Atraflavoside A - Compound Card

Atraflavoside A

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Atraflavoside A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles COc1c(O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O)O)O)cc2c(c1O)c(=O)c(c(o2)c1ccc(cc1)O)O
InChI InChI=1S/C22H20O13/c1-32-19-10(34-22-17(29)14(26)16(28)20(35-22)21(30)31)6-9-11(13(19)25)12(24)15(27)18(33-9)7-2-4-8(23)5-3-7/h2-6,14,16-17,20,22-23,25-29H,1H3,(H,30,31)/t14-,16-,17+,20-,22+/m0/s1
InChIKey UCYWIDLIMBHGLZ-UCPBUJGOSA-N
Formula C22H20O13
HBA 12
HBD 7
MW 492.39
Rotatable Bonds 5
TPSA 216.58
LogP -0.14
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 492.09
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Atractylis flava Asteraceae Plantae 41483

Showing of synonyms

  • Chabani S, Haba H, et al. (2013). Flavonoid glycosides and triterpenoids from Atractylis flava.. Phytochemistry Letters,2013,6,9-13. [View]
Pubchem: 102202098
Nmrshiftdb2: 60066923

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 492.39 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 492.39 g/mol

Structure

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

Level: 1

Mol. Weight: 492.39 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 492.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 492.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 492.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.360
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
84.9
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
7.650
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.910
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.940
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.720
Micronucleos
Toxic
NR-AhR
Safe
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
-271.290
Rat (Acute)
2.260
Rat (Chronic Oral)
4.250
Fathead Minnow
3.850
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
608.810
Hydration Free Energy
-3.820
Log(D) at pH=7.4
-0.970
Log(P)
0.04
Log S
-4.27
Log(Vapor Pressure)
-12.89
Melting Point
220.43
pKa Acid
4.62
pKa Basic
5.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9539
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9539
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9174
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9174
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9168
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9168
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8940
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8940
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8890
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8890
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8711
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8711
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8698
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8698
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8514
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8514
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8399
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8399
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8352
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8352
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8333
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8333
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8295
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8295
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8243
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8243
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8210
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8210
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 5 0.8195
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 5 0.8195
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8139
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8139
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8088
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8088
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8036
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8036
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.8019
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.8019
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.8013
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.8013
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8012
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8012
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7924
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7924
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7896
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7896
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.7796
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.7796
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7796
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7796
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7784
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7784
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7728
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7728
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7711
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7711
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7706
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7706
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7675
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7675
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7638
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7638
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7619
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7619
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7615
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7615
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7596
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7596
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7589
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7589
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7568
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 5 0.7568
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7551
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7551
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7541
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7541
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7534
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7534
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7515
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7515
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7508
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7508
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 5 0.7507
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 5 0.7507
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7500
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7500
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7491
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7491
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7451
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7451
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7448
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7448
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7399
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7399
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7393
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7393
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7369
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7369
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7360
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7360
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7352
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7352
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7280
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7280
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7278
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7278
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7270
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7270
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7263
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7263
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7212
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7212
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7206
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7206
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7198
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7198
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7198
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7198
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7196
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7196
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 4 0.7190
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 4 0.7190
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7184
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7184
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7167
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7167
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7159
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7159
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7149
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7149
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7147
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7147
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7135
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7135
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7116
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7116
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7115
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7115
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7112
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7112
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7112
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7112
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7079
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7079
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7072
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7072
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7068
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7068
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7056
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7056
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7052
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7052
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7047
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7047
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7046
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7046
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7045
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7045
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7030
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7030

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