1-O-acetyl prinsepiol - Compound Card

1-O-acetyl prinsepiol

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1-O-acetyl prinsepiol

Structure
Zoomed Structure
  • Family: Cistaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles COc1cc(ccc1O)[C@H]1OC[C@]2([C@@]1(CO[C@@H]2c1ccc(c(c1)OC)O)OC(=O)C)O
InChI InChI=1S/C22H24O9/c1-12(23)31-22-11-30-19(13-4-6-15(24)17(8-13)27-2)21(22,26)10-29-20(22)14-5-7-16(25)18(9-14)28-3/h4-9,19-20,24-26H,10-11H2,1-3H3/t19-,20-,21+,22+/m1/s1
InChIKey YFFCEARGDVTSAJ-CZYKHXBRSA-N
Formula C22H24O9
HBA 9
HBD 3
MW 432.43
Rotatable Bonds 5
TPSA 123.91
LogP 1.99
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 432.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Helianthemum sessiliflorum Cistaceae Plantae 2650562

Showing of synonyms

  • Benabdelaziz I, Haba H, et al. (2015). Lignans and other constituents from Helianthemum sessiliflorum Pers.. Records of Natural Products,2015,9(3),342-348. [View]
Pubchem: 162817380

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 266.34 g/mol

Structure

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 190.24 g/mol

Structure

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 114.14 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.61
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.760
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.880
Plasma Protein Binding
72.39
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
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
13.080
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.420
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.770
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.920
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
-52.930
Rat (Acute)
2.220
Rat (Chronic Oral)
2.750
Fathead Minnow
4.100
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
437.400
Hydration Free Energy
-3.480
Log(D) at pH=7.4
2.200
Log(P)
0.88
Log S
-3.82
Log(Vapor Pressure)
-9.1
Melting Point
189.24
pKa Acid
7.25
pKa Basic
1.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9307
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9307
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9289
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9289
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9016
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9016
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8908
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8908
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8799
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8799
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8753
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8753
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8731
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8731
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8660
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8660
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8599
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8599
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8548
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8548
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8436
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8436
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8401
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.8401
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.8305
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.8305
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8278
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8278
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8232
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8232
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8157
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8157
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8074
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8074
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8047
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8047
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8034
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8034
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8030
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8030
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8011
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8011
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7995
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7995
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7971
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7971
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7890
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7890
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7886
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7886
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7878
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7878
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7819
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7819
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7803
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7803
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7761
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7761
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7761
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7761
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7595
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7595
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7592
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7592
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7524
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7524
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7514
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7514
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 4 0.7510
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 4 0.7510
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7506
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7506
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7496
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7496
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7464
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7464
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7432
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7432
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7396
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7396
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7365
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7365
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7345
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7345
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7315
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7315
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7290
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7290
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7259
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7259
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7244
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7244
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7206
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7206
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7199
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7199
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7199
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7199
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7177
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7177
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7169
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7169
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7168
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7168
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7162
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7162
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7150
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7150
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7147
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7147
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7128
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7128
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7116
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7116
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7111
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7111
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7108
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7108
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7103
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7103
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7103
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7103
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7083
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7083
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7059
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7059
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 4 0.7057
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7057
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7057
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 4 0.7057
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7057
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7057
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7056
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7056
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7052
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7052
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7049
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7049
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7046
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7046
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7025
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7025
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7020
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7020
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7019
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7019
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7018
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7018
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7017
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7017
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7016
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7016
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7012
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7012
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7003
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7003

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