Excelside B - Compound Card

Excelside B

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Excelside B

Structure
Zoomed Structure
  • Family: Plantae - Oleaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Secoiridoid Glucoside
Canonical Smiles C/C=C\1/C(OC=C([C@H]1CC(=O)OCCc1ccc(cc1)O)C(=O)OC)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C31H42O17/c1-3-16-17(10-21(34)43-9-8-14-4-6-15(33)7-5-14)18(28(41)42-2)12-44-29(16)48-31-27(40)25(38)23(36)20(47-31)13-45-30-26(39)24(37)22(35)19(11-32)46-30/h3-7,12,17,19-20,22-27,29-33,35-40H,8-11,13H2,1-2H3/b16-3+/t17-,19+,20+,22+,23+,24-,25-,26+,27+,29?,30+,31-/m0/s1
InChIKey FVQYDVAAZIXQID-AZCYGJOYSA-N
Formula C31H42O17
HBA 17
HBD 8
MW 686.66
Rotatable Bonds 12
TPSA 260.59
LogP -2.52
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 686.24
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Fraxinus excelsior Oleaceae Plantae 38873
2 Fraxinus excelsior Oleaceae Plantae 38873
3 Fraxinus angustifolia Oleaceae Plantae 166594

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]
  • García-Villalba R, Tomás-Barberán FA, et al. (2015). Targeted and untargeted metabolomics to explore the bioavailability of the secoiridoids from a seed/fruit extract (Fraxinus angustifolia Vahl) in human healthy volunteers: a preliminary study. Molecules,2015,20(12),22202-22219. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CCOC(=O)CC(C2=C)C=COC2OC(O3)CCCC3COC4CCCCO4

Level: 3

Mol. Weight: 686.66 g/mol

Structure

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

Level: 2

Mol. Weight: 686.66 g/mol

Structure

SMILES: C1C=COC(C1=C)OC(O2)CCCC2COC3CCCCO3

Level: 2

Mol. Weight: 686.66 g/mol

Structure

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

Level: 1

Mol. Weight: 686.66 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 686.66 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 686.66 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 686.66 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 686.66 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 686.66 g/mol

Adipocyte differentiation-inhibitory
Antidiabetic
Antiobesity property

Absorption

Caco-2 (logPapp)
-6.5
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
76.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
57.5
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
5.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.78
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.76
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
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-139867.58
Rat (Acute)
2.68
Rat (Chronic Oral)
4.63
Fathead Minnow
191.38
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
9754.24
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.24
Log(P)
-1.11
Log S
-2.43
Log(Vapor Pressure)
-327.12
Melting Point
167.96
pKa Acid
2.78
pKa Basic
2.66
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 0.8927
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8927
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8896
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8896
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8555
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8555
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8496
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8496
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8478
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8478
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
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7956
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7956
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7876
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7876
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7837
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7837
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7836
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7836
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7739
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7739
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7738
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7738
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7695
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7695
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7531
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7531
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7510
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7510
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7485
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7485
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7399
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7399
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7381
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7381
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 0.7331
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7331
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7315
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7315
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7297
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7297
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7286
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7286
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7278
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7278
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7277
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7277
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
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7261
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7261
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7251
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7251
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7250
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7250
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 3 0.7237
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 3 0.7237
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7230
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7230
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7214
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7214
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7194
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7194
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7193
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7193
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7191
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7191
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7181
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7181
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7172
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7172
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7158
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7158
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7157
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7157
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 0.7144
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7144
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7142
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7142
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7122
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7122
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7122
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7122
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7115
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7115
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7113
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7113
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7101
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7101
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7098
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7098
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7089
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7089
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7085
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7085
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7083
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7083
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7071
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7071
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7070
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7070
Malate dehydrogenase P10584 MDH_THETH Thermus thermophilus 3 0.7059
Malate dehydrogenase P10584 MDH_THETH Thermus thermophilus 3 0.7059
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7047
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7047
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7045
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7045
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7042
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7042
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7040
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7039
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7039
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7039
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7039
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7035
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7035
Genome polyprotein A9LIE0 A9LIE0_9FLAV dengue virus type 3 3 0.7032
Genome polyprotein A9LIE0 A9LIE0_9FLAV dengue virus type 3 3 0.7032
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7030
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7030
Genome polyprotein Q6YMS4 POLG_DEN3S Dengue virus type 3 3 0.7029
Genome polyprotein Q6YMS4 POLG_DEN3S Dengue virus type 3 3 0.7029
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7022
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7022
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 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7006
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7006
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7001
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7001

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