(4aR,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-4,4a,5,9-tetrahydrobenzo[f][1]benzofuran-2,8-dione

Details

• Internal ID: 7ce177e0-4b5b-4c04-b19d-ac348c4ebddd
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (4aR,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-4,4a,5,9-tetrahydrobenzo[f][1]benzofuran-2,8-dione
• SMILES (Canonical): CC1=C2CC3CC=CC(=O)C3(CC2(OC1=O)O)C
• SMILES (Isomeric): CC1=C2C[C@H]3CC=CC(=O)[C@@]3(C[C@@]2(OC1=O)O)C
• InChI: InChI=1S/C14H16O4/c1-8-10-6-9-4-3-5-11(15)13(9,2)7-14(10,17)18-12(8)16/h3,5,9,17H,4,6-7H2,1-2H3/t9-,13-,14+/m1/s1
• InChI Key: JHBATSSGORALFQ-FZQKWOKYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.27 g/mol
• Exact Mass: 248.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.49
• 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	+	0.9966	99.66%
Caco-2	+	0.7596	75.96%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7229	72.29%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9089	90.89%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8678	86.78%
P-glycoprotein inhibitior	-	0.9613	96.13%
P-glycoprotein substrate	-	0.8459	84.59%
CYP3A4 substrate	+	0.5925	59.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8905	89.05%
CYP3A4 inhibition	-	0.6792	67.92%
CYP2C9 inhibition	-	0.9100	91.00%
CYP2C19 inhibition	-	0.9552	95.52%
CYP2D6 inhibition	-	0.9627	96.27%
CYP1A2 inhibition	-	0.8200	82.00%
CYP2C8 inhibition	-	0.8423	84.23%
CYP inhibitory promiscuity	-	0.9342	93.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4134	41.34%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.7623	76.23%
Skin irritation	+	0.5607	56.07%
Skin corrosion	-	0.8557	85.57%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5675	56.75%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.7286	72.86%
skin sensitisation	-	0.7396	73.96%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.6229	62.29%
Acute Oral Toxicity (c)	III	0.3166	31.66%
Estrogen receptor binding	-	0.7314	73.14%
Androgen receptor binding	+	0.5857	58.57%
Thyroid receptor binding	-	0.5566	55.66%
Glucocorticoid receptor binding	-	0.5782	57.82%
Aromatase binding	-	0.6181	61.81%
PPAR gamma	-	0.6114	61.14%
Honey bee toxicity	-	0.9024	90.24%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9912	99.12%

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	97.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.11%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.82%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.81%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.94%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.55%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.77%	89.00%
CHEMBL4208	P20618	Proteasome component C5	84.35%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.88%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.08%	97.14%

Plants that contains it

• Siphonochilus aethiopicus

Cross-Links

• PubChem: 163074393
• LOTUS: LTS0254541
• wikiData: Q105127843