(5S,5aS,8R,9bS)-5,8-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-2-one

Details

• Internal ID: e4b105e2-9332-45f8-be13-3387f05f5205
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (5S,5aS,8R,9bS)-5,8-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydrobenzo[g][1]benzofuran-2-one
• InChI: InChI=1S/C15H20O4/c1-7-9-6-11(17)15(3)5-4-10(16)8(2)12(15)13(9)19-14(7)18/h10-11,13,16-17H,4-6H2,1-3H3/t10-,11+,13+,15-/m1/s1
• InChI Key: CHTOSYWLLXTZLV-REJLFOLJSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.47
• 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	+	0.9940	99.40%
Caco-2	+	0.6853	68.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7741	77.41%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.9228	92.28%
OATP1B3 inhibitior	+	0.9364	93.64%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5179	51.79%
BSEP inhibitior	-	0.9219	92.19%
P-glycoprotein inhibitior	-	0.9172	91.72%
P-glycoprotein substrate	-	0.8594	85.94%
CYP3A4 substrate	+	0.5518	55.18%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.8675	86.75%
CYP3A4 inhibition	-	0.5833	58.33%
CYP2C9 inhibition	-	0.9269	92.69%
CYP2C19 inhibition	-	0.9258	92.58%
CYP2D6 inhibition	-	0.9425	94.25%
CYP1A2 inhibition	-	0.7047	70.47%
CYP2C8 inhibition	-	0.8284	82.84%
CYP inhibitory promiscuity	-	0.8945	89.45%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4979	49.79%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.4779	47.79%
Skin irritation	+	0.6968	69.68%
Skin corrosion	-	0.9272	92.72%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6338	63.38%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6493	64.93%
skin sensitisation	-	0.7733	77.33%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5829	58.29%
Acute Oral Toxicity (c)	III	0.5466	54.66%
Estrogen receptor binding	+	0.6015	60.15%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5441	54.41%
Glucocorticoid receptor binding	+	0.7817	78.17%
Aromatase binding	-	0.7095	70.95%
PPAR gamma	-	0.5235	52.35%
Honey bee toxicity	-	0.8824	88.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9921	99.21%

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	90.79%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.09%	85.14%
CHEMBL2581	P07339	Cathepsin D	87.59%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.55%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.85%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.63%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.65%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.12%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.24%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.80%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.69%	93.03%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	81.17%	81.11%

Plants that contains it

• Artemisia alba
• Artemisia herba-alba

Cross-Links

• PubChem: 101287064
• LOTUS: LTS0031312
• wikiData: Q104959272