Fraxicarboside A - Compound Card

Fraxicarboside A

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Fraxicarboside A

Structure
Zoomed Structure
  • Family: Plantae - Oleaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Secoiridoid Glucoside
Canonical Smiles OC/C=C\1/[C@@H](OC=C([C@H]1CC(=O)OCCc1ccc(c(c1)O)O)C(=O)OC)O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C34H38O16/c1-45-32(44)23-16-48-33(21(10-12-35)22(23)15-28(40)46-13-11-19-4-8-24(37)25(38)14-19)50-34-31(43)30(42)29(41)26(49-34)17-47-27(39)9-5-18-2-6-20(36)7-3-18/h2-10,14,16,22,26,29-31,33-38,41-43H,11-13,15,17H2,1H3/b9-5+,21-10+/t22-,26+,29+,30-,31+,33-,34-/m0/s1
InChIKey NRLPHLGFOVIHKP-PELURSKQSA-N
Formula C34H38O16
HBA 16
HBD 7
MW 702.66
Rotatable Bonds 13
TPSA 248.2
LogP 0.31
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 50
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 702.22
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Fraxinus oxycarba Oleaceae Plantae 38871

Showing of synonyms

  • Hosny M (1998). Secoiridoid glucosides from Fraxinus oxycarba. Phytochemistry,1998,47(8),1569-1576. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3OC=CC(C3=C)CC(=O)OCCc4ccccc4

Level: 3

Mol. Weight: 702.66 g/mol

Structure

SMILES: c1ccccc1CCOC(=O)CC(C2=C)C=COC2OC3CCCCO3

Level: 2

Mol. Weight: 702.66 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(C3=C)OC=CC3

Level: 2

Mol. Weight: 702.66 g/mol

Structure

SMILES: C1OC=CC(C1=C)CC(=O)OCCc2ccccc2

Level: 1

Mol. Weight: 702.66 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 702.66 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 702.66 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 702.66 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 702.66 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 702.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.52
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-3.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
202.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.68
Plasma Protein Binding
60.74
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
10.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.97
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.88
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.46
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
-371844.87
Rat (Acute)
2.42
Rat (Chronic Oral)
4.84
Fathead Minnow
484.07
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
34543.68
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.56
Log(P)
1.22
Log S
-3.98
Log(Vapor Pressure)
-1177.38
Melting Point
187.3
pKa Acid
4.01
pKa Basic
1.78
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 0.9340
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9340
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9291
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9291
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9138
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9138
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8875
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8875
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8777
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8777
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8768
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8768
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8660
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8660
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8603
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8603
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8578
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8578
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8499
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8499
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8478
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8478
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8358
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8358
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8344
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8344
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8333
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8333
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8332
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8332
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8300
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8300
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8237
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8237
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8235
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8235
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.8184
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.8184
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8075
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8075
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8074
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7938
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7938
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7916
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7916
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7798
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7798
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7776
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7776
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7719
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7719
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7681
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7681
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7637
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7637
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7605
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7605
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7586
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7586
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7566
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7566
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7547
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7547
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7527
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7527
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7524
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7524
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
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7481
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7481
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7476
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7476
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7461
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7461
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7429
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7429
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7420
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7420
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7415
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7415
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7375
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7375
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7373
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7373
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7288
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7288
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7272
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7272
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7272
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7272
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7258
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7258
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7255
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7255
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7252
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7252
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7223
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7223
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7211
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7211
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7190
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7190
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7186
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7186
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7183
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7183
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7180
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7180
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7151
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7151
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7135
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7135
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7134
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7134
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7119
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7119
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7111
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7111
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7103
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7103
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7098
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7098
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7097
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7097
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7094
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7094
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7063
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7063
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7057
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7057
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7055
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7055
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7054
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7054
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7045
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7045
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7040
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7039
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7039
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7032
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7032
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7027
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7027
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7025
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7025
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7023
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7023
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7017
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7017
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7012
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7012
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7012
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7012

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