2,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid

Details

• Internal ID: 63105ca0-c661-4b1e-819e-ec3a2ffb3d71
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• SMILES (Canonical): C1C(NCC2=C1C3=CC=CC=C3N2)C(=O)O
• SMILES (Isomeric): C1C(NCC2=C1C3=CC=CC=C3N2)C(=O)O
• InChI: InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)
• InChI Key: FSNCEEGOMTYXKY-UHFFFAOYSA-N
• Popularity: 67 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.24 g/mol
• Exact Mass: 216.089877630 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• 2,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid
• 1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid
• 1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
• CCRIS 6486
• NSC 96912
• CK2W5X3J2K
• Tetrahydro-beta-carboline-3-carboxylic acid
• MFCD00204332
• NSC-96912
• L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid
• 2,3,4,9-TETRAHYDRO-1H-b-CARBOLINE-3-CARBOXYLIC ACID
• H-D-Tpi-OH;D-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid;D-Tryptoline-3-carboxylic acid;D-1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid
• Maybridge1_002151
• H-Tpi-OH;L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid;L-Tryptoline-3-carboxylic acid;L-1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid
• 1H-Pyrido(3,4-b)indole-3-carboxylic acid, 2,3,4,9-tetrahydro-
• DL-Tpi-OH
• ChemDiv1_000471
• UNII-CK2W5X3J2K
• CBDivE_002277
• CBDivE_005090
• SCHEMBL416558
• CHEMBL149177
• beta-Carbocine-3-carboxylic acid
• CHEBI:91151
• FSNCEEGOMTYXKY-UHFFFAOYSA-
• HMS547J17
• HMS588F09
• DTXSID401032096
• .beta.-Carbocine-3-carboxylic acid
• NSC96912
• CCG-41295
• STK387520
• AKOS000273957
• AKOS016038051
• Carboline base + 4H, carboxylic acid
• AM83757
• MS-1161
• SB45333
• SDCCGMLS-0065883.P001
• LS-133456
• TRYPTOPHAN IMPURITY H [EP IMPURITY]
• 3-Carboxy-1,2,3,4-tetrahydro-2-carboline
• BB 0218166
• CS-0020443
• EU-0001445
• FT-0651518
• FT-0651519
• FT-0705298
• 3-Carboxy-1,2,3,4-tetrahydro-beta-carboline
• EN300-111082
• AF-399/25070003
• D-1,2,3,4-tetrahydronorharmane-3-carboxylicacid
• SR-01000399955
• (-)-3-Carboxy-1,2,3,4-tetrahydro-beta-carboline
• N-ACETYLTRYPTOPHAN IMPURITY H [EP IMPURITY]
• SR-01000399955-1
• SR-01000399955-2
• DL-1,2,3,4-TETRAHYDRO-3-CARBOXY-2-CARBOLINE
• Q27163087
• Z56762879
• 2,3,4,9-Tetrahydro-1H-ss-carboline-3-carboxylic acid
• F0037-1026
• (+/-)-1,2,3,4-TETRAHYDRO-3-CARBOXY-2-CARBOLINE
• 1,2,3,4-tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid
• 2,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid #
• (3RS)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
• 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylicacid
• (3RS)-1,2,3,4-TETRAHYDRO-9H-.BETA.-CARBOLINE-3-CARBOXYLIC ACID
• InChI=1/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	-	0.5505	55.05%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6431	64.31%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9406	94.06%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7338	73.38%
P-glycoprotein inhibitior	-	0.9867	98.67%
P-glycoprotein substrate	-	0.8730	87.30%
CYP3A4 substrate	-	0.5370	53.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6662	66.62%
CYP3A4 inhibition	-	0.9636	96.36%
CYP2C9 inhibition	-	0.9544	95.44%
CYP2C19 inhibition	-	0.8246	82.46%
CYP2D6 inhibition	-	0.5087	50.87%
CYP1A2 inhibition	+	0.5473	54.73%
CYP2C8 inhibition	-	0.7581	75.81%
CYP inhibitory promiscuity	-	0.9558	95.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7932	79.32%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.6616	66.16%
Skin irritation	-	0.7965	79.65%
Skin corrosion	-	0.9575	95.75%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6331	63.31%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.5091	50.91%
skin sensitisation	-	0.8858	88.58%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7587	75.87%
Acute Oral Toxicity (c)	III	0.5172	51.72%
Estrogen receptor binding	-	0.7151	71.51%
Androgen receptor binding	-	0.4928	49.28%
Thyroid receptor binding	-	0.7509	75.09%
Glucocorticoid receptor binding	-	0.7151	71.51%
Aromatase binding	-	0.5774	57.74%
PPAR gamma	+	0.7029	70.29%
Honey bee toxicity	-	0.9071	90.71%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.5438	54.38%

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	92.17%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.70%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.87%	94.62%
CHEMBL2535	P11166	Glucose transporter	89.52%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.38%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	88.29%	91.49%
CHEMBL2581	P07339	Cathepsin D	88.13%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.68%	94.23%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.59%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.80%	94.08%
CHEMBL5028	O14672	ADAM10	81.91%	97.50%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.80%	88.56%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 98285
• NPASS: NPC15573
• ChEMBL: CHEMBL149177
• LOTUS: LTS0197028
• wikiData: Q27163087