(1S,4R,4aS,8R,8aR)-4,8-diacetyloxy-2-formyl-1-hydroxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalene-1-carboxylic acid

Details

• Internal ID: d1cb82b9-8f51-4bf1-9964-467182abd659
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: (1S,4R,4aS,8R,8aR)-4,8-diacetyloxy-2-formyl-1-hydroxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=O)OC1CCC(C2C1(C(C(=CC2OC(=O)C)C=O)(C(=O)O)O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1CCC([C@H]2[C@]1([C@](C(=C[C@H]2OC(=O)C)C=O)(C(=O)O)O)C)(C)C
• InChI: InChI=1S/C19H26O8/c1-10(21)26-13-8-12(9-20)19(25,16(23)24)18(5)14(27-11(2)22)6-7-17(3,4)15(13)18/h8-9,13-15,25H,6-7H2,1-5H3,(H,23,24)/t13-,14-,15+,18+,19+/m1/s1
• InChI Key: BMWBMNGRDVKNHG-GVYRHCHYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₈
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.16276778 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.25
• H-Bond Acceptor: 7
• 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	+	0.9663	96.63%
Caco-2	-	0.5426	54.26%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8084	80.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8013	80.13%
OATP1B3 inhibitior	+	0.8589	85.89%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7657	76.57%
P-glycoprotein inhibitior	-	0.6442	64.42%
P-glycoprotein substrate	-	0.7364	73.64%
CYP3A4 substrate	+	0.6175	61.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9086	90.86%
CYP3A4 inhibition	-	0.8301	83.01%
CYP2C9 inhibition	-	0.8277	82.77%
CYP2C19 inhibition	-	0.8652	86.52%
CYP2D6 inhibition	-	0.9178	91.78%
CYP1A2 inhibition	-	0.6498	64.98%
CYP2C8 inhibition	-	0.5743	57.43%
CYP inhibitory promiscuity	-	0.9182	91.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.5741	57.41%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9137	91.37%
Skin irritation	+	0.5183	51.83%
Skin corrosion	-	0.9204	92.04%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5545	55.45%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6676	66.76%
skin sensitisation	-	0.6071	60.71%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6436	64.36%
Acute Oral Toxicity (c)	III	0.5844	58.44%
Estrogen receptor binding	+	0.7216	72.16%
Androgen receptor binding	+	0.5384	53.84%
Thyroid receptor binding	+	0.5136	51.36%
Glucocorticoid receptor binding	+	0.5666	56.66%
Aromatase binding	-	0.5093	50.93%
PPAR gamma	+	0.5796	57.96%
Honey bee toxicity	-	0.8716	87.16%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6755	67.55%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.30%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.43%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.33%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.30%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.58%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	85.73%	91.19%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.93%	94.08%
CHEMBL5028	O14672	ADAM10	84.31%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.71%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.33%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.43%	100.00%

Plants that contains it

• Pleodendron costaricense

Cross-Links

• PubChem: 163103544
• LOTUS: LTS0194031
• wikiData: Q104938620