(2S,4R)-4,5,6,7-tetramethoxyflavan - Compound Card

(2S,4R)-4,5,6,7-tetramethoxyflavan

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(2S,4R)-4,5,6,7-tetramethoxyflavan

Structure
Zoomed Structure
  • Family: Lauraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavan
Canonical Smiles CO[C@@H]1C[C@H](Oc2c1c(OC)c(c(c2)OC)OC)c1ccccc1
InChI InChI=1S/C19H22O5/c1-20-14-10-13(12-8-6-5-7-9-12)24-15-11-16(21-2)18(22-3)19(23-4)17(14)15/h5-9,11,13-14H,10H2,1-4H3/t13-,14+/m0/s1
InChIKey IMKNBXLCVBCZGQ-UONOGXRCSA-N
Formula C19H22O5
HBA 5
HBD 0
MW 330.38
Rotatable Bonds 5
TPSA 46.15
LogP 3.92
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.37
Exact Mass 330.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Beilschmiedia zenkeri Lauraceae Plantae 88849

Showing of synonyms

  • Lenta BN, Tantangmo F, et al. (2009). Bioactive constituents of the stem bark of Beilschmiedia zenkeri.. Journal of natural products,2009, 72(12), 2130-2134. [View] [PubMed]
Pubchem: 44614520
Nmrshiftdb2: 60054291

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 210.28 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 134.18 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.370
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
78.61
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.400
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.620
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.300
Micronucleos
Safe
NR-AhR
Toxic
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
-1.250
Rat (Acute)
2.440
Rat (Chronic Oral)
1.780
Fathead Minnow
5.000
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
389.470
Hydration Free Energy
-6.840
Log(D) at pH=7.4
2.230
Log(P)
3.34
Log S
-3.4
Log(Vapor Pressure)
-5.96
Melting Point
86.8
pKa Acid
11.59
pKa Basic
1.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9693
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9505
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.9398
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9085
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9044
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9006
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8974
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8954
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8954
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8947
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8931
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8792
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.8732
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8702
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8695
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8614
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8612
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8604
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8564
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8545
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8533
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8533
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8491
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8479
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8407
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8395
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8391
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8351
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8329
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8310
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8304
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8250
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.8240
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8236
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8222
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8221
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8213
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8212
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8173
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8163
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8144
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8136
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.8092
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8088
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.8074
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8035
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8027
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8007
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7995
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7987
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7980
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7978
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7973
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7943
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7912
Beta-adrenergic receptor kinase 1 P25098 ARBK1_HUMAN Homo sapiens 3 0.7902
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7882
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7832
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7828
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7825
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7820
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7815
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7804
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7793
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7783
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7741
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7714
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7713
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7707
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7694
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7690
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7688
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7656
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7645
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7642
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7635
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7629
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7621
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7607
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7599
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7593
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7574
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7555
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7552
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7552
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7546
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7539
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7518
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7508
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7498
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7468
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7449
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7444
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7443
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7439
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7436
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7429
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7429
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7407
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7392
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7392
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7384
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 4 0.7367
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7364
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7362
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7360
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7355
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7351
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7344
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7337
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7336
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7327
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7326
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7325
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7321
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 2 0.7318
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7314
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7305
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7300
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7294
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7284
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7278
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7276
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7263
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7261
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7260
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7243
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7243
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7242
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7234
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7233
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7228
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7223
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7180
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7179
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7176
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7160
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7145
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7133
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7130
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7129
Quercetin 2,3-dioxygenase Q7SIC2 QDOI_ASPJA Aspergillus japonicus 3 0.7129
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7120
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7119
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7118
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7116
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7113
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7092
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7091
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7079
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7076
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7073
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7045
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7045
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7042
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7041
Poly [ADP-ribose] polymerase tankyrase-1 O95271 TNKS1_HUMAN Homo sapiens 2 0.7038
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7036
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7031
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7026
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7024
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7009
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 4 0.7008
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7004
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7001

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