Fraxicarboside C - Compound Card

Fraxicarboside C

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Fraxicarboside C

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(c(c2)O)O)[C@H]([C@@H]([C@H]1O)OC(=O)C)O
InChI InChI=1S/C36H40O18/c1-18(38)52-33-31(45)28(17-50-29(43)8-5-19-3-6-24(39)26(41)13-19)53-36(32(33)46)54-35-21(9-11-37)22(23(16-51-35)34(47)48-2)15-30(44)49-12-10-20-4-7-25(40)27(42)14-20/h3-9,13-14,16,22,28,31-33,35-37,39-42,45-46H,10-12,15,17H2,1-2H3/b8-5+,21-9+/t22-,28+,31+,32+,33-,35-,36-/m0/s1
InChIKey MPAWGZHLBSDDEL-YMIZOKTQSA-N
Formula C36H40O18
HBA 18
HBD 7
MW 760.7
Rotatable Bonds 14
TPSA 274.5
LogP 0.58
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 54
Formal Charge 0
Fraction CSP3 0.39
Exact Mass 760.22
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]
Pubchem: 102316373

No compound-protein relationship available.

Structure

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

Level: 3

Mol. Weight: 760.7 g/mol

Structure

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

Level: 2

Mol. Weight: 760.7 g/mol

Structure

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

Level: 2

Mol. Weight: 760.7 g/mol

Structure

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

Level: 1

Mol. Weight: 760.7 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 760.7 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 760.7 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 760.7 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 760.7 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 760.7 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.33
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
2.87
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1097.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
58.79
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
12.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-25.93
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.0
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.79
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
-1996902.98
Rat (Acute)
2.43
Rat (Chronic Oral)
4.69
Fathead Minnow
2528.49
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
217979.96
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.66
Log(P)
1.42
Log S
-4.19
Log(Vapor Pressure)
-7171.65
Melting Point
197.35
pKa Acid
-20.13
pKa Basic
0.42
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 0.9361
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9361
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9308
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9308
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9175
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9175
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9087
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9087
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8829
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8829
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8723
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8723
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8667
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8667
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8633
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8633
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8435
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8435
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8380
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8380
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 0.8278
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8278
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8264
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8264
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8243
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8243
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8148
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8148
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8048
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8048
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8031
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8031
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7842
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7842
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7833
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7833
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7747
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7747
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7732
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7732
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7721
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7721
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7627
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7627
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7547
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7547
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7545
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7545
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7542
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7542
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7518
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7518
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7506
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7506
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7502
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7502
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7498
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7498
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7495
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7495
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7467
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7467
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7450
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7450
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7421
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7421
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7350
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7350
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7324
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7324
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7291
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7291
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7283
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7283
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7279
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7279
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7269
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7269
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7255
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7255
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7239
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7239
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7186
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7186
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7185
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7185
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7178
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7178
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7176
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7176
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7171
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7171
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7164
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7164
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7138
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7138
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7136
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7136
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7135
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7135
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7131
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7131
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7120
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7120
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7100
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7100
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7070
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7070
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7057
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7057
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7047
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7047
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7036
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7036
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7034
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7034
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7033
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7033
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7028
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7028
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7027
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7027
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7018
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7018
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7016
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7016
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7006
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7006

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