Trilepisuimic acid - Compound Card

Trilepisuimic acid

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Trilepisuimic acid

Structure
Zoomed Structure
  • Family: Moraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Terpene
Canonical Smiles O=C(Oc1ccc(cc1O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C16H12O7/c17-11-4-1-9(7-12(11)18)2-6-15(20)23-14-5-3-10(16(21)22)8-13(14)19/h1-8,17-19H,(H,21,22)/b6-2+
InChIKey BMDBIOFBSSWKCK-QHHAFSJGSA-N
Formula C16H12O7
HBA 6
HBD 4
MW 316.27
Rotatable Bonds 4
TPSA 124.29
LogP 2.12
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 316.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Trilepisium madagascariense Moraceae Plantae 241931

Showing of synonyms

  • Ango P, Kapche D, et al. (2012). Chemical constituents of Trilepisium madagascariense (Moraceae) and their antimicrobial activity. Phytochemistry Letters, 2012, 5(3), 524-528. [View]
Pubchem: 139329499

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 224.26 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.29
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
55.46
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
12.3
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.11
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.27
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.02
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
3.08
Rat (Acute)
2.18
Rat (Chronic Oral)
3.18
Fathead Minnow
4.0
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
450.51
Hydration Free Energy
-11.29
Log(D) at pH=7.4
0.68
Log(P)
2.31
Log S
-2.84
Log(Vapor Pressure)
-9.33
Melting Point
249.61
pKa Acid
5.91
pKa Basic
3.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9495
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.9395
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9349
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9113
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9060
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9043
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9016
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.9015
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9011
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8961
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8908
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8871
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8709
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8685
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8571
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8454
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8365
Nucleoside diphosphate kinase Q5HFV4 NDK_STAAC Staphylococcus aureus 3 0.8360
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8289
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.8283
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8278
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8264
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8257
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8242
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8232
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8230
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8219
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8209
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8147
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8142
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8101
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.8043
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7972
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7967
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7922
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7920
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7886
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7845
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7841
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7815
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7799
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7781
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7759
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.7752
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7735
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7727
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7680
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7671
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7664
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7637
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7629
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7628
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7603
2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase Q988D3 Q988D3_RHILO Mesorhizobium japonicum) 3 0.7582
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7569
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7563
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7525
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7500
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.7500
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7499
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.7495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7491
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7489
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7486
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7449
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7446
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7433
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7423
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7414
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7389
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7389
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7363
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7363
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7356
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7332
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7326
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7319
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7300
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7257
RNA-directed RNA polymerase P11124 RDRP_BPPH6 Pseudomonas phage phi6 3 0.7249
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7245
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7236
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7222
Pol polyprotein Q90K99 Q90K99_9HIV1 Human immunodeficiency virus 1 3 0.7184
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7182
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.7163
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7156
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7156
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 4 0.7146
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7145
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7141
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7137
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7137
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7135
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7135
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7124
L-methionine gamma-lyase P13254 MEGL_PSEPU Pseudomonas putida 3 0.7122
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7122
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7106
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7100
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7098
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7096
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7094
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7092
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7087
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7082
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7081
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7076
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7074
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7072
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 2 0.7071
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7066
Probable tRNA(His) guanylyltransferase Q9NWX6 THG1_HUMAN Homo sapiens 3 0.7061
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7046
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7044
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7025
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7024
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7022
Glycine N-methyltransferase P13255 GNMT_RAT Rattus norvegicus 4 0.7021
eIF-2-alpha kinase GCN2 P15442 GCN2_YEAST Saccharomyces cerevisiae 3 0.7015
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7010

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