3,4'-dihydroxy-3'-methoxypropiophenone - Compound Card

3,4'-dihydroxy-3'-methoxypropiophenone

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3,4'-dihydroxy-3'-methoxypropiophenone

Structure
Zoomed Structure
  • Family: Cucurbitaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Propiophenone
Canonical Smiles OCCC(=O)c1cc(OC)c(c(c1)OC)O
InChI InChI=1S/C11H14O5/c1-15-9-5-7(8(13)3-4-12)6-10(16-2)11(9)14/h5-6,12,14H,3-4H2,1-2H3
InChIKey UHOAHNLBCNGCHE-UHFFFAOYSA-N
Formula C11H14O5
HBA 5
HBD 2
MW 226.23
Rotatable Bonds 5
TPSA 75.99
LogP 0.97
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 226.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrullus colocynthis Cucurbitaceae Plantae 252529

Showing of synonyms

  • Yoshikawa M, Morikawa T, et al. (2007). Bioactive Saponins and Glycosides. XXVII. 1) Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis. Chemical & pharmaceutical bulletin, 2007, 55(3), 428-34. [View] [PubMed]
Pubchem: 54353627
Nmrshiftdb2: 60070067

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.37
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.240
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.500
Plasma Protein Binding
16.08
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
8.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.660
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.160
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.170
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
2.910
Rat (Acute)
1.960
Rat (Chronic Oral)
2.620
Fathead Minnow
3.960
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
328.570
Hydration Free Energy
-10.240
Log(D) at pH=7.4
0.480
Log(P)
0.34
Log S
-1.61
Log(Vapor Pressure)
-4.68
Melting Point
112.28
pKa Acid
7.43
pKa Basic
3.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9715
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9623
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9497
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9488
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9278
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9161
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9133
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9119
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9092
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9071
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9062
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9039
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9029
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9015
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9012
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8875
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8831
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8761
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.8757
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8742
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8730
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8716
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8708
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8648
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8641
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8609
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8603
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8499
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8429
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.8388
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8384
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8381
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8349
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8344
Coniferyl alcohol 9-O-methyltransferase A6XNE6 A6XNE6_9ROSI Linum nodiflorum 3 0.8326
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8298
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8254
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8242
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8241
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8241
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.8178
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 4 0.8165
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.8152
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8132
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.8113
Beta-galactoside alpha-2,6-sialyltransferase 1 P15907 SIAT1_HUMAN Homo sapiens 4 0.8102
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8086
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.8040
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8020
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8010
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8010
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7943
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7941
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7902
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 4 0.7896
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7874
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7871
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 4 0.7858
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7833
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7829
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7793
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 4 0.7782
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7782
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7723
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7675
Adenosine receptor A2a P29274 AA2AR_HUMAN Homo sapiens 4 0.7666
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7665
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7658
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7656
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7652
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7624
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7622
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.7597
Spermidine synthase P19623 SPEE_HUMAN Homo sapiens 4 0.7596
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7583
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7580
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7572
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7563
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 4 0.7550
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7545
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7532
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7531
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7522
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7512
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7483
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7481
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7478
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 4 0.7477
Uroporphyrinogen-III C-methyltransferase P21631 SUMT_SINSX Sinorhizobium sp 4 0.7452
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7449
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7437
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7435
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7424
Adenylosuccinate synthetase isozyme 1 P28650 PURA1_MOUSE Mus musculus 4 0.7420
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7402
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7401
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7397
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7391
Diphthine synthase O58456 DPHB_PYRHO Pyrococcus horikoshii 4 0.7361
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7359
(6-4) photolyase A9CH39 PHRB_AGRFC Agrobacterium fabrum) 5 0.7334
GTPase KRas P01116 RASK_HUMAN Homo sapiens 4 0.7321
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7313
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7297
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7289
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7286
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7277
tRNA (guanine-N(1)-)-methyltransferase Q2GIL5 TRMD_ANAPZ Anaplasma phagocytophilum 4 0.7269
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7265
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7260
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 3 0.7259
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7247
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7243
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7232
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7230
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7226
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7224
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7218
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7218
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7214
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7207
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7202
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7201
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7180
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7179
Release factor glutamine methyltransferase Q9WYV8 PRMC_THEMA Thermotoga maritima 3 0.7172
Purine phosphoribosyltransferase (GpT-1) Q97W95 Q97W95_SACS2 Saccharolobus solfataricus 3 0.7156
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7149
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7148
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7144
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7144
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 3 0.7142
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7138
N-acetylhexosamine 1-kinase E8MF12 NAHK_BIFL2 Bifidobacterium longum subsp. longum 3 0.7129
Ras-related protein Rab-3 P25228 RAB3_DROME Drosophila melanogaster 4 0.7126
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7121
ADP-ribosylation factor-like protein 3 A8ISN6 ARL3_CHLRE Chlamydomonas reinhardtii 4 0.7110
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7107
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7094
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7092
dCTP deaminase, dUMP-forming Q9KFV3 DCDB_BACHD Halalkalibacterium halodurans 5 0.7082
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7082
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7078
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7070
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 3 0.7065
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7057
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7056
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7054
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7053
DNA (cytosine-5)-methyltransferase 1 Q9AXT8 H32_ARATH Zea mays 3 0.7044
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 3 0.7044
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7043
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7031
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7025
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7024
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7023
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7021
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7019
ADP-ribosylation factor 1 P11076 ARF1_YEAST Saccharomyces cerevisiae 4 0.7017
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7015
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7009
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7007
Ribosomal RNA small subunit methyltransferase Nep1 Q57977 NEP1_METJA Methanocaldococcus jannaschii 4 0.7001

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