4a,5,5a,6,6a,6b,7,7a-Octahydro-7,7a-dihydroxy-3,6b-dimethyl-5-methylenecycloprop[2,3]indeno[5,6-b]furan-2(4H)-one

Details

• Internal ID: 2f9a04da-3206-4366-aeab-a0577b66a1c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 7,8-dihydroxy-4,9-dimethyl-13-methylidene-6-oxatetracyclo[7.4.0.03,7.010,12]tridec-3-en-5-one
• SMILES (Canonical): CC1=C2CC3C(=C)C4CC4C3(C(C2(OC1=O)O)O)C
• SMILES (Isomeric): CC1=C2CC3C(=C)C4CC4C3(C(C2(OC1=O)O)O)C
• InChI: InChI=1S/C15H18O4/c1-6-8-4-11(8)14(3)9(6)5-10-7(2)12(16)19-15(10,18)13(14)17/h8-9,11,13,17-18H,1,4-5H2,2-3H3
• InChI Key: LJLXBYGPGVKTBK-UHFFFAOYSA-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: 0.40
• Atomic LogP (AlogP): 1.14
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 73215-92-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9813	98.13%
Caco-2	-	0.6967	69.67%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6864	68.64%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.8813	88.13%
OATP1B3 inhibitior	+	0.9203	92.03%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8919	89.19%
P-glycoprotein inhibitior	-	0.9357	93.57%
P-glycoprotein substrate	-	0.8112	81.12%
CYP3A4 substrate	+	0.6552	65.52%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.7794	77.94%
CYP2C9 inhibition	-	0.7901	79.01%
CYP2C19 inhibition	-	0.7590	75.90%
CYP2D6 inhibition	-	0.8995	89.95%
CYP1A2 inhibition	-	0.6478	64.78%
CYP2C8 inhibition	-	0.8613	86.13%
CYP inhibitory promiscuity	-	0.7467	74.67%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5155	51.55%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.5677	56.77%
Skin corrosion	-	0.9027	90.27%
Ames mutagenesis	-	0.6001	60.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.4615	46.15%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5784	57.84%
skin sensitisation	-	0.7181	71.81%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6235	62.35%
Acute Oral Toxicity (c)	III	0.3029	30.29%
Estrogen receptor binding	-	0.4927	49.27%
Androgen receptor binding	+	0.6630	66.30%
Thyroid receptor binding	+	0.5354	53.54%
Glucocorticoid receptor binding	+	0.5729	57.29%
Aromatase binding	+	0.5424	54.24%
PPAR gamma	-	0.5116	51.16%
Honey bee toxicity	-	0.7153	71.53%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	95.80%	91.11%
CHEMBL240	Q12809	HERG	93.67%	89.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.62%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.67%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.63%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.87%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.70%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.21%	89.00%
CHEMBL1902	P62942	FK506-binding protein 1A	84.58%	97.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.29%	99.23%
CHEMBL1871	P10275	Androgen Receptor	81.25%	96.43%

Plants that contains it

• Sarcandra glabra

Cross-Links

• PubChem: 101603249
• NPASS: NPC186808
• LOTUS: LTS0230545
• wikiData: Q105152647