N-sulfonyl-L-tryptophan - Compound Card

N-sulfonyl-L-tryptophan

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N-sulfonyl-L-tryptophan

Structure
Zoomed Structure
  • Family: Plantae - Mimosaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Tryptophan Derivative
Canonical Smiles OC(=O)[C@@H](Cc1cn(c2c1cccc2)S(=O)(=O)O)N
InChI InChI=1S/C11H12N2O5S/c12-9(11(14)15)5-7-6-13(19(16,17)18)10-4-2-1-3-8(7)10/h1-4,6,9H,5,12H2,(H,14,15)(H,16,17,18)/t9-/m1/s1
InChIKey XMLRQVLOMFODHA-SECBINFHSA-N
Formula C11H12N2O5S
HBA 5
HBD 3
MW 284.29
Rotatable Bonds 4
TPSA 122.62
LogP 0.25
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 284.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Entada rheedei Mimosaceae Plantae 204974

Showing of synonyms

  • Nzowa LK, Teponno RB, et al. (2013). Two new tryptophan derivatives from the seed kernels of Entada rheedei: effects on cell viability and HIV infectivity.. Fitoterapia,2013, 87, 37-42. [View] [PubMed]
Pubchem: 141174192

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 284.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.1

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.2
Plasma Protein Binding
46.3
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.94
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.19
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.92
Rat (Acute)
1.98
Rat (Chronic Oral)
2.93
Fathead Minnow
3.6
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
386.15
Hydration Free Energy
-7.74
Log(D) at pH=7.4
-2.23
Log(P)
-3.25
Log S
-1.5
Log(Vapor Pressure)
-9.16
Melting Point
219.95
pKa Acid
3.87
pKa Basic
7.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.8666
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8399
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8135
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8016
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8010
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7958
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 3 0.7909
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7792
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 3 0.7783
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7757
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7696
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 3 0.7548
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7421
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7389
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7388
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7348
Methionine--tRNA ligase P00959 SYM_ECOLI Escherichia coli 3 0.7324
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7321
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 3 0.7320
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7315
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7304
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7257
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.7238
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 4 0.7185
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7175
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7115
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7108
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 2 0.7082
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7077
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7072
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7062
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7034

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