Neohesperidin - Compound Card

Neohesperidin

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Neohesperidin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2cc3O[C@@H](CC(=O)c3c(c2)O)c2ccc(c(c2)O)OC)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
InChIKey ARGKVCXINMKCAZ-UZRWAPQLSA-N
Formula C28H34O15
HBA 15
HBD 8
MW 610.57
Rotatable Bonds 7
TPSA 234.29
LogP -1.16
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 610.19
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Senecio angulatus Asteraceae Plantae 189229

Showing of synonyms

  • Bousetla A, Keskinkaya H.B, et al. (2023). LC-ESI/MS-phytochemical profiling with antioxidant and antiacetylcholinesterase activities of Algerian Senecio angulatus L.f. extracts. Natural product research, 2023, 37(1), 123-129. [View] [PubMed]
Pubchem: 442439
Kegg Ligand: C09806
Chebi: 59016
Nmrshiftdb2: 60023886
Metabolights: MTBLC59016
CPRiL: 56731
Structure

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 610.57 g/mol

Structure

SMILES: O=C1CCOc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 610.57 g/mol

Structure

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 610.57 g/mol

Structure

SMILES: O=C1CCOc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 610.57 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 610.57 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 610.57 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 610.57 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 610.57 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 610.57 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.050
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
8.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.790
Plasma Protein Binding
70.9
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
8.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.310
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.580
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.140
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
-15358.330
Rat (Acute)
2.420
Rat (Chronic Oral)
4.450
Fathead Minnow
33.660
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
390.130
Hydration Free Energy
-2.920
Log(D) at pH=7.4
0.510
Log(P)
-0.17
Log S
-4.64
Log(Vapor Pressure)
-14.99
Melting Point
195.63
pKa Acid
4.23
pKa Basic
3.43
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 0.9497
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9495
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9469
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9464
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9164
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9023
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8926
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8832
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8773
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8737
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8701
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8404
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8325
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8324
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8154
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8099
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8094
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8073
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8033
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7992
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7983
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7941
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7933
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7911
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7848
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7804
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7799
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7790
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7788
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7782
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7645
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7642
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7637
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7606
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7602
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7594
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7584
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7563
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7545
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7540
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7523
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7511
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7499
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7476
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7471
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7466
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7455
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7447
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7434
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7419
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7416
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7402
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7384
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7383
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7380
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7370
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7358
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7331
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7326
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7304
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7285
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7284
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7283
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7269
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7264
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7259
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7247
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7242
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7220
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7211
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7209
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7200
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7194
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7185
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7185
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7185
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7154
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7136
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7136
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7136
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7124
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7121
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7113
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7112
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7108
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7104
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7100
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7096
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7089
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7078
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7067
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7065
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7059
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7058
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7057
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7056
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7052
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7050
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7047
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7046
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7046
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7039
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7024
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7016
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7013
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7008

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