4-[(2R,3aR,5aS,6R,7R,9aR,9bS)-7-hydroxy-6-(hydroxymethyl)-3a,6,9a-trimethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran-2-yl]-2H-furan-5-one

Details

• Internal ID: 9c98291c-2e17-40ec-9bbf-e7dc7ae5c37c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[(2R,3aR,5aS,6R,7R,9aR,9bS)-7-hydroxy-6-(hydroxymethyl)-3a,6,9a-trimethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran-2-yl]-2H-furan-5-one
• SMILES (Canonical): CC12CCC(C(C1CCC3(C2CC(O3)C4=CCOC4=O)C)(C)CO)O
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@]([C@H]1CC[C@@]3([C@H]2C[C@@H](O3)C4=CCOC4=O)C)(C)CO)O
• InChI: InChI=1S/C20H30O5/c1-18-7-5-16(22)19(2,11-21)14(18)4-8-20(3)15(18)10-13(25-20)12-6-9-24-17(12)23/h6,13-16,21-22H,4-5,7-11H2,1-3H3/t13-,14+,15+,16-,18-,19+,20-/m1/s1
• InChI Key: QTYVPMSAPQBXMM-AZFOIECZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.20932405 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.20
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9659	96.59%
Caco-2	+	0.5907	59.07%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7582	75.82%
OATP2B1 inhibitior	-	0.8673	86.73%
OATP1B1 inhibitior	+	0.9267	92.67%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.8412	84.12%
OCT2 inhibitior	-	0.7602	76.02%
BSEP inhibitior	+	0.8078	80.78%
P-glycoprotein inhibitior	-	0.7142	71.42%
P-glycoprotein substrate	-	0.7536	75.36%
CYP3A4 substrate	+	0.6548	65.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8778	87.78%
CYP3A4 inhibition	-	0.8366	83.66%
CYP2C9 inhibition	-	0.9198	91.98%
CYP2C19 inhibition	-	0.9261	92.61%
CYP2D6 inhibition	-	0.9475	94.75%
CYP1A2 inhibition	-	0.9368	93.68%
CYP2C8 inhibition	-	0.7438	74.38%
CYP inhibitory promiscuity	-	0.8775	87.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4703	47.03%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9459	94.59%
Skin irritation	-	0.5142	51.42%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.7111	71.11%
Human Ether-a-go-go-Related Gene inhibition	-	0.5476	54.76%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5577	55.77%
skin sensitisation	-	0.9119	91.19%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6468	64.68%
Acute Oral Toxicity (c)	I	0.6063	60.63%
Estrogen receptor binding	+	0.8533	85.33%
Androgen receptor binding	+	0.6624	66.24%
Thyroid receptor binding	+	0.6970	69.70%
Glucocorticoid receptor binding	+	0.8972	89.72%
Aromatase binding	+	0.8138	81.38%
PPAR gamma	+	0.5695	56.95%
Honey bee toxicity	-	0.8282	82.82%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9707	97.07%

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	95.23%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.56%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.82%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.30%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.35%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.61%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.07%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.38%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.10%	90.17%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 101563020
• LOTUS: LTS0003573
• wikiData: Q105227988