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Prunasin
- Family: Plantae - Myrtaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cyanogenic Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@H](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+/m0/s1 |
| InChIKey | ZKSZEJFBGODIJW-GMDXDWKASA-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 | Centaurea nicaeensis | Asteraceae | Plantae | 41503 |
| 2 | Syzygium samarangense | Myrtaceae | Plantae | 260143 |
Showing of synonyms
Prunasin
(R)-Prunasin
99-18-3
(2R)-Prunasin
(R)-(beta-D-Glucopyranosyloxy)phenylacetonitrile
D-Mandelonitrile-beta-D-glucoside
UNII-14W4BPM5FB
EINECS 202-738-0
14W4BPM5FB
(-)-Prunasin
BRN 0091509
CHEBI:17396
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
(-)-(2R)-Prunasin
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-, (R)-
DTXSID001018995
5-17-07-00405 (Beilstein Handbook Reference)
MANDELONITRILE GLUCOSIDE D-FORM
MANDELONITRILE GLUCOSIDE D-FORM [MI]
(2R)-(beta-D-glucosyloxy)(phenyl)acetonitrile
(2R)-2-phenyl-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile
Prunasine
Benzeneacetonitrile, .alpha.-(.beta.-D-glucopyranosyloxy)-, (R)-
BENZENEACETONITRILE, .ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-, (.ALPHA.R)-
Prunasin, (R)-isomer
CHEBI:25150
D-Mandelonitrile-.beta.-D-glucoside
(2R)-2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)acetonitrile
(2R)-2-phenyl-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyacetonitrile
Glucopyranoside, D-mandelonitrile, .beta.-D-
Mandelonitrile, .beta.-D-glucopyranoside, D-
PRUNASIN [INCI]
Acetonitrile, (.beta.-D-glucopyranosyloxy)phenyl-, D-
Mandelonitrile-beta-glucoside
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-(9CI)
(R)-Mandelonitrile b-D-glucoside
DTXCID201476997
(R)-Mandelonitrile I2-D-glucoside
(R)-Mandelonitrile b-D-glucopyranoside
(R)-Mandelonitrile I2-D-glucopyranoside
Glucopyranoside, D-mandelonitrile, beta-D-
Mandelonitrile, beta-D-glucopyranoside, D-
(R)-(b-D-Glucopyranosyloxy)phenylacetonitrile
(R)-a-(b-D-Glucopyranosyloxy)benzene-acetonitrile
Acetonitrile, (beta-D-glucopyranosyloxy)phenyl-, D-
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-, (R)-(9CI)
BENZENEACETONITRILE, ALPHA-(BETA-D-GLUCOPYRANOSYLOXY)-, (ALPHAR)-
(beta-d-glucopyranosyloxy)(phenyl)acetonitrile
138-53-4
Alpha-(beta-d-glucopyranosyloxy)benzeneacetonitrile
Benzeneacetonitrile, .alpha.-(.beta.-d-glucopyranosyloxy)-
Benzeneacetonitrile, alpha-(beta-d-glucopyranosyloxy)-
D,l-mandelonitrile-beta-d-glucoside
Mandelonitrile .beta.-d-glucopyranoside
Mandelonitrile beta-d-glucopyranoside
Mandelonitrile beta-d-glucoside
Zkszejfbgodijw-qehjdlsmsa-n
D-Prunasin
(R)-alpha-(beta-D-Glucopyranosyloxy)benzene-acetonitrile
(R)-mandelonitrile beta-D-glucoside
(R)-mandelonitrile beta-D-glucopyranoside
(R)-2-Phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile
(2R)-(beta-D-glucopyranosyloxy)(phenyl)acetonitrile
R-Prunasin
SCHEMBL377612
CHEMBL1778417
GLXC-19023
HY-N1548
MSK158598
AKOS032948360
FP27250
AS-75874
DA-66974
1ST158598
CS-0017097
NS00079018
C00844
F82086
(a-R)-a-(b-D-Glucopyranosyloxy)benzeneacetonitrile
Q7253027
- Hammoud L, Seghiri R, et al. (2012). A new flavonoid and other constituents from Centaurea nicaeensis All. var. walliana M.. Natural Product Research,2012,26(3),203-208. [View] [PubMed]
- Samy M.N, Sugimoto S, et al. (2014). Taxiphyllin 6-O-Gallate, Actinidioionoside 6-O-Gallate and Myricetrin 2-O-Sulfate from the Leaves of Syzygium samarangense and Their Biological Activities. Chemical & pharmaceutical bulletin,2014, 62(10), 1013-8. [View] [PubMed]
Pubchem:
119033
Cas:
99-18-3
Gnps:
CCMSLIB00005716579
Zinc:
ZINC000004095477
Chebi:
17396
Nmrshiftdb2:
60026778
Metabolights:
MTBLC17396
Chembl:
CHEMBL1778417
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)
- -5.19
- 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
- -1.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.560
- Plasma Protein Binding
- 63.82
- 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
- 5.310
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.720
- 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
- 4.140
- 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
- -4.030
- Rat (Acute)
- 2.640
- Rat (Chronic Oral)
- 3.080
- Fathead Minnow
- 3.860
- 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
- 387.820
- Hydration Free Energy
- -15.820
- Log(D) at pH=7.4
- -0.310
- Log(P)
- -0.66
- Log S
- -1.62
- Log(Vapor Pressure)
- -10.52
- Melting Point
- 149.63
- pKa Acid
- 5.44
- 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 |