1-L-O-methyl-2-acetyl-3-p-cis-coumaryl-myo-inositol - Compound Card

1-L-O-methyl-2-acetyl-3-p-cis-coumaryl-myo-inositol

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1-L-O-methyl-2-acetyl-3-p-cis-coumaryl-myo-inositol

Structure
Zoomed Structure
  • Family: Plantae - Sapindaceae
  • Kingdom: Plantae
  • Class: Myo-Inositol Derivative
Canonical Smiles CO[C@H]1[C@@H](OC(=O)C)C(OC(=O)/C=C\c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C18H22O9/c1-9(19)26-18-16(25-2)14(23)13(22)15(24)17(18)27-12(21)8-5-10-3-6-11(20)7-4-10/h3-8,13-18,20,22-24H,1-2H3/b8-5-/t13-,14-,15+,16+,17?,18+/m0/s1
InChIKey AJZKDFNTXHJZSL-PYPDDJCDSA-N
Formula C18H22O9
HBA 9
HBD 4
MW 382.37
Rotatable Bonds 5
TPSA 142.75
LogP -0.64
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 382.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dodonaea viscosa Sapindaceae Plantae 151065

Showing of synonyms

  • Mostafa AE, El-Hela AA, et al. (2014). New secondary metabolites from Dodonaea viscosa. Phytochemistry Letters,2014,8,10-15. [View]
Pubchem: 163085615
Nmrshiftdb2: 70062569

No compound-protein relationship available.

Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 382.37 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 382.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 382.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.690
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.600
Plasma Protein Binding
50.71
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
9.650
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.420
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.950
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.260
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
-6.220
Rat (Acute)
2.290
Rat (Chronic Oral)
3.510
Fathead Minnow
4.080
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
428.280
Hydration Free Energy
-12.790
Log(D) at pH=7.4
0.510
Log(P)
0.51
Log S
-2.24
Log(Vapor Pressure)
-9.64
Melting Point
158.43
pKa Acid
6.73
pKa Basic
1.8
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 0.9275
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9275
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8948
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8948
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8630
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8630
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8550
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8550
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8547
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8547
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8533
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8533
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8418
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8418
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8364
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8364
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8363
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8363
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8314
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8314
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8258
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8258
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8223
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8223
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8209
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8209
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8152
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8152
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7847
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7847
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7833
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7833
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7810
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7810
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7799
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7799
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7721
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7721
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7707
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7707
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7689
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7689
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7638
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7638
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7609
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7609
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7552
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7552
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7448
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7448
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7436
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7436
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7331
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7331
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7319
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7319
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7299
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7299
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7285
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7285
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7264
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7264
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7237
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7237
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7211
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7211
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7209
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7209
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7186
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7186
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7159
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7159
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7126
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7126
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7088
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7088
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7074
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7049
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7049
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7045
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7045
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7039
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7039
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7038
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7038
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7029
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7029
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7022
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7022
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7012
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7012
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7004
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7004

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