3-hydroxy-3-methylbutyl anthranilate - Compound Card

3-hydroxy-3-methylbutyl anthranilate

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3-hydroxy-3-methylbutyl anthranilate

Structure
Zoomed Structure
  • Family: Fungi - Montagnulaceae
  • Kingdom: Fungi
  • Class: Phenolic
    • Subclass: Phenolic Ester
Canonical Smiles O=C(c1ccccc1N)OCCC(O)(C)C
InChI InChI=1S/C12H17NO3/c1-12(2,15)7-8-16-11(14)9-5-3-4-6-10(9)13/h3-6,15H,7-8,13H2,1-2H3
InChIKey ZEHUWEMRGCVXGB-UHFFFAOYSA-N
Formula C12H17NO3
HBA 4
HBD 2
MW 223.27
Rotatable Bonds 4
TPSA 72.55
LogP 1.59
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 223.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dendrothyrium variisporum Montagnulaceae Fungi 1985348

Showing of synonyms

  • Teponno RB, Noumeur SR, et al. (2017). Furanones and anthranilic acid derivatives from the endophytic fungus Dendrothyrium variisporum. Molecules 2017, 22(10), 1674. [View] [PubMed]
Pubchem: 79356037

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 223.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.31
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.26
Plasma Protein Binding
11.27
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.39
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.88
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
2.41
Rat (Acute)
1.71
Rat (Chronic Oral)
2.14
Fathead Minnow
3.94
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
298.19
Hydration Free Energy
-10.53
Log(D) at pH=7.4
1.49
Log(P)
2.3
Log S
-2.03
Log(Vapor Pressure)
-4.65
Melting Point
91.34
pKa Acid
9.65
pKa Basic
5.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.9764
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.9506
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9064
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8956
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8915
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8870
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8851
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8835
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8743
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8741
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8731
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8690
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.8657
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8596
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.8399
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8380
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8367
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8352
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8261
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8174
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8153
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8098
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8069
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8056
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8039
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8034
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.8033
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7963
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7943
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7792
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7790
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7768
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7764
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7743
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7743
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7732
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7714
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7631
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7604
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7601
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7587
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7574
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7572
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7560
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7527
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7524
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7518
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7493
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7491
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7490
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7482
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7476
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7473
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7459
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7457
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7444
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7439
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7439
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7434
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7433
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7412
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7406
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7390
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7388
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7383
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 2 0.7376
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7374
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7368
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7352
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7350
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7346
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7331
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7329
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7326
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7320
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7315
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7310
3-oxoacyl-[acyl-carrier-protein] synthase 1 Q2YQQ9 Q2YQQ9_BRUA2 Brucella abortus 3 0.7310
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7305
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7299
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7299
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7292
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7289
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7273
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7270
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7255
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7243
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7237
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7233
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7222
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7216
Sphingosine 1-phosphate receptor 1 P21453 S1PR1_HUMAN Homo sapiens 3 0.7203
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7195
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2 O95340 PAPS2_HUMAN Homo sapiens 2 0.7189
Chromosome-associated kinesin KIF4 P33174 KIF4_MOUSE Mus musculus 2 0.7188
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7187
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 2 0.7187
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7185
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7184
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7182
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7181
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7181
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7180
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7179
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7176
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7176
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7176
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7172
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7164
Genome polyprotein P27395 POLG_JAEV1 Japanese encephalitis virus 2 0.7163
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7162
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7154
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7147
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7146
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7134
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7131
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7125
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7125
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7119
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7117
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 2 0.7108
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7095
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7095
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7095
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7094
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7092
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7080
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 2 0.7078
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7074
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 3 0.7073
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7071
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7071
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7066
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7062
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7046
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7039
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7034
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7032
Anthranilate phosphoribosyltransferase P50384 TRPD_SACS2 Saccharolobus solfataricus 2 0.7022
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7020
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7015
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7010
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7005
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7001

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