7OQ
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-oxidanylphenoxy)oxane-3,4,5-triol
Created: | 2021-10-08 |
Last modified: | 2022-03-09 |
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Chemical Details | |
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Formal Charge | 0 |
Atom Count | 35 |
Chiral Atom Count | 5 |
Bond Count | 36 |
Aromatic Bond Count | 6 |
Chemical Component Summary | |
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Name | (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-oxidanylphenoxy)oxane-3,4,5-triol |
Systematic Name (OpenEye OEToolkits) | (2~{R},3~{S},4~{S},5~{R},6~{S})-2-(hydroxymethyl)-6-(4-oxidanylphenoxy)oxane-3,4,5-triol |
Formula | C12 H16 O7 |
Molecular Weight | 272.251 |
Type | NON-POLYMER |
Chemical Descriptors | |||
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Type | Program | Version | Descriptor |
SMILES | CACTVS | 3.385 | OC[CH]1O[CH](Oc2ccc(O)cc2)[CH](O)[CH](O)[CH]1O |
SMILES | OpenEye OEToolkits | 2.0.7 | c1cc(ccc1O)OC2C(C(C(C(O2)CO)O)O)O |
Canonical SMILES | CACTVS | 3.385 | OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
Canonical SMILES | OpenEye OEToolkits | 2.0.7 | c1cc(ccc1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O |
InChI | InChI | 1.03 | InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1 |
InChIKey | InChI | 1.03 | BJRNKVDFDLYUGJ-RMPHRYRLSA-N |
Drug Info: DrugBank
DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank ID | DB11217 |
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Name | Arbutin |
Groups | approved |
Description | Extracted from the dried leaves of bearberry plant in the genus _Arctostaphylos_ and other plants commonly in the _Ericaceae_ family, arbutin is a beta-D-glucopyranoside of [DB09526]. It is found in foods, over-the-counter drugs, and herbal dietary supplements [F43]. Most commonly, it is an active ingredient in skincare and cosmetic products as a skin-lightening agent for the prevention of melanin formation in various skin conditions that involve cutaneous hyperpigmentation or hyperactive melanocyte function [A27248]. It has also been used as an anti-infective for the urinary system as well as a diuretic [F43]. Arbutin is available in both natural and synthetic forms; it can be synthesized from acetobromglucose and [DB09526] [F43]. Arbutin is a competitive inhibitor of tyrosinase (E.C.1.14.18.1) in melanocytes [A27248], and the inhibition of melanin synthesis at non-toxic concentrations was observed _in vitro_. Arbutin was shown to be less cytotoxic to melanocytes in culture compared to [DB09526] [A32942]. |
Synonyms |
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Brand Names |
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Indication | Indicated for over-the-counter use for epidermal hyperpigmentation in various skin conditions, such as melasma, freckles, and senile lentigines. |
Categories |
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CAS number | 497-76-7 |
Drug Targets
DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
Name | Target Sequence | Pharmacological Action | Actions |
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Tyrosinase | MLLAVLYCLLWSFQTSAGHFPRACVSSKNLMEKECCPPWSGDRSPCGQLS... | unknown | inhibitor |
Albumin | MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA... | unknown |
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison
T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS.
Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682
Related Resource References
Resource Name | Reference |
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PubChem | 440936 |
ChEMBL | CHEMBL232202 |
ChEBI | CHEBI:18305 |
CCDC/CSD | FUYJOZ, MIDSAW |