Azaleatin 3-rhamnoside - Compound Card

Azaleatin 3-rhamnoside

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Azaleatin 3-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Juglandaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles COc1cc(O)cc2c1c(=O)c(c(o2)c1ccc(c(c1)O)O)O[C@@H]1OC(C)[C@@H](C([C@@H]1O)O)O
InChI InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-13(30-2)6-10(23)7-14(15)32-20(21)9-3-4-11(24)12(25)5-9/h3-8,16,18-19,22-26,28-29H,1-2H3/t8?,16-,18?,19-,22-/m0/s1
InChIKey FYSMTINDJSASRR-BDOJHUBJSA-N
Formula C22H22O11
HBA 11
HBD 6
MW 462.41
Rotatable Bonds 4
TPSA 179.28
LogP 0.79
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 462.12
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Curya pecan Juglandaceae Plantae 32201

Showing of synonyms

  • Ishak MS, Ahmed AA, et al. (1980). Flavonol glycosides of Carya pecan. Phytochemistry,1980,19,2512-2513. [View]
Pubchem: 44259531
Nmrshiftdb2: 60114733

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 462.41 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 462.41 g/mol

Structure

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

Level: 1

Mol. Weight: 462.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.88
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.240
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.960
Plasma Protein Binding
76.42
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
14.890
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.840
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-108.680
Rat (Acute)
2.320
Rat (Chronic Oral)
3.760
Fathead Minnow
4.190
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
605.050
Hydration Free Energy
-4.050
Log(D) at pH=7.4
0.750
Log(P)
0.9
Log S
-4.33
Log(Vapor Pressure)
-10.77
Melting Point
211.2
pKa Acid
5.93
pKa Basic
5.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9338
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9338
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9018
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9018
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 8 0.8963
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 8 0.8963
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8933
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8933
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8910
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8910
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8906
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8906
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8792
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8792
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8785
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8785
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8730
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8730
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8713
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8713
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8695
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8695
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8685
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8685
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8655
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8655
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8476
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8476
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8474
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8474
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8432
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8432
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8356
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8356
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8336
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8336
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8304
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8304
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8291
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8291
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8247
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8247
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8235
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8235
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8233
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8233
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8229
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8229
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8180
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8180
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8172
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8172
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8170
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8170
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8144
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8144
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8139
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8139
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8111
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8111
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8082
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8082
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.8078
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.8078
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8073
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8073
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8042
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8042
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8016
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8016
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7938
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7938
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7876
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7876
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7855
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7855
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7851
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7851
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7814
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7814
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7801
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7801
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7725
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7725
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7716
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7716
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7714
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7714
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7662
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7662
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7652
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7652
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7633
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7633
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7630
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7630
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7535
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7535
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7533
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7533
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7529
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 6 0.7529
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7491
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7491
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7463
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7463
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7453
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7453
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7395
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7395
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7340
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7340
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7320
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7320
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7312
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7312
Primosomal protein N' A6TGC5 A6TGC5_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7290
Primosomal protein N' A6TGC5 A6TGC5_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7290
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7193
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7193
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7171
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7171
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7166
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7166
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7160
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7160
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7158
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7158
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7132
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7132
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7101
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7101
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7100
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7100
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7089
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7089
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7087
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7087
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7071
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7071
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7059
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7059
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7034
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7034

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