4-hydroxylonchocarpin - Compound Card

4-hydroxylonchocarpin

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4-hydroxylonchocarpin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Chalcone Derivative
Canonical Smiles Oc1ccc(cc1)/C=C/C(=O)c1ccc2c(c1O)C=CC(O2)(C)C
InChI InChI=1S/C20H18O4/c1-20(2)12-11-16-18(24-20)10-8-15(19(16)23)17(22)9-5-13-3-6-14(21)7-4-13/h3-12,21,23H,1-2H3/b9-5+
InChIKey IQHPDUUSMBMDGN-WEVVVXLNSA-N
Formula C20H18O4
HBA 4
HBD 2
MW 322.36
Rotatable Bonds 3
TPSA 66.76
LogP 4.18
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 322.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Millettia dura Leguminosae/Fabaceae Plantae 62119
2 Dorstenia dinklagei Moraceae Plantae 2604986
3 Dorstenia mannii Moraceae Plantae 194258
4 Dorstenia poinsettiifolia Moraceae Plantae 2605000

Showing of synonyms

  • Ngadjui BT, Dongo E, et al. (2002). Dinklagins A, B and C: three prenylated flavonoids and other constituents from the twigs of Dorstenia dinklagei.. Phytochemistry,2002, 61(1), 99-104. [View] [PubMed]
  • Buyinza D, Chalo DM, et al. (2020). Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values. Biochemical Systematics and Ecology, 2020, 91, 104053. [View]
  • Ngadjui BT, Kapche GW, et al. (1999). Prenylated flavonoids and a dihydro-4-phenylcoumarinfrom Dorstenia poinsettifolia. Phytochemistry, 1999, 51(1), 119-123. [View]
  • Ngadjui BT, Kouam SF, et al. (2000). Prenylated flavonoids from the aerial parts of Dorstenia mannii.. Phytochemistry,2000, 55(8), 915-919. [View] [PubMed]
CPRiL: 212293
Structure

SMILES: C1=CCOc(c12)ccc(c2)C(=O)C=Cc3ccccc3

Level: 1

Mol. Weight: 322.36 g/mol

Structure

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 322.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 322.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.010
Plasma Protein Binding
52.39
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.940
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.490
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.230
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.060
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.150
Rat (Acute)
2.260
Rat (Chronic Oral)
2.560
Fathead Minnow
4.810
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
438.200
Hydration Free Energy
-10.680
Log(D) at pH=7.4
4.310
Log(P)
4.84
Log S
-5.54
Log(Vapor Pressure)
-7.87
Melting Point
173.8
pKa Acid
7.93
pKa Basic
4.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9449
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.9339
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9250
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9084
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9014
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8543
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8360
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8345
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8340
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 4 0.8328
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8323
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8285
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.8258
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.8207
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.8141
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8080
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7981
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7931
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7922
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7892
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7850
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7811
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7786
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7769
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7735
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7727
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7716
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7707
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7689
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7669
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7659
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7649
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7648
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7630
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7613
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7597
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7583
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7581
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7566
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7554
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7550
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7540
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7525
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7516
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7496
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7486
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7470
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7460
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7456
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7455
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7444
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7437
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7422
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7422
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7399
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.7386
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7385
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7382
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7380
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7379
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7363
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7363
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7359
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7354
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7352
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7350
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7349
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7313
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7307
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7282
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7280
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7275
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7274
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7273
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7268
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7249
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7242
Subunit alpha of sarocosine oxidase Q50LF0 Q50LF0_9CORY Corynebacterium sp. U-96 4 0.7239
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7237
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7229
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7218
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7213
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7211
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7211
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7209
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7202
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7200
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7186
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7181
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7179
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7178
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7176
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7174
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7174
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7146
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7138
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7133
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7133
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7126
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7122
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7115
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7115
Retinoic acid receptor gamma P13631 RARG_HUMAN Homo sapiens 3 0.7108
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7106
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7093
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7092
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7085
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7082
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7082
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7060
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 3 0.7055
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7051
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7049
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7045
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7041
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 3 0.7041
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7027
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7026
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7019
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7018
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7015
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7014
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7006
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7005

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