2-[(3S)-3,4-dihydroxy-2-oxo-1H-indol-3-yl]acetonitrile

Details

• Internal ID: 0930eb4b-455b-4b65-a881-19e359bfd25e
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolines
• IUPAC Name: 2-[(3S)-3,4-dihydroxy-2-oxo-1H-indol-3-yl]acetonitrile
• SMILES (Canonical): C1=CC2=C(C(=C1)O)C(C(=O)N2)(CC#N)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)[C@](C(=O)N2)(CC#N)O
• InChI: InChI=1S/C10H8N2O3/c11-5-4-10(15)8-6(12-9(10)14)2-1-3-7(8)13/h1-3,13,15H,4H2,(H,12,14)/t10-/m0/s1
• InChI Key: MAPBAOFPTURBNK-JTQLQIEISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈N₂O₃
• Molecular Weight: 204.18 g/mol
• Exact Mass: 204.05349212 g/mol
• Topological Polar Surface Area (TPSA): 93.40 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.45
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	-	0.5189	51.89%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6601	66.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9375	93.75%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9068	90.68%
P-glycoprotein inhibitior	-	0.9848	98.48%
P-glycoprotein substrate	-	0.9220	92.20%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.7515	75.15%
CYP3A4 inhibition	-	0.9272	92.72%
CYP2C9 inhibition	-	0.8746	87.46%
CYP2C19 inhibition	-	0.8710	87.10%
CYP2D6 inhibition	-	0.9016	90.16%
CYP1A2 inhibition	-	0.8518	85.18%
CYP2C8 inhibition	-	0.8225	82.25%
CYP inhibitory promiscuity	-	0.7503	75.03%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6419	64.19%
Eye corrosion	-	0.9913	99.13%
Eye irritation	+	0.7564	75.64%
Skin irritation	-	0.7874	78.74%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8740	87.40%
Micronuclear	+	0.8291	82.91%
Hepatotoxicity	+	0.8051	80.51%
skin sensitisation	-	0.8264	82.64%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7154	71.54%
Acute Oral Toxicity (c)	III	0.5590	55.90%
Estrogen receptor binding	-	0.5506	55.06%
Androgen receptor binding	+	0.5288	52.88%
Thyroid receptor binding	+	0.5611	56.11%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.7487	74.87%
PPAR gamma	+	0.6221	62.21%
Honey bee toxicity	-	0.9355	93.55%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.7998	79.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.77%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.43%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.81%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	91.31%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.06%	96.09%
CHEMBL4208	P20618	Proteasome component C5	87.33%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.33%	86.33%
CHEMBL2535	P11166	Glucose transporter	83.31%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.78%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.72%	94.45%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.51%	90.24%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 60156057
• NPASS: NPC128999