Dihydrolophirone A - Compound Card

Dihydrolophirone A

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Dihydrolophirone A

Structure
Zoomed Structure
  • Family: Plantae - Ochnaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Biflavonoid
Canonical Smiles Oc1ccc(cc1)C([C@H](C1COc2c(C1=O)ccc(c2)O)C(=O)c1ccc(cc1O)O)c1ccc(cc1)O
InChI InChI=1S/C30H24O8/c31-18-5-1-16(2-6-18)27(17-3-7-19(32)8-4-17)28(30(37)22-11-9-20(33)13-25(22)35)24-15-38-26-14-21(34)10-12-23(26)29(24)36/h1-14,24,27-28,31-35H,15H2/t24?,28-/m0/s1
InChIKey NKQZNTIGVBMMBY-AZKKKJBWSA-N
Formula C30H24O8
HBA 8
HBD 5
MW 512.51
Rotatable Bonds 6
TPSA 144.52
LogP 4.74
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 512.15
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Lophira lanceolata Ochnaceae Plantae 670087

Showing of synonyms

  • Nkot JL, Ngono Bikobo DS, et al. (2018). Antitubercular evaluation of root extract and isolated phytochemicals from Lophira lanceolata against two resistant strains of Mycobacterium tuberculosis.. Pharmaceutical biology,2018, 56(1), 318-324. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)C(C(c2ccccc2)c3ccccc3)C(C4=O)COc(c45)cccc5

Level: 3

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1C(=O)C(Cc2ccccc2)C(C3=O)COc(c34)cccc4

Level: 2

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1C(c2ccccc2)CC(C3=O)COc(c34)cccc4

Level: 2

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1C(=O)CC(c2ccccc2)c3ccccc3

Level: 2

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1C(=O)CC(C2=O)COc(c23)cccc3

Level: 1

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1CCC(C2=O)COc(c23)cccc3

Level: 1

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1C(=O)CCc2ccccc2

Level: 1

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1Cc2ccccc2

Level: 1

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 512.51 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 512.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.93
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.970
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.410
Plasma Protein Binding
92.69
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
9.060
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.790
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.870
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
-1938.340
Rat (Acute)
2.270
Rat (Chronic Oral)
3.130
Fathead Minnow
12.640
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
576.680
Hydration Free Energy
-3.090
Log(D) at pH=7.4
3.380
Log(P)
3.44
Log S
-5.78
Log(Vapor Pressure)
-10.43
Melting Point
281.24
pKa Acid
7.11
pKa Basic
7.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9530
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9477
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9304
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9298
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9296
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9274
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.9267
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9241
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9196
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.9004
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8966
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8961
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.8854
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8845
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8781
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8757
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8712
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8705
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8656
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8628
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8565
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8532
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8524
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8497
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8470
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8470
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8466
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8367
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8361
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8358
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.8337
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.8299
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8271
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8263
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8257
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8234
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8204
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.8190
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8177
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8155
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8130
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.8066
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8035
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8018
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8011
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8001
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 4 0.7996
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7982
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7972
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7946
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7931
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 4 0.7907
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7860
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7858
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.7822
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7767
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7755
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7737
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7728
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7714
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7702
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7699
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 5 0.7694
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7650
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7649
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7637
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7634
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7624
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7621
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7617
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7599
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 3 0.7596
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7588
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7585
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7573
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7545
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7515
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7501
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7499
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7497
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7450
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7445
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7431
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7429
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7420
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7419
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7407
Polymerase basic protein 2 Q2LG68 Q2LG68_9INFA Influenza A virus) 4 0.7398
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7395
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7386
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7377
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7362
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7361
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7359
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7354
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7346
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7333
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7331
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7313
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7300
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7291
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 3 0.7266
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7258
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7250
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7250
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7249
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7249
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7245
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7242
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7236
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7234
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7231
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7228
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7223
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7221
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7210
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7203
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7184
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7179
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7173
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7166
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7150
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7143
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7142
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7132
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7119
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7118
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7109
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7109
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7108
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7107
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 5 0.7100
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7071
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7056
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7039
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7034
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 4 0.7022
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 4 0.7018
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7002
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7002

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