Isoarnottinin-4'-O-beta-D-glucoside - Compound Card

Isoarnottinin-4'-O-beta-D-glucoside

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Isoarnottinin-4'-O-beta-D-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Coumarin Glycoside
Canonical Smiles OC[C@H]1OC(OC/C(=C/Cc2c(O)ccc3c2oc(=O)cc3)/C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C20H24O9/c1-10(9-27-20-18(26)17(25)16(24)14(8-21)28-20)2-5-12-13(22)6-3-11-4-7-15(23)29-19(11)12/h2-4,6-7,14,16-18,20-22,24-26H,5,8-9H2,1H3/b10-2+/t14-,16-,17+,18-,20?/m1/s1
InChIKey SPZKLFHHFIWTLW-FTMSQIDYSA-N
Formula C20H24O9
HBA 9
HBD 5
MW 408.4
Rotatable Bonds 6
TPSA 149.82
LogP -0.2
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 408.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ammi majus Apiaceae Plantae 48026

Showing of synonyms

  • Elgamal MHA, Shalaby NMM, et al. (1993). Coumarins and coumarin glucosides from the fruits of Ammi majus. Phytochemistry,1993,34(3),819-823. [View]
Pubchem: 162944476

No compound-protein relationship available.

Structure

SMILES: c1cc(=O)oc(c12)c(ccc2)CC=CCOC3CCCCO3

Level: 1

Mol. Weight: 408.4 g/mol

Structure

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

Level: 0

Mol. Weight: 408.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 408.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
70.55
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
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
5.4
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.3
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.52
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.61
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
-14.65
Rat (Acute)
2.49
Rat (Chronic Oral)
3.17
Fathead Minnow
4.11
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
523.55
Hydration Free Energy
-10.37
Log(D) at pH=7.4
0.56
Log(P)
-0.49
Log S
-2.64
Log(Vapor Pressure)
-12.55
Melting Point
173.74
pKa Acid
5.35
pKa Basic
6.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9518
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9518
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.9036
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.9036
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8957
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8957
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8891
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8891
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8856
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8856
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8844
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8844
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8765
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8765
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8547
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8547
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8518
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8518
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8290
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8290
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8259
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8259
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8231
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8231
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8212
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8212
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8203
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8203
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8174
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8174
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8153
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8153
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8118
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8118
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7981
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7981
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7966
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7966
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7944
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7944
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7919
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7919
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7845
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7845
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7784
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7784
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7757
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7757
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7749
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7749
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7709
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7709
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7683
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7683
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7604
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7604
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7603
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7603
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7576
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7576
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7572
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7572
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7559
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7559
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7553
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7553
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7545
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7545
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7500
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7500
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7452
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7452
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7412
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7412
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7373
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7373
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7288
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7288
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7282
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7282
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7275
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7275
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7272
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7272
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7262
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7262
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7261
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7261
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7256
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7256
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7244
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7244
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7242
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7242
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7228
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7228
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 3 0.7215
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 3 0.7215
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7187
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7187
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7183
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7183
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7183
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7183
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7175
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7175
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7170
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7170
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7154
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7154
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7149
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7149
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7115
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7115
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7099
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7099
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7070
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7070
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7059
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7059
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7052
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7052
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7036
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7036
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7036
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7036
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7034
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7034
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7022
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7022
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7017
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7017
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7015
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7015
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7013
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7013
Glucosamine 6-phosphate N-acetyltransferase Q17427 GNA1_CAEEL Caenorhabditis elegans 3 0.7011
Glucosamine 6-phosphate N-acetyltransferase Q17427 GNA1_CAEEL Caenorhabditis elegans 3 0.7011
N-glycosylase/DNA lyase O15527 OGG1_HUMAN Homo sapiens 3 0.7005
N-glycosylase/DNA lyase O15527 OGG1_HUMAN Homo sapiens 3 0.7005
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7002
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7002
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7001
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7001

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