Isoacteoside - Compound Card

Isoacteoside

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Isoacteoside

Structure
Zoomed Structure
  • Family: Plantae - Globulariaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles O=C(OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
InChIKey FNMHEHXNBNCPCI-QEOJJFGVSA-N
Formula C29H36O15
HBA 15
HBD 9
MW 624.59
Rotatable Bonds 10
TPSA 245.29
LogP -1.02
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 624.21
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Ruellia patula Acanthaceae Plantae 441006
2 Jacaranda mimosaefolia Bignoniaceae Plantae 185774
3 Tecoma mollis Bignoniaceae Plantae 2822953
4 Amphilophium paniculatum Bignoniaceae Plantae 353927
5 Globularia alypum Globulariaceae Plantae 1533088

Showing of synonyms

  • Samy MN, Khalil HE, et al. (2015). Amphipaniculosides A-D, triterpenoid glycosides, and amphipaniculoside E, an aliphatic alcohol glycoside from the leaves of Amphilophium paniculatum. Phytochemistry,2015,115,261-268. [View] [PubMed]
  • Es-Safi NE, Khlifi S, et al. (2005). Antioxidant constituents of the aerial parts of Globularia alypum growing in Morocco. Journal of Natural Products,2005,68,1293-1296. [View] [PubMed]
  • Abdel-Mageed WM, Backheet EY, et al. (2012). Antiparasitic antioxidant phenylpropanoids and iridoid glycosides from Tecoma mollis. Fitoterapia,2012,83(3),500-507. [View] [PubMed]
  • Zaghloul AM, Gohar AA, et al. (2011). Phenylpropanoids from the stem bark of Jacaranda mimosaefolia. Natural Product Research,2011,25(1),68-76. [View] [PubMed]
  • Samy MN, Khalil HE, et al. (2011). Three new flavonoid glycosides, byzantionoside B 6’-O-Sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula. Chemical and Pharmaceutical Bulletin,2011,59(6),725-729. [View] [PubMed]
CPRiL: 75388
Structure

SMILES: c1ccccc1C=CC(=O)OCC2CC(OC3CCCCO3)CC(O2)OCCc4ccccc4

Level: 3

Mol. Weight: 624.59 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OCCc3ccccc3

Level: 2

Mol. Weight: 624.59 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CC(CCO2)OC3CCCCO3

Level: 2

Mol. Weight: 624.59 g/mol

Structure

SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 624.59 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 624.59 g/mol

Structure

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 624.59 g/mol

Structure

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 624.59 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 624.59 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 624.59 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.91
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.11
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
10.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
67.42
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
11.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.14
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.3
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
-18879.33
Rat (Acute)
2.14
Rat (Chronic Oral)
4.43
Fathead Minnow
40.86
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
351.03
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.27
Log(P)
0.27
Log S
-4.07
Log(Vapor Pressure)
-15.88
Melting Point
201.63
pKa Acid
5.07
pKa Basic
5.33
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 0.9356
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9356
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9151
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9151
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8818
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8818
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8781
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8781
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8680
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8680
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8665
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8665
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8536
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8536
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8487
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8487
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8342
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8342
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8339
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8339
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8295
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8295
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8273
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8273
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8072
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8072
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7988
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7988
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7973
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7973
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7964
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7964
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7945
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7945
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7909
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7909
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7773
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7773
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7768
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7768
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7623
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7623
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7621
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7621
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7569
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7569
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7538
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7538
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7529
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7529
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7518
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7518
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7509
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7509
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7494
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7494
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7471
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7471
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7468
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7468
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7435
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7435
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7382
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7382
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7368
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7368
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7366
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7366
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7337
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7337
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7271
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7271
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7252
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7252
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7213
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7213
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7191
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7191
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7191
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7191
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7160
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7160
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7147
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7147
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7131
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7131
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7118
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7118
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7109
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7109
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7090
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7090
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7071
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7071
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7045
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7045
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7038
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7038
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7031
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7031
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7030
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7030
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7029
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7029
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7023
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7023
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7023
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7023
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7022
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7022
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7011
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7011
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7006
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7006

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