(E)-lespedezic acid - Compound Card

(E)-lespedezic acid

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(E)-lespedezic acid

Structure
Zoomed Structure
  • Family: Plantae - Gunneraceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC[C@H]1O[C@@H](O/C(=C/c2ccc(cc2)O)/C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C15H18O9/c16-6-10-11(18)12(19)13(20)15(24-10)23-9(14(21)22)5-7-1-3-8(17)4-2-7/h1-5,10-13,15-20H,6H2,(H,21,22)/b9-5+/t10-,11-,12+,13-,15-/m1/s1
InChIKey PLVRRSCUONTHAT-DICFCACXSA-N
Formula C15H18O9
HBA 8
HBD 6
MW 342.3
Rotatable Bonds 5
TPSA 156.91
LogP -1.37
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 342.1
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Gunnera perpensa Gunneraceae Plantae 138603

Showing of synonyms

  • Khan F, Peter XK, et al. (2004). Venusol from Gunnera perpensa: structural and activity studies. Phytochemistry, 2004, 65(8), 1117–1121. [View]
Pubchem: 14443137

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=COC2CCCCO2

Level: 1

Mol. Weight: 342.3 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 342.3 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 342.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.94
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.220
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
56.96
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
5.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.160
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.110
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
-1.860
Rat (Acute)
1.900
Rat (Chronic Oral)
3.530
Fathead Minnow
4.150
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
495.930
Hydration Free Energy
-17.330
Log(D) at pH=7.4
-2.520
Log(P)
-0.89
Log S
-1.43
Log(Vapor Pressure)
-12.04
Melting Point
163.93
pKa Acid
2.76
pKa Basic
6.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9319
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9242
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9141
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.9032
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.9002
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8966
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8930
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8759
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8637
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.8588
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8583
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8577
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8323
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8204
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8203
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8197
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8189
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8054
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8010
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7952
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7930
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7903
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 3 0.7898
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.7889
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7876
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7870
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7808
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7746
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7717
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7711
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7694
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7693
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7637
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7603
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7556
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7529
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7528
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7516
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.7452
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7410
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7368
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7343
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7342
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7288
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7246
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7217
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7165
Uncharacterized protein Q7DBA6 Q7DBA6_ECO57 Escherichia coli O157:H7 4 0.7129
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7112
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7105
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7092
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7089
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7088
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7084
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7082
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7066
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7050
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7043
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7041
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7028
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7022
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.7020

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