6-(4-hydroxy)-E-cinnamate - Compound Card

6-(4-hydroxy)-E-cinnamate

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6-(4-hydroxy)-E-cinnamate

Structure
Zoomed Structure
  • Family: Convolvulaceae
  • Kingdom: Plantae
  • Class: Phenylpropanoid
    • Subclass: Cyanogenic Diglucoside
Canonical Smiles [O-]C(=O)/C=C\c1ccc(cc1)O
InChI InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/p-1/b6-3-
InChIKey NGSWKAQJJWESNS-UTCJRWHESA-M
Formula C9H7O3-
HBA 3
HBD 1
MW 163.15
Rotatable Bonds 2
TPSA 60.36
LogP 0.16
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 12
Formal Charge -1
Fraction CSP3 0.0
Exact Mass 163.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Iochroma cyaneum Convolvulaceae Plantae 362357
2 Merremia dissecta Convolvulaceae Plantae 197414

Showing of synonyms

  • Sattar EA, Glasl H, et al. (1990). Hydroxycinnamic acid amides from Iochroma cyaneum. Phytochemistry,1990,29(12),3931-3933. [View]
Pubchem: 54729371
Chebi: 58152
Metabolights: MTBLC58152

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.04
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
42.62
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
5.75
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.1
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
1.17
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.14
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
1.43
Rat (Acute)
2.08
Rat (Chronic Oral)
2.43
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
311.32
Hydration Free Energy
-9.66
Log(D) at pH=7.4
-0.29
Log(P)
1.7
Log S
-1.94
Log(Vapor Pressure)
-4.61
Melting Point
204.04
pKa Acid
6.87
pKa Basic
4.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9464
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.9419
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9387
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9336
Threonine synthase 1, chloroplastic Q9S7B5 THRC1_ARATH Arabidopsis thaliana 3 0.9235
2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase Q988D3 Q988D3_RHILO Mesorhizobium japonicum) 3 0.9227
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9067
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8983
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8908
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8817
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.8713
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8680
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8500
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8353
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8322
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8296
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8253
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.8215
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8205
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8203
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.8141
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.8123
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8044
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7988
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7984
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7967
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7935
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7927
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7914
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7893
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7815
cAMP-activated global transcriptional regulator Vfr P55222 VFR_PSEAE Pseudomonas aeruginosa 3 0.7798
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7791
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7790
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7754
Precorrin-3 methylase O68097 O68097_RHOCA Rhodobacter capsulatus 3 0.7747
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7724
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7708
Mevalonate kinase P17256 KIME_RAT Rattus norvegicus 3 0.7696
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7692
5'-methylthioadenosine nucleosidase Q9T0I8 MTN1_ARATH Arabidopsis thaliana 3 0.7691
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 1 O88704 HCN1_MOUSE Mus musculus 3 0.7687
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7669
HD domain protein Q836G9 Q836G9_ENTFA Enterococcus faecalis 3 0.7642
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7636
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7619
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7588
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7585
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7549
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7543
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 Q9UL51 HCN2_HUMAN Homo sapiens 3 0.7539
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7530
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7523
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7517
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 3 0.7512
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7495
tRNA (cytidine-2'-O-)-methyltransferase TrmJ Q4JB16 TRMJ_SULAC Sulfolobus acidocaldarius 3 0.7473
Genome polyprotein Q8QL64 Q8QL64_9FLAV Modoc virus 3 0.7445
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7434
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7431
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7430
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7415
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7415
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7413
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7380
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7355
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7348
Ras-related protein Rap-1b P61224 RAP1B_HUMAN Homo sapiens 3 0.7344
Genome polyprotein A9LIE0 A9LIE0_9FLAV dengue virus type 3 3 0.7342
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7336
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7326
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7311
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7308
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7305
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7286
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7279
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7279
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7272
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7260
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7257
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7251
Genome polyprotein Q6YMS4 POLG_DEN3S Dengue virus type 3 3 0.7249
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7242
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7240
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7239
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7231
Petrobactin biosynthesis protein AsbB Q81RQ8 Q81RQ8_BACAN Bacillus anthracis 3 0.7226
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7220
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7218
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7215
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7208
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7204
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7192
histidine kinase Q9WZV7 Q9WZV7_THEMA Thermotoga maritima 3 0.7182
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7174
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7170
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7163
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7151
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7150
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7149
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7143
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7141
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7139
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 2 0.7132
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 2 0.7131
S-methyl-5'-thioadenosine phosphorylase I0B503 I0B503_SCHMA Schistosoma mansoni 3 0.7128
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7124
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7124
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7123
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7122
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7106
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7099
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7086
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7082
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7080
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7078
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7074
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7068
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7065
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 2 0.7060
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7056
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7054
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7054
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7053
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7051
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7051
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7048
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7045
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7043
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 2 0.7041
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7033
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7032
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7030
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7030
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7020
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7016
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7015
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7014

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