(4R,4aR,5S,6R,8aS,9aR)-4,6,9a-trihydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 8790205d-e308-4904-9d32-0a68c1f5687f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4R,4aR,5S,6R,8aS,9aR)-4,6,9a-trihydroxy-3,4a,5-trimethyl-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1C(CCC2C1(C(C3=C(C(=O)OC3(C2)O)C)O)C)O
• SMILES (Isomeric): C[C@@H]1[C@@H](CC[C@@H]2[C@]1([C@H](C3=C(C(=O)O[C@@]3(C2)O)C)O)C)O
• InChI: InChI=1S/C15H22O5/c1-7-11-12(17)14(3)8(2)10(16)5-4-9(14)6-15(11,19)20-13(7)18/h8-10,12,16-17,19H,4-6H2,1-3H3/t8-,9+,10-,12+,14+,15-/m1/s1
• InChI Key: ZGUSWYUSPSPSKT-WZUMYAJMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.73
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9828	98.28%
Caco-2	+	0.6015	60.15%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7058	70.58%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.9260	92.60%
OATP1B3 inhibitior	+	0.9298	92.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	-	0.8274	82.74%
P-glycoprotein inhibitior	-	0.9365	93.65%
P-glycoprotein substrate	-	0.7710	77.10%
CYP3A4 substrate	+	0.6147	61.47%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.7144	71.44%
CYP2C9 inhibition	-	0.8895	88.95%
CYP2C19 inhibition	-	0.9153	91.53%
CYP2D6 inhibition	-	0.9366	93.66%
CYP1A2 inhibition	-	0.7052	70.52%
CYP2C8 inhibition	-	0.8602	86.02%
CYP inhibitory promiscuity	-	0.8218	82.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4101	41.01%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9858	98.58%
Skin irritation	+	0.6050	60.50%
Skin corrosion	-	0.8769	87.69%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6965	69.65%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5704	57.04%
skin sensitisation	-	0.7900	79.00%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6044	60.44%
Acute Oral Toxicity (c)	III	0.3664	36.64%
Estrogen receptor binding	+	0.5671	56.71%
Androgen receptor binding	-	0.4837	48.37%
Thyroid receptor binding	+	0.5756	57.56%
Glucocorticoid receptor binding	+	0.5531	55.31%
Aromatase binding	-	0.5115	51.15%
PPAR gamma	-	0.5887	58.87%
Honey bee toxicity	-	0.8994	89.94%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9575	95.75%

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	94.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.41%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.41%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.64%	99.23%
CHEMBL2581	P07339	Cathepsin D	84.98%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.76%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.61%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.49%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.45%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.27%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.26%	89.00%

Plants that contains it

• Chloranthus anhuiensis

Cross-Links

• PubChem: 46849839
• LOTUS: LTS0063071
• wikiData: Q105375441