1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

Details

• Internal ID: c684d67e-b9cd-45ae-90da-e4e6545d0d25
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• InChI: InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)
• InChI Key: ZUPHXNBLQCSEIA-UHFFFAOYSA-N
• Popularity: 86 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄N₂O₂
• Molecular Weight: 230.26 g/mol
• Exact Mass: 230.105527694 g/mol
• Topological Polar Surface Area (TPSA): 65.10 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 2
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• Tetrahydroharman-3-carboxylic acid
• 1H-Pyrido[3,4-b]indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-methyl-
• 1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
• 1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
• 7FCJ1OW7OX
• 1H-Pyrido(3,4-b)indole-3-carboxylic acid, 2,3,4,9-tetrahydro-1-methyl-
• 1-methyl-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid
• MTCA
• RefChem:907661
• 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• 1-Methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid
• MFCD00022199
• 1,2,3,4-tetrahydroharman-3-carboxylic acid
• Harmane-1,2,3,4-tetrahydro-3-carboxylic acid
• Harmane 1,2,3,4 tetrahydro-3-carboxylic acid
• 1-Methyl-tetrahydro-beta-carboline-3-carboxylic acid
• 1-Methyl-1,2,3,4-Tetrahydropyrido[3,4-b]indole-3-carboxylic acid
• NSC26225
• (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid
• 1-Methyl-2,3,4,9-tetrahydro-1H-1-carboline-3-carboxylic acid
• Tryptophan EP Impurity I
• 1,2,3,4-Tetrahydroharmane-3-carboxylic acid
• UNII-7FCJ1OW7OX
• ChemDiv1_000460
• 1-methyl-1,2,3,4-tetrahydrobeta-carboline-3-carboxylic acid
• 1-Methyl-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid
• CCRIS 6487
• 2,3,4,9-Tetrahydro-1-methyl-1H-pyrido[3,4-b]indole-3-carboxylic acid
• NSC 26225
• Cambridge id 5147364
• CBDivE_001615
• CBDivE_003491
• SCHEMBL504399
• CHEMBL491388
• SCHEMBL29379056
• HMS588E20
• CHEBI:172470
• 667N6AT8F2
• DTXSID401023900
• ALBB-021229
• NSC-26225
• NSC298851
• NSC298854
• SBB027286
• STK386725
• AKOS000265198
• AKOS016037534
• AKOS016038054
• AKOS024267136
• 1,2,3,4-Tetrahydro-3-carboxyharmane
• FH56799
• NSC-298851
• NSC-298854
• SB47569
• SDCCGMLS-0064537.P001
• 1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, sodium nitrite treated
• NCGC00163354-01
• 1234_Tetrahydroharmane_3_carboxylic_acid
• BS-37974
• ST053494
• SY079071
• Harmane 1,3,4 tetrahydro-3-carboxylic acid
• EN300-235652
• F87977
• AE-473/31198040
• AE-641/00198040
• F307993
• N-ACETYLTRYPTOPHAN IMPURITY I [EP IMPURITY]
• F0896-0475
• F1918-0045
• Tryptophan EP Impurity I; N-Acetyltryptophan EP Impurity I
• 1-Methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid #
• 1-METHYL-1,2,3,4-TETRAHYDRO-9H-.BETA.-CARBOLINE-3-CARBOXYLIC ACID
• 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-3-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	-	0.8209	82.09%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6647	66.47%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9168	91.68%
OATP1B3 inhibitior	+	0.9466	94.66%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7567	75.67%
BSEP inhibitior	-	0.6351	63.51%
P-glycoprotein inhibitior	-	0.9816	98.16%
P-glycoprotein substrate	-	0.8021	80.21%
CYP3A4 substrate	+	0.5105	51.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7125	71.25%
CYP3A4 inhibition	-	0.8553	85.53%
CYP2C9 inhibition	-	0.9414	94.14%
CYP2C19 inhibition	-	0.8615	86.15%
CYP2D6 inhibition	+	0.5802	58.02%
CYP1A2 inhibition	-	0.6111	61.11%
CYP2C8 inhibition	-	0.7789	77.89%
CYP inhibitory promiscuity	-	0.8793	87.93%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7419	74.19%
Eye corrosion	-	0.9948	99.48%
Eye irritation	-	0.9287	92.87%
Skin irritation	-	0.8014	80.14%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7108	71.08%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.5091	50.91%
skin sensitisation	-	0.9023	90.23%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7055	70.55%
Acute Oral Toxicity (c)	III	0.5018	50.18%
Estrogen receptor binding	-	0.6506	65.06%
Androgen receptor binding	-	0.5493	54.93%
Thyroid receptor binding	-	0.7564	75.64%
Glucocorticoid receptor binding	-	0.7055	70.55%
Aromatase binding	-	0.5502	55.02%
PPAR gamma	+	0.7606	76.06%
Honey bee toxicity	-	0.9509	95.09%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	-	0.5535	55.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.06%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.92%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.21%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.78%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.60%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.51%	99.23%
CHEMBL2535	P11166	Glucose transporter	85.36%	98.75%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.87%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.76%	89.00%
CHEMBL5028	O14672	ADAM10	82.53%	97.50%

Plants that contains it

• Lepidium meyenii
• Oxalis pes-caprae

Cross-Links

• PubChem: 73530
• LOTUS: LTS0109221
• wikiData: Q105384022