(3aR,6R,7aS)-3a,6-dihydroxy-1-(3-phenylprop-2-enoyl)-3,6,7,7a-tetrahydroindol-2-one

Details

• Internal ID: bb196eed-5baf-4e89-a6cb-f2b517ed34c5
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives
• IUPAC Name: (3aR,6R,7aS)-3a,6-dihydroxy-1-(3-phenylprop-2-enoyl)-3,6,7,7a-tetrahydroindol-2-one
• SMILES (Canonical): C1C(C=CC2(C1N(C(=O)C2)C(=O)C=CC3=CC=CC=C3)O)O
• SMILES (Isomeric): C1[C@H](C=C[C@]2([C@H]1N(C(=O)C2)C(=O)C=CC3=CC=CC=C3)O)O
• InChI: InChI=1S/C17H17NO4/c19-13-8-9-17(22)11-16(21)18(14(17)10-13)15(20)7-6-12-4-2-1-3-5-12/h1-9,13-14,19,22H,10-11H2/t13-,14-,17-/m0/s1
• InChI Key: OEVYGHPPCQVERC-ZQIUZPCESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₇NO₄
• Molecular Weight: 299.32 g/mol
• Exact Mass: 299.11575802 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.88
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.5962	59.62%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6330	63.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9296	92.96%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5744	57.44%
P-glycoprotein inhibitior	-	0.8907	89.07%
P-glycoprotein substrate	-	0.7988	79.88%
CYP3A4 substrate	+	0.5393	53.93%
CYP2C9 substrate	-	0.8063	80.63%
CYP2D6 substrate	-	0.8235	82.35%
CYP3A4 inhibition	-	0.9385	93.85%
CYP2C9 inhibition	-	0.8719	87.19%
CYP2C19 inhibition	-	0.8897	88.97%
CYP2D6 inhibition	-	0.9115	91.15%
CYP1A2 inhibition	-	0.8948	89.48%
CYP2C8 inhibition	-	0.7965	79.65%
CYP inhibitory promiscuity	-	0.9101	91.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4968	49.68%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9247	92.47%
Skin irritation	-	0.7649	76.49%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4918	49.18%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	-	0.5677	56.77%
skin sensitisation	-	0.8798	87.98%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6477	64.77%
Acute Oral Toxicity (c)	III	0.5445	54.45%
Estrogen receptor binding	+	0.7946	79.46%
Androgen receptor binding	+	0.7330	73.30%
Thyroid receptor binding	-	0.5507	55.07%
Glucocorticoid receptor binding	+	0.6770	67.70%
Aromatase binding	+	0.7095	70.95%
PPAR gamma	+	0.5727	57.27%
Honey bee toxicity	-	0.9072	90.72%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8374	83.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.16%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.87%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.37%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.73%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.55%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.42%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.40%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.22%	94.23%
CHEMBL5028	O14672	ADAM10	83.84%	97.50%
CHEMBL2581	P07339	Cathepsin D	83.68%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.36%	93.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.40%	96.00%

Plants that contains it

• Toussaintia orientalis

Cross-Links

• PubChem: 163074848
• LOTUS: LTS0233578
• wikiData: Q105190608