Fraxicarboside B - Compound Card

Fraxicarboside B

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Fraxicarboside B

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)O)O
InChI InChI=1S/C34H38O17/c1-46-32(45)21-15-49-33(19(8-10-35)20(21)14-28(41)47-11-9-18-3-6-23(37)25(39)13-18)51-34-31(44)30(43)29(42)26(50-34)16-48-27(40)7-4-17-2-5-22(36)24(38)12-17/h2-8,12-13,15,20,26,29-31,33-39,42-44H,9-11,14,16H2,1H3/b7-4+,19-8+/t20-,26+,29+,30-,31+,33-,34-/m0/s1
InChIKey VXKXMAPMMYGLJE-VPMGPIIOSA-N
Formula C34H38O17
HBA 17
HBD 8
MW 718.66
Rotatable Bonds 13
TPSA 268.43
LogP 0.01
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 51
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 718.21
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: 718.66 g/mol

Structure

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

Level: 2

Mol. Weight: 718.66 g/mol

Structure

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

Level: 2

Mol. Weight: 718.66 g/mol

Structure

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

Level: 1

Mol. Weight: 718.66 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 718.66 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 718.66 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 718.66 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 718.66 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 718.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-3.22
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
297.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
57.71
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.75
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-4.45
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.87
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.19
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
-542196.22
Rat (Acute)
2.35
Rat (Chronic Oral)
4.93
Fathead Minnow
698.57
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
53313.81
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.18
Log(P)
0.81
Log S
-4.16
Log(Vapor Pressure)
-1800.36
Melting Point
198.62
pKa Acid
3.34
pKa Basic
2.46
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 0.9336
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9336
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 0.9145
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9145
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9002
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9002
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8805
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8805
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8734
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8734
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8703
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8703
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8694
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8694
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8647
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8647
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8527
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8527
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8481
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8481
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8382
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8382
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8352
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8352
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8340
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8340
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8271
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8271
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8233
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8233
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.8223
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.8223
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8218
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8218
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8209
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8209
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8138
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8138
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8032
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8032
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7951
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7951
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7943
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7943
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7908
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7908
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7889
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7889
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7829
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7829
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7816
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7816
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7812
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7812
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7805
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7805
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7791
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7791
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7752
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7752
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7733
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7733
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7723
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7723
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7709
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7709
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7681
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7681
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7656
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7656
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7584
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7584
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7561
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7561
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7522
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7522
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7510
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7510
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7497
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7497
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7491
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7491
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7453
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7453
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7422
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7422
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7384
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7384
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7374
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7374
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7333
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7333
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7331
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7331
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7314
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7314
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7255
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7255
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7251
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7251
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7244
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7244
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7236
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7236
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 4 0.7227
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 4 0.7227
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7197
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7197
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7191
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7191
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7186
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7186
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7174
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7174
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7168
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7168
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7161
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7161
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7160
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7160
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7153
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7153
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7149
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7149
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7119
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7119
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7118
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7118
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7118
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7118
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7112
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7112
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7093
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7093
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7080
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7080
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7069
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7069
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7055
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7055
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7050
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7050
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7035
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7035
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7007
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7007
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7005
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7005
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7002
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7002

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