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Dhurrin
- Family: Plantae - Proteaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenol Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H](c2ccc(cc2)O)C#N)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10-,11-,12+,13-,14-/m1/s1 |
| InChIKey | NVLTYOJHPBMILU-YOVYLDAJSA-N |
| Formula | C14H17NO7 |
| HBA | 8 |
| HBD | 5 |
| MW | 311.29 |
| Rotatable Bonds | 4 |
| TPSA | 143.4 |
| LogP | -1.23 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 311.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Campylospermum sulcatum | Ochnaceae | Plantae | 1321793 |
| 2 | Macadamia integrifolia | Proteaceae | Plantae | 60698 |
Showing of synonyms
Dhurrin
UNII-P5999IY65C
P5999IY65C
(S)-4-Hydroxymandelonitrile beta-D-glucoside
DHURRIN [MI]
(S)-(beta-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
EINECS 207-878-6
(2S)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
CHEBI:27826
DTXSID90198142
(2S)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
(S)-4-hydroxymandelonitrile-beta-D-glucoside
(S)-p-Hydroxymandelnitrile-beta-D-glucopyranoside
P-hydroxy-S-mandelonitrile-beta-D-glucopyranoside
Phyllanthoside?
Beta-D-glucopyranosyloxy-(S)-p-hydroxymandelonitrile
Phyllanthin?
.BETA.-D-GLUCOPYRANOSYLOXY-L-P-HYDROXYMANDELONITRILE
Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-4-hydroxy-, (alphaS)-
(2S)-2-(4-hydroxyphenyl)-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyacetonitrile
(2S)-dhurrin
DTXCID20120633
(2R)-alpha-(beta-D-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile dihydrate
(S)-4-Hydroxymandelonitrile b-D-glucoside
(S)-alpha-Cyano-p-hydroxybenzyl glucoside
(S)-4-Hydroxymandelonitrile I2-D-glucoside
BETA-D-GLUCOPYRANOSYLOXY-L-P-HYDROXYMANDELONITRILE
(S)-(b-D-Glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
(AlphaS)-a-(b-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
(AlphaS)-I+--(I2-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
(r)-p-hydroxymandelonitrile-d-glucopyranoside
499-20-7
C14H17NO7
(alphaS)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
SCHEMBL50174
Dhurrin, >=95% (HPLC)
1e55
HY-N8433
MSK158578
4-Hydroxymandelonitrile-?-D-glucoside
AKOS040760368
FD71615
1ST158578
CS-0144166
NS00031982
C05143
Q908811
(.ALPHA.S)-.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-4-HYDROXYBENZENEACETONITRILE
(2s)-2-(4-hydroxyphenyl)-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]acetonitrile
- Zintchem AAA, Ndongo JT, et al. (2014). Biological studies on nitrogen-containing compounds from Campylospermum oliverianum and Campylospermum sulcatum (Ochnaceae).. International Journal of Pharmacy and Pharmaceutical Sciences, 2014, 6, 252-256. [View]
- El Hawary S.S, Abubaker M, et al. (2022). Phytochemical constituents and anti-tyrosinase activity of Macadamia integrifolia leaves extract. Natural product research,2022, 36(4), 1089-1094. [View] [PubMed]
Pubchem:
161355
Cas:
499-20-7
Zinc:
ZINC000004096638
Kegg Ligand:
C05143
Chebi:
27826
Nmrshiftdb2:
60025950
Metabolights:
MTBLC27826
Comptox:
DTXSID90198142
CPRiL:
150362
SMILES: c1ccccc1COC2CCCCO2
Level: 1
Mol. Weight: 311.29 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 311.29 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 311.29 g/mol
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -5.43
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.050
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.24
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.500
- Plasma Protein Binding
- 60.56
- 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
- 8.800
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.140
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.580
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.100
- 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
- -3.460
- Rat (Acute)
- 2.470
- Rat (Chronic Oral)
- 3.320
- Fathead Minnow
- 4.030
- 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
- 426.390
- Hydration Free Energy
- -15.370
- Log(D) at pH=7.4
- -0.790
- Log(P)
- -1.07
- Log S
- -1.8
- Log(Vapor Pressure)
- -10.62
- Melting Point
- 157.68
- pKa Acid
- 5.24
- pKa Basic
- 4.53
| 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 | 0.9497 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8583 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8500 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8205 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8164 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8157 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7904 |
| Oxygen-insensitive NAD(P)H nitroreductase | P38489 | NFSB_ECOLI | Escherichia coli | 4 | 0.7792 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7720 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7688 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7685 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7680 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7523 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7303 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7281 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7262 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7254 |
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.7251 |
| Orotidine 5'-phosphate decarboxylase | O26232 | PYRF_METTH | Methanothermobacter thermautotrophicus | 3 | 0.7233 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7190 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7169 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7140 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7103 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7034 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7020 |
| Virulence sensor histidine kinase PhoQ | P0DM80 | PHOQ_SALTY | Salmonella typhimurium | 3 | 0.7015 |