Stearyl-p-coumarate [octadecanyl 3- (4-hydroxyphenyl)prop-2-enoate] - Compound Card

Stearyl-p-coumarate [octadecanyl 3- (4-hydroxyphenyl)prop-2-enoate]

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Stearyl-p-coumarate [octadecanyl 3- (4-hydroxyphenyl)prop-2-enoate]

Structure
Zoomed Structure
  • Family: Plantae - Mimosaceae
  • Kingdom: Plantae
  • Class: Phenylpropanoid
    • Subclass: Phenylpropanoid Derivative
Canonical Smiles CCCCCCCCCCCCCCCCCCOC(=O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C27H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24-30-27(29)23-20-25-18-21-26(28)22-19-25/h18-23,28H,2-17,24H2,1H3/b23-20+
InChIKey SXXOKKBSVARFFB-BSYVCWPDSA-N
Formula C27H44O3
HBA 3
HBD 1
MW 416.65
Rotatable Bonds 19
TPSA 46.53
LogP 8.21
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 416.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Dorstenia psilurus Mimosaceae Plantae 106723

Showing of synonyms

  • Ngadjui BT, Dongo E, et al. (1998). Prenylated flavones and phenylpropanoid derivatives from roots of Dorstenia psilurus. Phytochemistry, 1998, 48(4), 733-737. [View]
Pubchem: 12018904
Chebi: 191987
Nmrshiftdb2: 60073726

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 416.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.78
Plasma Protein Binding
47.47
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
3.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.27
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.47
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.29
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-13.08
Rat (Acute)
1.57
Rat (Chronic Oral)
2.57
Fathead Minnow
4.63
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
451.47
Hydration Free Energy
-3.42
Log(D) at pH=7.4
6.65
Log(P)
10.8
Log S
-6.14
Log(Vapor Pressure)
-8.13
Melting Point
65.71
pKa Acid
10.42
pKa Basic
5.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9720
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9379
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9362
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9355
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9189
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9007
S-methyl-5'-thioadenosine phosphorylase I0B503 I0B503_SCHMA Schistosoma mansoni 3 0.8702
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 3 0.8587
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8547
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8325
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8296
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8175
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7752
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7729
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7687
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 2 0.7684
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7627
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 2 0.7605
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7562
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 2 0.7548
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7529
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7514
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7492
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7491
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7476
S-methyl-5'-thioadenosine phosphorylase Q97W94 MTAP_SACS2 Saccharolobus solfataricus 3 0.7464
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7455
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7449
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7445
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7443
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7420
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7418
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7408
S-methyl-5'-thioadenosine phosphorylase Q13126 MTAP_HUMAN Homo sapiens 3 0.7402
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7402
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7401
S-methyl-5'-thioadenosine phosphorylase Q13126 MTAP_HUMAN Homo sapiens 3 0.7392
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7385
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7379
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7348
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7347
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 2 0.7338
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7335
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7329
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7322
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7320
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 2 0.7303
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7299
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7296
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 2 0.7289
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7286
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7278
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7274
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7271
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7270
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7263
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7261
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7259
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7257
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7257
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7257
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7251
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7245
L-seryl-tRNA(Sec) kinase Q58933 PSTK_METJA Methanocaldococcus jannaschii 2 0.7244
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7233
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7226
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7223
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7222
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7220
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7217
Nucleoside diphosphate kinase A5J299 A5J299_PENVA Penaeus vannamei 2 0.7213
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7211
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7211
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7209
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7209
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7208
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7207
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7199
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7197
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7195
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7193
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7191
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7174
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7169
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7168
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7165
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7161
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7161
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7158
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7157
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 2 0.7154
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 2 0.7153
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7153
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7150
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7150
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7150
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7145
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7144
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7138
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7135
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 2 0.7118
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7115
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7107
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7104
S-methyl-5'-thioadenosine phosphorylase Q97W94 MTAP_SACS2 Saccharolobus solfataricus 3 0.7101
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7099
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 2 0.7096
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7094
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7091
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7087
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7086
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 2 0.7086
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7081
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7075
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7073
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 2 0.7071
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7063
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7063
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7056
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7054
cAMP-activated global transcriptional regulator Vfr P55222 VFR_PSEAE Pseudomonas aeruginosa 3 0.7045
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7045
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7042
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7029
Nucleoside diphosphate kinase Q2SWE7 NDK_BURTA Burkholderia thailandensis 2 0.7027
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7026
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7024
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7022
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7018
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7015
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7014
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7014
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7010
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7005
Uncharacterized ACR, COG1565 superfamily Q2T1U7 Q2T1U7_BURTA Burkholderia thailandensis 2 0.7002
Coniferyl alcohol 9-O-methyltransferase A6XNE6 A6XNE6_9ROSI Linum nodiflorum 2 0.7001

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