Ligstroside - Compound Card

Ligstroside

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Ligstroside

Structure
Zoomed Structure
  • Family: Plantae - Oleaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Secoiridoid Glucoside
Canonical Smiles OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H](/C/2=C\C)CC(=O)OCCc2ccc(cc2)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3+/t16-,18+,20+,21-,22+,24-,25-/m0/s1
InChIKey GMQXOLRKJQWPNB-MVVLSVRYSA-N
Formula C25H32O12
HBA 12
HBD 5
MW 524.52
Rotatable Bonds 9
TPSA 181.44
LogP -0.34
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 524.19
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Fraxinus excelsior Oleaceae Plantae 38873
2 Fraxinus excelsior Oleaceae Plantae 38873
3 Fraxinus angustifolia Oleaceae Plantae 166594
4 Fraxinus angustifolia Oleaceae Plantae 166594
5 Fraxinus oxycarba Oleaceae Plantae 38871

Showing of synonyms

  • Ibarra A, Bai N, et al. (2011). Fraxinus excelsior seed extract FraxiPureTM limits weight gains and hyperglycemia in high-fat diet-induced obese mice. Phytomedicine,2011,18(6),479-485. [View]
  • Bai N, He K, et al. (2010). Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and PPARalpha activation activity. Journal of Natural Products,2010,73(1),2-6. [View] [PubMed]
  • Hosny M (1998). Secoiridoid glucosides from Fraxinus oxycarba. Phytochemistry,1998,47(8),1569-1576. [View]
  • Calis I, Hosny M, et al. (1993). Secoiridoids from Fraxinus angustifolia. Phytochemistry,1993,33(6),1453-1456. [View]
  • Hosny M, Ca̧liş I, et al. (1991). Secoiridoids from Fraxinus angustifolia. Planta Medica,1991,2-A81. [View]
CPRiL: 93868
Structure

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

Level: 2

Mol. Weight: 524.52 g/mol

Structure

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

Level: 1

Mol. Weight: 524.52 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 524.52 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 524.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 524.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 524.52 g/mol

Adipocyte differentiation-inhibitory
Antiobesity property

Absorption

Caco-2 (logPapp)
-6.06
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
70.29
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.530
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.300
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.730
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.800
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
-692.430
Rat (Acute)
2.480
Rat (Chronic Oral)
4.040
Fathead Minnow
4.560
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
503.050
Hydration Free Energy
-2.960
Log(D) at pH=7.4
1.250
Log(P)
0.09
Log S
-2.62
Log(Vapor Pressure)
-11.58
Melting Point
159.49
pKa Acid
5.44
pKa Basic
2.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8854
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8854
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8658
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8658
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8230
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8230
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8152
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8152
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8065
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8065
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7982
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7982
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7793
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7793
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7792
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7792
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7716
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7716
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7700
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7700
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7511
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7462
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7462
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 3 0.7434
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 3 0.7434
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7405
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7405
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7384
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7384
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7381
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7381
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7378
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7378
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7372
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7372
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
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7310
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7310
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7291
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7291
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7266
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7266
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7255
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7255
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7217
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7217
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7213
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7213
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7208
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7208
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7205
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7205
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7180
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7180
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7169
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7169
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7165
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7165
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7158
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7158
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7146
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7146
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7127
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7127
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7117
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7117
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7094
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7094
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7091
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7091
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7087
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7087
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7068
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7068
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7067
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7067
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7064
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7064
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7058
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7058
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7057
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7057
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7050
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7050
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7047
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7047
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7047
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7047
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7043
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7043
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7037
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7037
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7032
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7032
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7027
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7027
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7025
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7025
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7017
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7017
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
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7002
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7002
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7002
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7002

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