7-[[(1S,4aR,5S,6S,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy]chromen-2-one

Details

• Internal ID: b8b6ed3c-fb09-45af-b8e3-dbf89fb054bd
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 7-[[(1S,4aR,5S,6S,8aS)-6-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy]chromen-2-one
• SMILES (Canonical): CC1=CCC2C(C1COC3=CC4=C(C=C3)C=CC(=O)O4)(CCC(C2(C)CO)O)C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@]([C@H]1COC3=CC4=C(C=C3)C=CC(=O)O4)(CC[C@@H]([C@]2(C)CO)O)C
• InChI: InChI=1S/C24H30O5/c1-15-4-8-20-23(2,11-10-21(26)24(20,3)14-25)18(15)13-28-17-7-5-16-6-9-22(27)29-19(16)12-17/h4-7,9,12,18,20-21,25-26H,8,10-11,13-14H2,1-3H3/t18-,20+,21-,23+,24+/m0/s1
• InChI Key: NHFRPJOFIIVAEB-AQTBKIRRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.50 g/mol
• Exact Mass: 398.20932405 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.91
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9233	92.33%
Caco-2	-	0.5167	51.67%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7685	76.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8661	86.61%
OATP1B3 inhibitior	+	0.8382	83.82%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8026	80.26%
BSEP inhibitior	+	0.9620	96.20%
P-glycoprotein inhibitior	+	0.5991	59.91%
P-glycoprotein substrate	-	0.6557	65.57%
CYP3A4 substrate	+	0.6895	68.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8146	81.46%
CYP3A4 inhibition	-	0.6356	63.56%
CYP2C9 inhibition	-	0.8108	81.08%
CYP2C19 inhibition	-	0.6150	61.50%
CYP2D6 inhibition	-	0.9157	91.57%
CYP1A2 inhibition	+	0.5479	54.79%
CYP2C8 inhibition	-	0.5582	55.82%
CYP inhibitory promiscuity	-	0.7823	78.23%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6939	69.39%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9695	96.95%
Skin irritation	-	0.7157	71.57%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.6607	66.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.9232	92.32%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5999	59.99%
skin sensitisation	-	0.8887	88.87%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7611	76.11%
Acute Oral Toxicity (c)	III	0.4110	41.10%
Estrogen receptor binding	+	0.8147	81.47%
Androgen receptor binding	+	0.7988	79.88%
Thyroid receptor binding	+	0.7100	71.00%
Glucocorticoid receptor binding	+	0.7255	72.55%
Aromatase binding	+	0.7665	76.65%
PPAR gamma	+	0.6562	65.62%
Honey bee toxicity	-	0.8386	83.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.9908	99.08%

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	97.41%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.91%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.08%	94.00%
CHEMBL2581	P07339	Cathepsin D	90.58%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.56%	99.17%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.45%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.26%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.21%	93.99%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	87.15%	85.49%
CHEMBL1937	Q92769	Histone deacetylase 2	87.00%	94.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.55%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.27%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.78%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.48%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.55%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.27%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.16%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.04%	92.62%
CHEMBL1871	P10275	Androgen Receptor	82.24%	96.43%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.14%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.66%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	81.59%	94.73%
CHEMBL4581	P52732	Kinesin-like protein 1	81.19%	93.18%
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	80.99%	90.48%

Plants that contains it

• Ferula vesceritensis

Cross-Links

• PubChem: 102469379
• LOTUS: LTS0220569
• wikiData: Q105179364