10-hydroxyligstroside - Compound Card

10-hydroxyligstroside

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10-hydroxyligstroside

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(cc1)O)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C25H32O13/c1-34-23(33)17-12-36-24(38-25-22(32)21(31)20(30)18(11-27)37-25)15(6-8-26)16(17)10-19(29)35-9-7-13-2-4-14(28)5-3-13/h2-6,12,16,18,20-22,24-28,30-32H,7-11H2,1H3/b15-6+/t16-,18+,20+,21-,22+,24-,25-/m0/s1
InChIKey AHTRGGWSBFOEEG-HFLHEASMSA-N
Formula C25H32O13
HBA 13
HBD 6
MW 540.52
Rotatable Bonds 10
TPSA 201.67
LogP -1.37
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 540.18
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: 14756316
Nmrshiftdb2: 60025668

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 540.52 g/mol

Structure

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

Level: 1

Mol. Weight: 540.52 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 540.52 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 540.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 540.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 540.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
61.01
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
8.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.15
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.63
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.08
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
-1112.57
Rat (Acute)
2.67
Rat (Chronic Oral)
4.37
Fathead Minnow
3.93
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
532.82
Hydration Free Energy
-2.94
Log(D) at pH=7.4
0.51
Log(P)
-0.67
Log S
-2.29
Log(Vapor Pressure)
-11.48
Melting Point
149.41
pKa Acid
4.53
pKa Basic
2.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9470
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9470
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9100
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9100
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8559
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8559
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8540
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8540
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8156
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8156
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8121
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8121
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.8081
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.8081
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8035
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8035
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7818
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7818
1,4-alpha-glucan branching enzyme GlgB A7ZSW5 GLGB_ECO24 Escherichia coli O139:H28 3 0.7707
1,4-alpha-glucan branching enzyme GlgB A7ZSW5 GLGB_ECO24 Escherichia coli O139:H28 3 0.7707
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7691
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7691
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7652
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7652
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7574
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7574
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7509
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7509
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7492
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7492
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7431
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7431
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7424
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7424
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7411
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7411
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7401
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7401
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7368
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7368
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7368
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7368
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7364
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7364
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7328
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7328
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7299
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7299
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7292
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7292
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7291
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7291
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7284
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7284
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7274
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7274
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7260
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7260
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7257
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7257
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7231
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7231
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7220
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7220
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7218
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7218
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7215
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7215
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7214
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7214
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7206
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7206
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7196
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7196
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7195
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7195
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7168
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7168
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7166
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7166
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7157
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7157
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7157
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7157
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7154
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7154
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7153
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7153
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7144
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7144
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7142
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7142
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7118
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7118
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7113
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7113
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7111
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7111
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7106
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7106
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7106
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7106
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7103
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7103
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7095
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7095
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7090
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7090
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7076
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7076
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7070
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7070
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7066
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7066
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7064
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7064
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7064
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7064
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7059
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7059
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7055
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7055
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7054
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7048
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7048
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7046
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7046
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7037
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7037
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7035
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7035
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7034
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7034
adenine phosphoribosyltransferase Q967M2 Q967M2_GIAIN Giardia intestinalis 2 0.7011
adenine phosphoribosyltransferase Q967M2 Q967M2_GIAIN Giardia intestinalis 2 0.7011
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7009
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7009
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7008
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7008
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7006
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7006
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7004
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7004
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 2 0.7003
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 2 0.7003

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