2-hydroxy-4-[(4-hydroxy-2-methoxy-6-methylbenzoyl)oxy]-6-methylbenzoic acid - Compound Card

2-hydroxy-4-[(4-hydroxy-2-methoxy-6-methylbenzoyl)oxy]-6-methylbenzoic acid

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2-hydroxy-4-[(4-hydroxy-2-methoxy-6-methylbenzoyl)oxy]-6-methylbenzoic acid

Structure
Zoomed Structure
  • Family: Moraceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles COc1cc(O)cc(c1C(=O)Oc1cc(C)c(c(c1)O)C(=O)O)C
InChI InChI=1S/C17H16O7/c1-8-4-10(18)6-13(23-3)15(8)17(22)24-11-5-9(2)14(16(20)21)12(19)7-11/h4-7,18-19H,1-3H3,(H,20,21)
InChIKey HITLOWFKFPUYRR-UHFFFAOYSA-N
Formula C17H16O7
HBA 6
HBD 3
MW 332.31
Rotatable Bonds 4
TPSA 113.29
LogP 2.64
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 332.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Trilepisium madagascariense Moraceae Plantae 241931

Showing of synonyms

  • Ango YP, Kapche GDWF, et al. (2016). Three New Derivatives and Others Constituents from the Roots and Twigs of Trilepisium madagascariense DC. Helvetica Chimica Acta, 2016, 99:642-649. [View]
Pubchem: 14647825

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)Oc2ccccc2

Level: 1

Mol. Weight: 198.22 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.950
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.510
Plasma Protein Binding
58.83
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
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
6.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.240
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.680
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.970
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
3.810
Rat (Acute)
2.000
Rat (Chronic Oral)
2.730
Fathead Minnow
4.040
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
420.560
Hydration Free Energy
-11.050
Log(D) at pH=7.4
0.890
Log(P)
3.74
Log S
-4.46
Log(Vapor Pressure)
-8.69
Melting Point
202.52
pKa Acid
7.48
pKa Basic
3.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9433
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9236
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9190
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9154
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9123
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9109
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9079
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8997
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8996
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8995
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8869
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8864
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8748
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8741
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8720
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8676
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8656
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8647
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8624
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8598
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8540
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8516
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8466
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8414
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8401
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8388
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8341
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8334
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8328
Carbonic anhydrase 13 Q8N1Q1 CAH13_HUMAN Homo sapiens 3 0.8289
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8259
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8244
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8224
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8211
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8186
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8177
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8173
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8156
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8137
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8091
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8079
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8075
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8066
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8064
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8055
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8050
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8014
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8005
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8002
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7994
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7942
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7921
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7885
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7872
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7840
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7799
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7795
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7740
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7739
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7737
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7725
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7717
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7704
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7698
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7697
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7648
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7635
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7579
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7573
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7565
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7562
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7560
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7543
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7535
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 3 0.7525
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7519
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7498
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7491
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7464
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7445
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7435
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7405
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7402
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7396
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7393
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7390
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7378
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7359
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7359
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7358
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7341
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 4 0.7329
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7315
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7311
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7311
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7308
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7306
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7304
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7290
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7265
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7261
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7253
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7252
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7252
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7247
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7236
Ribosomal protein S6 kinase alpha-1 Q15418 KS6A1_HUMAN Homo sapiens 3 0.7231
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7228
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7221
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7216
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7214
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7211
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7196
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7192
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7190
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7189
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.7182
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7180
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7179
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7176
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7176
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7161
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7144
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7132
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7120
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7106
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7103
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7088
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7084
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7078
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.7071
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7054
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7052
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7051
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7044
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7043
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7040
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7035
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7025
Catechol 2,3-dioxygenase Q6REQ5 Q6REQ5_9NOCA Rhodococcus sp. DK17 3 0.7023
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7022
Type 2 DNA topoisomerase 6 subunit B O05207 TOP6B_SACSH Saccharolobus shibatae 3 0.7015
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7003
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7002

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