10-hydroxyoleuropein - Compound Card

10-hydroxyoleuropein

Select a section from the left sidebar

10-hydroxyoleuropein

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](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C25H32O14/c1-35-23(34)15-11-37-24(39-25-22(33)21(32)20(31)18(10-27)38-25)13(4-6-26)14(15)9-19(30)36-7-5-12-2-3-16(28)17(29)8-12/h2-4,8,11,14,18,20-22,24-29,31-33H,5-7,9-10H2,1H3/b13-4+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
InChIKey JCWFMPVGIIRRRG-AXPMACIOSA-N
Formula C25H32O14
HBA 14
HBD 7
MW 556.52
Rotatable Bonds 10
TPSA 221.9
LogP -1.66
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 556.18
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]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 556.52 g/mol

Structure

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

Level: 1

Mol. Weight: 556.52 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 556.52 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 556.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 556.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 556.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.13
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
58.81
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
9.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.78
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.85
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
-1620.41
Rat (Acute)
2.46
Rat (Chronic Oral)
4.41
Fathead Minnow
4.73
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
556.23
Hydration Free Energy
-2.93
Log(D) at pH=7.4
-0.02
Log(P)
-1.06
Log S
-2.53
Log(Vapor Pressure)
-11.58
Melting Point
162.39
pKa Acid
4.5
pKa Basic
3.36
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 0.9123
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9123
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9052
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9052
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8866
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8866
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8826
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8826
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8605
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8605
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8585
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8585
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8492
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8492
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8426
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8426
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8378
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8378
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8360
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8360
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8350
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8350
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8278
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8278
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8222
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8222
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8208
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8208
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8112
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8112
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8112
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8112
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8084
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8084
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7938
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7938
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7920
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7920
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7909
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7909
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7908
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7908
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7878
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7878
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7874
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7874
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7808
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7808
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7779
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7779
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7764
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7764
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7760
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7760
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7760
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7760
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7735
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7735
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7692
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7692
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7687
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7687
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7671
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7671
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7655
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7655
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7602
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7602
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7519
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7519
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7489
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7489
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7447
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7447
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7425
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7425
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7400
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7400
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7390
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7390
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7369
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7369
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7356
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7356
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7284
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7284
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7261
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7261
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7257
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7257
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7257
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7257
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7240
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7240
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7232
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7232
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7223
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7223
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7223
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7223
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7172
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7172
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7167
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7167
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7154
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7154
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7154
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7154
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7145
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7145
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7101
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7101
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7088
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7088
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7083
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7083
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7068
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7068
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7061
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7061
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7058
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7058
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7056
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7056
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7047
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7047
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7047
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7047
Malate dehydrogenase P10584 MDH_THETH Thermus thermophilus 3 0.7046
Malate dehydrogenase P10584 MDH_THETH Thermus thermophilus 3 0.7046
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7044
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7044
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7032
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7032
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7030
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7030
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7030
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7030
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7022
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7022
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7014
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7014
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7007
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7007
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7001
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7001

Download SDF