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Prulaurasin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Nitrile
- Subclass: Cyanohydrin Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](OC(c2ccccc2)C#N)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9?,10-,11-,12+,13-,14-/m1/s1 |
| InChIKey | ZKSZEJFBGODIJW-MXNNCRBYSA-N |
| Formula | C14H17NO6 |
| HBA | 7 |
| HBD | 4 |
| MW | 295.29 |
| Rotatable Bonds | 4 |
| TPSA | 123.17 |
| LogP | -0.93 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 295.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Gerbera jamesonii | Asteraceae | Plantae | 13547 |
Showing of synonyms
Prulaurasin
Mandelonitrile glucoside
138-53-4
D,L-Mandelonitrile-beta-D-glucoside
Mandelonitrile beta-D-glucopyranoside
Alpha-(beta-D-Glucopyranosyloxy)benzeneacetonitrile
(DL)-Prunasin
UNII-4J1L0618WK
4J1L0618WK
2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
Mandelonitrile beta-D-glucoside
(beta-D-glucopyranosyloxy)(phenyl)acetonitrile
MANDELONITRILE GLUCOSIDE [MI]
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-
MANDELONITRILE GLUCOSIDE DL-FORM
MANDELONITRILE GLUCOSIDE [WHO-DD]
MANDELONITRILE GLUCOSIDE DL-FORM [MI]
MANDELONITRILE .BETA.-D-GLUCOPYRANOSIDE
Alpha-(beta-D-Glucopyranosyloxy)-Benzeneacetonitrile
BENZENEACETONITRILE, .ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-
Prunasin, (R)-isomer
2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
2-phenyl-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyacetonitrile
2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)acetonitrile
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-(9CI)
Mandelonitrile b-D-glucoside
Mandelonitrile I2-D-glucoside
D,L-Mandelonitrile-b-D-glucoside
Mandelonitrile b-D-glucopyranoside
D,L-Mandelonitrile-I2-D-glucoside
Mandelonitrile I2-D-glucopyranoside
A-(b-D-Glucopyranosyloxy)benzeneacetonitrile
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)- (9CI)
Alpha-Cyanobenzyl beta-D-glucopyranoside
SCHEMBL440675
MEGxp0_000351
ACon1_000529
DTXSID801020158
AKOS040752923
NCGC00168992-01
NCGC00168992-02
.ALPHA.-CYANOBENZYL .BETA.-D-GLUCOPYRANOSIDE
BRD-A06421966-001-01-9
Q27893921
- Halim AF, Marwan ESM, et al. (1980). 6-hydroxy-4-methoxy-5-methylcoumarin from Gerbera jamesonii. Phytochemistry,1980,19,2496-2496. [View]
Pubchem:
120639
Cas:
138-53-4
Gnps:
CCMSLIB00004698597
Chebi:
25150
Nmrshiftdb2:
75353
Metabolights:
MTBLC25150
CPRiL:
122535
SMILES: c1ccccc1COC2CCCCO2
Level: 1
Mol. Weight: 295.29 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 295.29 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 295.29 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.18
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.470
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.560
- Plasma Protein Binding
- 60.89
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 5.340
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.730
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.800
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.150
- 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
- -2.230
- Rat (Acute)
- 2.640
- Rat (Chronic Oral)
- 3.070
- Fathead Minnow
- 3.870
- 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
- 386.370
- Hydration Free Energy
- -15.800
- Log(D) at pH=7.4
- -0.280
- Log(P)
- -0.62
- Log S
- -1.6
- Log(Vapor Pressure)
- -10.46
- Melting Point
- 147.46
- pKa Acid
- 5.42
- pKa Basic
- 3.32
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.8698 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.8698 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8483 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8483 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8465 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.8465 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8288 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8288 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7978 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7978 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7878 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7878 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7765 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7765 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7734 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7734 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7620 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7620 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7477 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7477 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7477 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7477 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7440 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7440 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7429 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7429 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7416 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7416 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7351 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7351 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7347 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7347 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7298 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7298 |
| Methionine--tRNA ligase | P00959 | SYM_ECOLI | Escherichia coli | 3 | 0.7282 |
| Methionine--tRNA ligase | P00959 | SYM_ECOLI | Escherichia coli | 3 | 0.7282 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7277 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7277 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7245 |
| 1-deoxy-D-xylulose 5-phosphate reductoisomerase | P45568 | DXR_ECOLI | Escherichia coli | 2 | 0.7245 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7216 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7216 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7174 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7174 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7154 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7154 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7152 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7152 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7148 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7148 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7138 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7138 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7113 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7113 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7104 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7104 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7084 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7084 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7040 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7040 |