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Oxitriptan

AlkaPlorer ID: AK001070

Synonym: None

IUPAC Name: (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid

Structure

SMILES: N[C@@H](CC1=CNC2=CC=C(O)C=C12)C(=O)O

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InChI: InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1

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InChIKey: LDCYZAJDBXYCGN-VIFPVBQESA-N

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Properties Information

Molecule Weight: 220.228

TPSA？: 99.34000000000002

MolLogP？: 0.8279000000000003

Number of H-Donors: 4

Number of H-Acceptors: 3

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Aspergillus fumigatus Brevianamide F prenyltransferase Activity 0.3 % 10.1021/np800501m
Aspergillus fumigatus Brevianamide F prenyltransferase Activity 1.3 % 10.1021/np800501m
Escherichia coli K-12 Beta-lactamase AmpC Potency 7079.5 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 5000.0 nM None
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 765.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 28183.8 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 44668.4 nM None
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Arachidonate 15-lipoxygenase Potency 25118.9 nM None
Homo sapiens Aryl hydrocarbon receptor Potency 39810.7 nM None
Homo sapiens Bloom syndrome protein Potency 19952.6 nM None
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 89125.1 nM None
Homo sapiens Chromobox protein homolog 1 Potency 15003.0 nM None
Homo sapiens Cyclooxygenase-1 AC50 3000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cytochrome P450 3A4 Potency 19952.6 nM None
Homo sapiens DNA polymerase iota Potency 100000.0 nM None
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 31622.8 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 39810.7 nM None
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor Potency 50118.7 nM None
Homo sapiens Glutaminase kidney isoform, mitochondrial Potency 15848.9 nM None
Homo sapiens HEK293 Potency 32629.4 nM None
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 8436.8 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 8912.5 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 22387.2 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 44668.4 nM None
Homo sapiens Histone-lysine N-methyltransferase MLL Potency 70794.6 nM None
Homo sapiens Indoleamine 2,3-dioxygenase Activity 13.0 % 10.1021/ml500385d
Homo sapiens Indoleamine 2,3-dioxygenase Activity 67.0 % 10.1021/ml500385d
Homo sapiens Indoleamine 2,3-dioxygenase Activity 100.0 % 10.1021/ml500385d
Homo sapiens Indoleamine 2,3-dioxygenase Kcat/Km 21.0 10'2/M/s 10.1021/ml500385d
Homo sapiens Indoleamine 2,3-dioxygenase Km 17000.0 nM 10.1021/ml500385d
Homo sapiens Lysine-specific demethylase 4A Potency 56234.1 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 39810.7 nM None
Homo sapiens Microtubule-associated protein tau Potency 22387.2 nM None
Homo sapiens Microtubule-associated protein tau Potency 28183.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 39810.7 nM None
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens M-phase phosphoprotein 8 Potency 794.3 nM None
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide S receptor Potency 3981.1 nM None
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 66824.2 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 12589.3 nM None
Homo sapiens Nuclear receptor ROR-gamma Potency 33491.5 nM None
Homo sapiens Peripheral myelin protein 22 Potency 84921.4 nM None
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Prelamin-A/C Potency 39.8 nM None
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Regulator of G-protein signaling 4 Potency 23778.1 nM None
Homo sapiens Regulator of G-protein signaling 4 Potency 37685.8 nM None
Homo sapiens Serine/threonine-protein kinase mTOR Potency 18492.7 nM None
Homo sapiens Serine/threonine-protein kinase mTOR Potency 23280.9 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 6469.2 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 0.91 nM 10.1016/j.bmcl.2015.02.042
Homo sapiens Serotonin 1a (5-HT1a) receptor Ki 1.8 nM 10.1016/j.bmcl.2015.07.030
Homo sapiens Serotonin 2a (5-HT2a) receptor EC50 1.349 nM 10.1021/acs.jmedchem.5b01153
Homo sapiens Serotonin 2a (5-HT2a) receptor EC50 1.9 nM 10.1021/acs.jmedchem.5b01153
Homo sapiens Serotonin 2a (5-HT2a) receptor EC50 130.0 nM 10.1016/j.bmcl.2015.07.030
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 10081.6 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor EC50 1.0 nM 10.1021/acs.jmedchem.5b01153
Homo sapiens Serotonin 2b (5-HT2b) receptor EC50 1.288 nM 10.1021/acs.jmedchem.5b01153
Homo sapiens Serotonin 2c (5-HT2c) receptor EC50 0.18 nM 10.1021/acs.jmedchem.5b01153
Homo sapiens Serotonin 2c (5-HT2c) receptor EC50 0.2188 nM 10.1021/acs.jmedchem.5b01153
Homo sapiens Serotonin 7 (5-HT7) receptor Ki 2.12 nM 10.1016/j.bmcl.2015.02.042
Homo sapiens Serotonin transporter AC50 15471.8 nM 10.1038/s41467-023-40064-9
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thyroid hormone receptor beta-1 Potency 0.7 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 5011.9 nM None
Homo sapiens Tryptophan 2,3-dioxygenase Activity 0.0 % 10.1021/ml500385d
Homo sapiens Tryptophan 2,3-dioxygenase Activity 14.0 % 10.1021/ml500385d
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Influenza A virus Nonstructural protein 1 Potency 39810.7 nM None
Mus musculus Nuclear receptor ROR-gamma Potency 11220.2 nM None
Photinus pyralis Luciferin 4-monooxygenase Potency 32196.8 nM None
Photinus pyralis Luciferin 4-monooxygenase Potency 37933.0 nM None
Plasmodium falciparum Plasmodium falciparum Potency 11689.1 nM None
Plasmodium falciparum Plasmodium falciparum Potency 18526.0 nM None
Rattus norvegicus Amino acid transporter Inhibition 25.0 % None
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 4466.8 nM None
Rattus norvegicus Serotonin 3 (5-HT3) receptor Ki 158.49 nM 10.1016/S0960-894X(01)81243-9
Rattus norvegicus Serotonin 4 (5-HT4) receptor EC50 9.772 nM 10.1016/S0960-894X(01)81243-9
Rattus norvegicus Serotonin 4 (5-HT4) receptor Intrinsic activity 1.0 None 10.1016/S0960-894X(01)81243-9
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 15003.0 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 17782.8 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 21192.3 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 39810.7 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 44668.4 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 3.378 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1749 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.02 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.91 % 10.21203/rs.3.rs-23951/v1
Trypanosoma brucei 6-phospho-1-fructokinase Potency 7568.6 nM None
None Molecular identity unknown Potency 74978.0 nM None
None No relevant target Retention_time 5.1 min 10.1021/ml500385d
None Unchecked Ac50 0.631 uM None
None Unchecked Ac50 19.95 uM None
None Unchecked AC50 631.0 nM None
None Unchecked AC50 19952.6 nM None
None Unchecked Activity 0.3 % 10.1021/np800501m
None Unchecked Activity 0.8 % 10.1021/np800501m
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Potency 70.8 nM None
None Unchecked Potency 2511.9 nM None
None Unchecked Potency 17782.8 nM None
None Unchecked Potency 32642.7 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT002126 CC(=O)C(=O)O.N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>O=C(O)C(=O)Cc1c[nH]c2ccc(O)cc12 enzymemap_42441
AKRT005235 CC(C)=CCOP(=O)(O)OP(=O)(O)O.N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>CC(C)=CCc1c(O)ccc2[nH]cc(C[C@H](N)C(=O)O)c12 enzymemap_40437
AKRT005236 CC(C)=CCOP(=O)(O)OP(=O)(O)O.N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>CC(C)=CCc1cc(O)cc2c(C[C@H](N)C(=O)O)c[nH]c12 enzymemap_41285
AKRT014677 C[SAH].N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>Cc1[nH]c2ccc(O)cc2c1C[C@H](N)C(=O)O enzymemap_25748
AKRT019495 N[C@@H](CO)C(=O)O.Oc1ccc2[nH]ccc2c1>>N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O enzymemap_83801
AKRT019712 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)CCC(=O)C(=O)O>>N[C@@H](CCC(=O)O)C(=O)O R02700
AKRT019713 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=C(O)CCC(=O)C(=O)O>>O=C(O)C(=O)Cc1c[nH]c2ccc(O)cc12 R02700
AKRT019714 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O.O=CC(=O)O>>O=C(O)C(=O)Cc1c[nH]c2ccc(O)cc12 enzymemap_42619
AKRT019715 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>C[C@H](N)C(=O)O enzymemap_42441
AKRT019716 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>NC(=O)Cc1c[nH]c2ccc(O)cc12 enzymemap_10425
AKRT019717 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>NCC(=O)O enzymemap_42619
AKRT019718 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>NCCc1c[nH]c2ccc(O)cc12 RXN3DJ-170
AKRT019719 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>NCCc1c[nH]c2ccc(O)cc12.O=C=O None
AKRT019720 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>N[C@@H](CC(=O)c1cc(O)ccc1NC=O)C(=O)O R02702
AKRT019721 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>O=C(O)C(=O)Cc1c[nH]c2ccc(O)cc12 enzymemap_41895
AKRT019722 N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O>>O=C=O RXN3DJ-170
AKRT019799 N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O>>N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O TRYPTOPHAN-5-MONOOXYGENASE-RXN