Angustifolioside C - Compound Card

Angustifolioside C

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Angustifolioside C

Structure
Zoomed Structure
  • Family: Plantae - Oleaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Secoiridoid Glucoside
Canonical Smiles C/C=C/1\[C@@H](OC=C(C1CC(=O)OCCc1ccc(c(c1)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C(=O)OCCc1ccc(c(c1)O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C38H48O20/c1-2-19-20(13-28(44)52-9-7-18-4-6-25(24(43)12-18)55-37-33(49)31(47)29(45)26(14-39)56-37)21(35(51)53-10-8-17-3-5-22(41)23(42)11-17)16-54-36(19)58-38-34(50)32(48)30(46)27(15-40)57-38/h2-6,11-12,16,20,26-27,29-34,36-43,45-50H,7-10,13-15H2,1H3/b19-2-/t20?,26-,27-,29-,30-,31+,32+,33-,34-,36+,37-,38+/m1/s1
InChIKey VXNIBTFXSAVWKH-KRHCFSBYSA-N
Formula C38H48O20
HBA 20
HBD 11
MW 824.78
Rotatable Bonds 15
TPSA 321.28
LogP -2.14
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 58
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 824.27
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Fraxinus angustifolia Oleaceae Plantae 166594

Showing of synonyms

  • Calis I, Hosny M, et al. (1996). A secoiridoid glucoside from Fraxinus angustifolia. Phytochemistry,1996,41(6),1557-1562. [View]
Pubchem: 101695757

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1Oc(cc2)ccc2CCOC(=O)CC3C(=C)C(OC4CCCCO4)OC=C3C(=O)OCCc5ccccc5

Level: 4

Mol. Weight: 824.78 g/mol

Structure

SMILES: c1ccccc1CCOC(=O)CC2C(=C)C(OC3CCCCO3)OC=C2C(=O)OCCc4ccccc4

Level: 3

Mol. Weight: 824.78 g/mol

Structure

SMILES: O1CCCCC1Oc(cc2)ccc2CCOC(=O)CC3C(=C)COC=C3C(=O)OCCc4ccccc4

Level: 3

Mol. Weight: 824.78 g/mol

Structure

SMILES: O1CCCCC1OC2OC=CC(C2=C)CC(=O)OCCc3ccc(cc3)OC4CCCCO4

Level: 3

Mol. Weight: 824.78 g/mol

Structure

SMILES: c1ccccc1CCOC(=O)CC2C(=C)COC=C2C(=O)OCCc3ccccc3

Level: 2

Mol. Weight: 824.78 g/mol

Structure

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

Level: 2

Mol. Weight: 824.78 g/mol

Structure

SMILES: C1OC=CC(C1=C)CC(=O)OCCc2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 824.78 g/mol

Structure

SMILES: c1ccccc1CCOC(=O)C2=COC(C(=C)C2)OC3CCCCO3

Level: 2

Mol. Weight: 824.78 g/mol

Structure

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

Level: 1

Mol. Weight: 824.78 g/mol

Structure

SMILES: C=C(C1)COC=C1C(=O)OCCc2ccccc2

Level: 1

Mol. Weight: 824.78 g/mol

Structure

SMILES: C1C=COC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 824.78 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 824.78 g/mol

Structure

SMILES: C=C1CC=COC1

Level: 0

Mol. Weight: 824.78 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 824.78 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 824.78 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
69.11
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
9829.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
58.54
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
6.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-228.39
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.88
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
-17840409.04
Rat (Acute)
2.4
Rat (Chronic Oral)
5.24
Fathead Minnow
22528.03
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
2000212.36
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.02
Log(P)
-0.91
Log S
-3.8
Log(Vapor Pressure)
-65786.24
Melting Point
212.9
pKa Acid
-422.66
pKa Basic
5.83
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 0.9371
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9371
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9280
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9280
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9215
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9215
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9117
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9117
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8876
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8876
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8521
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8521
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8459
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8459
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8366
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8366
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8351
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8351
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8298
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8298
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8276
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8276
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8179
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8179
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8165
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8165
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8081
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8081
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8014
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8014
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7986
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7986
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7986
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7986
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7964
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7964
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7915
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7915
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7879
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7879
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7821
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7821
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7798
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7798
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7780
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 4 0.7780
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7773
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7773
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7761
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7761
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7741
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7741
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7699
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7699
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7657
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7657
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7640
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7640
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7614
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7614
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7558
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7558
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7541
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7541
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7520
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7520
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7510
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7510
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7497
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7497
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7497
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7497
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7434
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7434
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7368
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7368
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7365
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7365
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7364
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7364
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7354
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7354
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7307
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7307
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7278
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7278
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7225
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7225
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7198
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7198
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7182
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7182
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7174
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7174
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7132
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7132
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7120
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7120
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7118
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7118
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7116
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7116
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7111
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7111
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7100
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7100
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7090
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7090
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7085
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7085
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7084
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7084
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7064
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7064
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7046
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7046
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7045
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7045
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7044
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 3 0.7044
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7043
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7043
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7039
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7039
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7031
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7031
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7026
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7026
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7011
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7011
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7008
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7008
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7008
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7008
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7007
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7007
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7006
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7006
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7006
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7006
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7000
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7000

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