Petunidin-3-arabinoside - Compound Card

Petunidin-3-arabinoside

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Petunidin-3-arabinoside

Structure
Zoomed Structure
  • Family: Plantae - Lythraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Anthocyanin Glycoside
Canonical Smiles COc1cc(cc(c1O)O)c1[o+]c2cc(O)cc(c2cc1O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O.[Cl-]
InChI InChI=1S/C21H20O11.ClH/c1-29-15-3-8(2-12(24)17(15)26)20-16(32-21-19(28)18(27)13(25)7-30-21)6-10-11(23)4-9(22)5-14(10)31-20;/h2-6,13,18-19,21,25,27-28H,7H2,1H3,(H3-,22,23,24,26);1H/t13-,18-,19+,21-;/m0./s1
InChIKey DGLWRNZJQCODBU-IMBWBGPSSA-N
Formula C21H21ClO11
HBA 10
HBD 7
MW 484.84
Rotatable Bonds 4
TPSA 180.6
LogP -1.97
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 484.08
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Lagerstroemia indica Lythraceae Plantae 141186

Showing of synonyms

  • Saleh NAM (1973). Anthocyanins of Lagerstroemia indica flowers. Phytochemistry,1973,12(9),2304. [View]
CPRiL: 663
Structure

SMILES: c1cccc(c12)[o+]c(-c3ccccc3)c(c2)OC4CCCCO4

Level: 2

Mol. Weight: 484.84 g/mol

Structure

SMILES: c1cccc(c12)[o+]cc(c2)OC3CCCCO3

Level: 1

Mol. Weight: 484.84 g/mol

Structure

SMILES: c1cccc(c12)[o+]c(cc2)-c3ccccc3

Level: 1

Mol. Weight: 484.84 g/mol

Structure

SMILES: c1cc[o+]c(c12)cccc2

Level: 0

Mol. Weight: 484.84 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 484.84 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 484.84 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.540
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.890
Plasma Protein Binding
78.77
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
14.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.640
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.260
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.750
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
-71.660
Rat (Acute)
2.300
Rat (Chronic Oral)
3.850
Fathead Minnow
3.680
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
621.390
Hydration Free Energy
-5.400
Log(D) at pH=7.4
0.530
Log(P)
-1.71
Log S
-3.44
Log(Vapor Pressure)
-10.86
Melting Point
204.75
pKa Acid
4.38
pKa Basic
7.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9308
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9308
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9016
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.9016
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8956
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8956
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8853
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8853
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8788
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8788
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8776
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8776
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8662
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8662
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8629
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8629
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8627
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.8627
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8623
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8623
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8610
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8610
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8593
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8593
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8581
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8581
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8580
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8580
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8566
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8566
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8543
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8543
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8508
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8508
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8479
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8479
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.8472
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.8472
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8451
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8451
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8345
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8345
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8293
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8293
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8194
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8194
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8099
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8099
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8082
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8082
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8047
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8047
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7991
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7991
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7963
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7963
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7919
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7919
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7853
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7853
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7844
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7844
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7803
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7803
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7794
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7794
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7794
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7794
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7663
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7663
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7640
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7640
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7638
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7638
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7567
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7567
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7565
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7565
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7530
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7530
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7501
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7501
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7487
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7487
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7485
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7485
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7451
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7451
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7438
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7438
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7403
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7403
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7373
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7373
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7363
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7363
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7352
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7352
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7352
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7352
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7316
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7316
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7282
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7282
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7264
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7264
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7250
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7250
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7249
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7249
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7234
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7234
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 3 0.7223
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 3 0.7223
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7217
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7217
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7217
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7217
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7212
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7212
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7210
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7210
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7208
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7208
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7200
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7200
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7192
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7192
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7139
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7139
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7128
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7128
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7122
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7122
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7114
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7114
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7085
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7085
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7054
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7054
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7027
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7027
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7026
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7026
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7013
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7013
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7011
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7011

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