Lanaroflavone - Compound Card

Lanaroflavone

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Lanaroflavone

Structure
Zoomed Structure
  • Family: Plantae - Iridaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles Oc1ccc(cc1)c1cc(=O)c2c(o1)c(Oc1ccc(cc1)c1cc(=O)c3c(o1)cc(cc3O)O)c(cc2O)O
InChI InChI=1S/C30H18O10/c31-16-5-1-14(2-6-16)25-13-22(36)28-20(34)11-23(37)29(30(28)40-25)38-18-7-3-15(4-8-18)24-12-21(35)27-19(33)9-17(32)10-26(27)39-24/h1-13,31-34,37H
InChIKey DLWAHHFLQNUOIA-UHFFFAOYSA-N
Formula C30H18O10
HBA 10
HBD 5
MW 538.46
Rotatable Bonds 4
TPSA 170.8
LogP 5.55
Number Rings 6
Number Aromatic Rings 6
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 538.09
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Dietes bicolor Iridaceae Plantae 93015

Showing of synonyms

  • Ayoub I.M, Korinek M, et al. (2018). Probing the antiallergic and anti-inflammatory activity of biflavonoids and dihydroflavonols from dietes bicolor. Journal of natural products, 2018, 81(2), 243-253. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)Oc(cc4)ccc4-c(cc5=O)oc(c56)cccc6

Level: 3

Mol. Weight: 538.46 g/mol

Structure

SMILES: O=c1ccoc(c12)c(ccc2)Oc(cc3)ccc3-c(cc4=O)oc(c45)cccc5

Level: 2

Mol. Weight: 538.46 g/mol

Structure

SMILES: c1ccccc1Oc(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 538.46 g/mol

Structure

SMILES: O=c1ccoc(c12)c(ccc2)Oc3ccccc3

Level: 1

Mol. Weight: 538.46 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 538.46 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 538.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 538.46 g/mol

Anti-inflammatory
Antiallergic

Absorption

Caco-2 (logPapp)
-5.89
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.030
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
4.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.610
Plasma Protein Binding
99.77
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.320
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.470
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.420
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.900
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-5874.250
Rat (Acute)
2.450
Rat (Chronic Oral)
2.790
Fathead Minnow
20.580
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
609.610
Hydration Free Energy
-3.040
Log(D) at pH=7.4
4.080
Log(P)
5.86
Log S
-7.61
Log(Vapor Pressure)
-9.61
Melting Point
431.91
pKa Acid
9.99
pKa Basic
4.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9761
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9485
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9280
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9265
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.9252
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9217
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.9147
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.9124
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.9105
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9076
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9003
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8980
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8969
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8916
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8845
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8841
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8809
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8791
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8789
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8763
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8737
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8696
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8673
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8664
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8569
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8503
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8499
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8489
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8449
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8447
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8411
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8394
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8347
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8318
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8303
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.8280
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8275
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8273
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8267
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8255
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8239
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8222
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8198
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8192
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8179
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8170
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8102
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8082
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.8054
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8046
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8042
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8042
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8037
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8002
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7988
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7987
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7955
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7934
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7917
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7895
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7892
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7890
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7839
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7835
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7832
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7821
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7779
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7778
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7761
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 3 0.7756
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7738
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7727
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7711
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7705
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7705
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7690
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7687
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7687
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7675
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7672
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7662
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7661
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7613
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7591
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7582
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7574
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7554
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7547
Bromodomain-containing protein 9 Q9H8M2 BRD9_HUMAN Homo sapiens 3 0.7545
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7537
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7535
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7535
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7525
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7489
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7482
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7470
Renin P00797 RENI_HUMAN Homo sapiens 4 0.7463
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7462
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7456
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7453
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7451
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7436
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7419
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7414
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7388
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7386
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7382
RAC-alpha serine/threonine-protein kinase P31749 AKT1_HUMAN Homo sapiens 3 0.7381
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7378
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7372
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7372
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7362
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7352
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7352
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7345
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7332
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7322
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7321
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7316
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7313
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7306
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7298
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7292
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7288
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7282
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7268
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7268
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7256
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7246
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7230
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7222
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7210
Tissue factor P13726 TF_HUMAN Homo sapiens 3 0.7208
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7207
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 4 0.7197
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7184
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.7178
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7174
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7172
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7171
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7166
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7163
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7119
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7100
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7094
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7092
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7078
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7076
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7064
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7057
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7048
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7045
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7029
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.7028
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7025
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.7017
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7015
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7015
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7014

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