Liquiritigeninyl-(1-3,II-3)-naringenin - Compound Card

Liquiritigeninyl-(1-3,II-3)-naringenin

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Liquiritigeninyl-(1-3,II-3)-naringenin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Biflavanone
Canonical Smiles Oc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1[C@@H]1[C@H](Oc2c(C1=O)ccc(c2)O)c1ccc(cc1)O)O
InChI InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)29-25(27(36)20-10-9-18(33)12-22(20)38-29)26-28(37)24-21(35)11-19(34)13-23(24)39-30(26)15-3-7-17(32)8-4-15/h1-13,25-26,29-35H/t25-,26-,29+,30+/m0/s1
InChIKey MFXZKXGEIZZQJC-SRPPIYJJSA-N
Formula C30H22O9
HBA 9
HBD 5
MW 526.5
Rotatable Bonds 3
TPSA 153.75
LogP 4.78
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 526.13
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ochna holstii Ochnaceae Plantae 1389766
2 Ormocarpum sennoides Leguminosae/Fabaceae Plantae 77289

Showing of synonyms

  • Kalenga TM, Ndoile MM, et al. (2021). Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii. Journal of natural products,2021, 84(2), 364-372. [View] [PubMed]
  • Chalo DM, Kakudidi E, et al. (2021). Chemical constituents of the roots of Ormocarpum sennoides subsp. Zanzibaricum. Biochemical Systematics and Ecology, 2021, 97,104277. [View]
Pubchem: 46222775
Nmrshiftdb2: 70039500

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 526.5 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 526.5 g/mol

Structure

SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 526.5 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 526.5 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 526.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 526.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.91
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.910
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.370
Plasma Protein Binding
95.83
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
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.520
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.500
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.970
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.220
Micronucleos
Toxic
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
-3770.080
Rat (Acute)
2.290
Rat (Chronic Oral)
3.270
Fathead Minnow
17.320
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
567.930
Hydration Free Energy
-3.050
Log(D) at pH=7.4
3.620
Log(P)
4.07
Log S
-6.52
Log(Vapor Pressure)
-9.89
Melting Point
340.36
pKa Acid
7.87
pKa Basic
5.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9615
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9277
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.9015
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8961
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8932
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8834
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8783
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8780
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8749
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8555
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8547
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8471
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8463
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8451
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8431
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8422
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8363
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.8362
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8342
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8340
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8307
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8287
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8266
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8109
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8067
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.8004
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7961
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7921
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7920
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7881
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7876
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7875
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7863
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7837
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7827
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7824
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7803
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7777
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7772
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7751
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7743
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7741
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7728
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7695
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7679
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7643
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7597
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 3 0.7525
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7503
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7497
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7493
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7480
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7472
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7469
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7469
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7439
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7423
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7395
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7377
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7368
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7358
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7354
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7346
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7328
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7321
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7317
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7305
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7294
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7276
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7275
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7266
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7265
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 4 0.7255
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7220
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7204
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7195
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7178
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7164
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7148
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7147
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7136
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7133
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7131
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7122
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 5 0.7116
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7107
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7097
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7094
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7022
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7017

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