%
Honey bee toxicity	-	0.7546	75.46%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9325	93.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.36%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.27%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.99%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.84%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.56%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.55%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.88%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.74%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%

Plants that contains it

• Pseudostifftia kingii

Cross-Links

• PubChem: 162993250
• LOTUS: LTS0011857
• wikiData: Q105161382