NP-MRD: Showing NP-Card for Arbutin (NP0002713)

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Record Information

Version

1.0

Created at

2020-11-23 19:38:35 UTC

Updated at

2024-04-19 09:28:06 UTC

NP-MRD ID

NP0002713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arbutin

Provided By

BMRB

Description

Arbutin, also known as ursin or uvasol, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Arbutin exists in all living organisms, ranging from bacteria to humans. Arbutin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Arbutin is found in Aesculus californica, Antennaria microphylla, Arbutus andrachne, Arbutus unedo, Arctostaphylos canescens, Arctostaphylos patula, Betula pendula, Betula platyphylla, Breynia fruticosa, Breynia vitis-idaea, Broussonetia papyrifera, Calluna vulgaris, Camellia sinensis, Cephalanthus occidentalis, Cotoneaster symondsii, Cuscuta chinensis, Galium mollugo, Gerbera piloselloides, Grevillea robusta, Halocarpus biformis, Huperzia serrata, Hylotelephium ewersii, Juniperus communis, Klasea radiata, Mutisia acerosa, Mutisia acuminata, Mutisia oligodon, Mutisia orbignyana, Myrothamnus flabellifolia, Myrsine seguinii, Nelumbo nucifera, Onobrychis arenaria, Onobrychis bobrovii, Onobrychis meschetica, Onobrychis radiata, Onobrychis viciifolia, Paederia foetida, Phedimus kamtschaticus, Picrasma quassioides, Pyrus bourgaeana, Pyrus calleryana, Rauvolfia serpentina, Rhodiola coccinea, Rhodiola kirilowii, Rhodiola sacra, Rhododendron luteum, Salix acmophylla , Salvia rhyacophila, Hylotelephium telephium, Semiarundinaria fastuosa, Senecio mairetianus, Solanum tuberosum, Sorbaria sorbifolia, Stratiotes aloides, Thymus vulgaris, Turnera diffusa, Turnera subulata, Vaccinium arctostaphylos, Vaccinium dunalianum, Vaccinium erythrocarpum, Vaccinium pallidum, Viburnum dilatatum, Viburnum phlebotrichum, Viburnum rhytidophyllum, Viburnum wrightii, Viola arvensis, Zanthoxylum bungeanum and Zanthoxylum piperitum. It was first documented in 1998 (PMID: 9518563). Based on a literature review a small amount of articles have been published on Arbutin (PMID: 23438684) (PMID: 17984079) (PMID: 12807345) (PMID: 15287073).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    1.8950   -4.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2142   -2.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334   -1.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346   -1.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7726    1.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015    0.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7401    1.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -0.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882   -0.6101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9496   -1.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5207   -0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    1.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575    2.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0660    1.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    0.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4443   -0.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -4.5694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -2.9666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7486   -2.3282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9214   -1.7506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8496   -0.7115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920    3.2339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8497    2.3212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8074   -2.0758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2688   -2.6287    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -1.7159    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496    2.0430    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478    3.9491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4358    2.9007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852    3.3363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213    1.0039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -0.4666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  6
  2 22  1  0
  3 23  1  6
  5 24  1  6
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  1
 15 31  1  0
 16 32  1  6
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END

NP0002713
     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.3048    1.1708   -2.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    1.2554   -1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.1435   -1.1655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2685   -1.0645   -1.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238   -1.0465   -0.0728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3765    0.0650    0.0252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492    0.1661    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781    1.4134    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    1.5691    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5385    0.4721    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361    0.5646    0.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9830   -0.7736   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5873   -0.9148   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -1.2903    1.1548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0912   -2.3931    0.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495   -0.1188    1.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5688    1.0584    1.6037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779   -0.0567    0.0843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9889   -1.1335    0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.0519   -3.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    1.8763   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    1.6540   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -0.4491   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994   -1.9577   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7543    2.2946    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    2.5352    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4649    0.5199    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770   -1.6813   -0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1863   -1.9031   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7155   -1.5249    2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487   -2.9230    0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980   -0.3586    2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.6702    2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871    0.8758    0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -1.4797   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  6
  5 24  1  6
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  1
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END


     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    1.8950   -4.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2142   -2.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334   -1.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346   -1.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7726    1.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015    0.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7401    1.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -0.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882   -0.6101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9496   -1.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5207   -0.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    1.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575    2.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    1.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0660    1.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    0.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4443   -0.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661   -4.5694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6798   -2.9666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7486   -2.3282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9214   -1.7506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8496   -0.7115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920    3.2339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8497    2.3212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8074   -2.0758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2688   -2.6287    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -1.7159    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496    2.0430    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478    3.9491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4358    2.9007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852    3.3363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213    1.0039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -0.4666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  6
  2 22  1  0
  3 23  1  6
  5 24  1  6
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  1
 15 31  1  0
 16 32  1  6
 17 33  1  0
 18 34  1  1
 19 35  1  0
M  END
> <DATABASE_ID>
NP0002713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
BJRNKVDFDLYUGJ-RMPHRYRLSA-N

> <FORMULA>
C12H16O7

> <MOLECULAR_WEIGHT>
272.2512

> <EXACT_MASS>
272.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.87568345161489

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-0.9019529206666663

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201773728176159

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.820455894002922

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923436865826

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
62.164199999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.91e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-arbutin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002713
     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.3048    1.1708   -2.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    1.2554   -1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.1435   -1.1655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2685   -1.0645   -1.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238   -1.0465   -0.0728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3765    0.0650    0.0252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492    0.1661    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781    1.4134    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    1.5691    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5385    0.4721    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361    0.5646    0.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9830   -0.7736   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5873   -0.9148   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -1.2903    1.1548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0912   -2.3931    0.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495   -0.1188    1.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5688    1.0584    1.6037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779   -0.0567    0.0843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9889   -1.1335    0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.0519   -3.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    1.8763   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    1.6540   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -0.4491   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994   -1.9577   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7543    2.2946    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    2.5352    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4649    0.5199    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770   -1.6813   -0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1863   -1.9031   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7155   -1.5249    2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487   -2.9230    0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980   -0.3586    2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.6702    2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871    0.8758    0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -1.4797   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  6
  5 24  1  6
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  1
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8664.9558663.060   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8670.2948666.140   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8662.2918667.680   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8660.9578668.450   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8662.2918661.520   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8659.6198663.060   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8659.6198666.140   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8668.9598665.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.6268666.139   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.2928665.369   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.2928663.829   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.6268663.059   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.9598663.829   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.2898666.139   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.9558665.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.9558663.829   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.2898663.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.6228663.829   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8663.6228665.369   0.000  0.00  0.00           O+0
CONECT    1   11   18                                                       
CONECT    2    8                                                            
CONECT    3    4   14                                                       
CONECT    4    3                                                            
CONECT    5   17                                                            
CONECT    6   16                                                            
CONECT    7   15                                                            
CONECT    8    9   13    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    1                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   15   19    3                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    6                                                  
CONECT   17   16   18    5                                                  
CONECT   18   17   19    1                                                  
CONECT   19   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    NP0002713
HETATM    1  O1  UNL     1      -1.305   1.171  -2.852  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.812   1.255  -1.576  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.271  -0.144  -1.166  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.269  -1.065  -1.171  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.424  -1.047  -0.073  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.377   0.065   0.025  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.749   0.166   0.027  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.378   1.413   0.139  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.732   1.569   0.146  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.539   0.472   0.041  1.00  0.00           C  
HETATM   11  O4  UNL     1       5.936   0.565   0.042  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.983  -0.774  -0.071  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.587  -0.915  -0.077  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.290  -1.290   1.155  1.00  0.00           C  
HETATM   15  O5  UNL     1      -2.091  -2.393   0.856  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.250  -0.119   1.350  1.00  0.00           C  
HETATM   17  O6  UNL     1      -1.569   1.058   1.604  1.00  0.00           O  
HETATM   18  C12 UNL     1      -3.078  -0.057   0.084  1.00  0.00           C  
HETATM   19  O7  UNL     1      -3.989  -1.133   0.166  1.00  0.00           O  
HETATM   20  H1  UNL     1      -1.043   2.052  -3.217  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.749   1.876  -1.599  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.095   1.654  -0.847  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.987  -0.449  -1.986  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.199  -1.958  -0.160  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.754   2.295   0.223  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.214   2.535   0.232  1.00  0.00           H  
HETATM   27  H8  UNL     1       6.465   0.520   0.906  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.577  -1.681  -0.158  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.186  -1.903  -0.165  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.716  -1.525   2.049  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.749  -2.923   0.098  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.898  -0.359   2.199  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.218   1.670   2.076  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.687   0.876   0.035  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.190  -1.480  -0.742  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3   21   22
CONECT    3    4   18   23
CONECT    4    5
CONECT    5    6   14   24
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   12
CONECT   11   27
CONECT   12   13   13   28
CONECT   13   29
CONECT   14   15   16   30
CONECT   15   31
CONECT   16   17   18   32
CONECT   17   33
CONECT   18   19   34
CONECT   19   35
END

NP0002713
     RDKit          3D

35 36  0  0  0  0  0  0  0  0999 V2000
   -1.3048    1.1708   -2.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    1.2554   -1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.1435   -1.1655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2685   -1.0645   -1.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238   -1.0465   -0.0728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3765    0.0650    0.0252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492    0.1661    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781    1.4134    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    1.5691    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5385    0.4721    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361    0.5646    0.0417 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9830   -0.7736   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5873   -0.9148   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -1.2903    1.1548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0912   -2.3931    0.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495   -0.1188    1.3497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5688    1.0584    1.6037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779   -0.0567    0.0843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9889   -1.1335    0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    2.0519   -3.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7486    1.8763   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951    1.6540   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875   -0.4491   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994   -1.9577   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7543    2.2946    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    2.5352    0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4649    0.5199    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770   -1.6813   -0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1863   -1.9031   -0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7155   -1.5249    2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487   -2.9230    0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980   -0.3586    2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2181    1.6702    2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6871    0.8758    0.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1898   -1.4797   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  3  1  0
 13  7  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  6
  5 24  1  6
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  1
 15 31  1  0
 16 32  1  1
 17 33  1  0
 18 34  1  6
 19 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
Hydroquinone-O-beta-D-glucopyranoside	ChEBI
p-Hydroxyphenyl beta-D-glucopyranoside	ChEBI
p-Hydroxyphenyl beta-D-glucoside	ChEBI
Ursin	ChEBI
Uvasol	ChEBI
Hydroquinone-O-b-D-glucopyranoside	Generator
Hydroquinone-O-β-D-glucopyranoside	Generator
p-Hydroxyphenyl b-D-glucopyranoside	Generator
p-Hydroxyphenyl β-D-glucopyranoside	Generator
p-Hydroxyphenyl b-D-glucoside	Generator
p-Hydroxyphenyl β-D-glucoside	Generator
Arbutin	ChEBI
4-Hydroxyphenyl-b-glucopyranoside	Generator, HMDB
4-Hydroxyphenyl-β-glucopyranoside	Generator, HMDB
4-Hydroxyphenyl beta-D-glucopyranoside	PhytoBank, HMDB
4-Hydroxyphenyl β-D-glucopyranoside	PhytoBank, HMDB
Arbutine	PhytoBank, HMDB
Arbutoside	PhytoBank, HMDB
Arbutyne	PhytoBank, HMDB
Hydroquinone beta-D-glucopyranoside	PhytoBank, HMDB
Hydroquinone glucose	PhytoBank, HMDB
Hydroquinone β-D-glucopyranoside	PhytoBank, HMDB
beta-Arbutin	PhytoBank, HMDB
p-Arbutin	PhytoBank, HMDB
β-Arbutin	PhytoBank, HMDB

Chemical Formula

C₁₂H₁₆O₇

Average Mass

272.2512 Da

Monoisotopic Mass

272.08960 Da

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

Traditional Name

β-arbutin

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

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

InChI Key

BJRNKVDFDLYUGJ-RMPHRYRLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenosma caeruleum	KNApSAcK Database	22123792
Aesculus californica	LOTUS Database	35616633
Angelica furcijuga KITAGAWA	KNApSAcK Database	22123792
Antennaria microphylla	LOTUS Database	35616633
Arbutus andrachne L.	LOTUS Database	35616633
Arbutus unedo	LOTUS Database	35616633
Arctostaphylos canescens	LOTUS Database	35616633
Arctostaphylos patula	LOTUS Database	35616633
Arctostaphylos uva-ursi	KNApSAcK Database	22123792
Bergenia crassifolia	KNApSAcK Database	22123792
Betula pendula	LOTUS Database	35616633
Betula platyphylla	LOTUS Database	35616633
Breynia fruticosa	LOTUS Database	35616633
Breynia officinalis	KNApSAcK Database	22123792
Breynia vitis-idaea	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Calluna vulgaris	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Cephalanthus occidentalis	LOTUS Database	35616633
Cotoneaster simonsii	KNApSAcK Database	22123792
Cotoneaster symondsii	LOTUS Database	35616633
Cuscuta chinensis	LOTUS Database	35616633
Cydonia oblonga	FooDB	PHENOL EXPLORER
Galium mollugo	LOTUS Database	35616633
Gerbera piloselloides	LOTUS Database	35616633
Grevillea robusta	LOTUS Database	35616633
Halocarpus biformis	LOTUS Database	35616633
Huperzia serrata	LOTUS Database	35616633
Hylotelephium ewersii	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Klasea radiata	LOTUS Database	35616633
Malus pumila	FooDB	PHENOL EXPLORER
Mutisia acerosa	LOTUS Database	35616633
Mutisia acuminata	LOTUS Database	35616633
Mutisia oligodon	LOTUS Database	35616633
Mutisia orbignyana	LOTUS Database	35616633
Myrothamnus flabellifolia	LOTUS Database	35616633
Myrsine seguinii	LOTUS Database	35616633
Nelumbo nucifera	LOTUS Database	35616633
Onobrychis arenaria	LOTUS Database	35616633
Onobrychis bobrovi	KNApSAcK Database	22123792
Onobrychis bobrovii	LOTUS Database	35616633
Onobrychis meschetica	LOTUS Database	35616633
Onobrychis radiata	LOTUS Database	35616633
Onobrychis viciifolia	LOTUS Database	35616633
Origanum majorana	KNApSAcK Database	22123792
Paederia foetida	LOTUS Database	35616633
Phedimus kamtschaticus	LOTUS Database	35616633
Picrasma quassioides	LOTUS Database	35616633
Pyrus bourgaeana	LOTUS Database	35616633
Pyrus communis	KNApSAcK Database	22123792
Pyrus kawakamii	LOTUS Database	35616633
Pyrus pyrifolia	FooDB	18778075
Rauvolfia serpentina	LOTUS Database	35616633
Rhodiola coccinea	LOTUS Database	35616633
Rhodiola kirilowii	LOTUS Database	35616633
Rhodiola sacra	LOTUS Database	35616633
Rhododendron ferrugineum	KNApSAcK Database	22123792
Rhododendron luteum	LOTUS Database	35616633
Rhododendron ponticum	KNApSAcK Database	22123792
Salix acmophylla	Plant	KNApSAcK
Salvia rhyacophila	LOTUS Database	35616633
Sedum takesimense Nakai	KNApSAcK Database	22123792
Sedum telephium	LOTUS Database	35616633
Semiarundinaria fastuosa	LOTUS Database	35616633
Senecio mairetianus	LOTUS Database	35616633
Solanum tuberosum	LOTUS Database	35616633
Sorbaria sorbifolia	LOTUS Database	35616633
Stratiotes aloides	LOTUS Database	35616633
Thymus vulgaris	LOTUS Database	35616633
Triticum	FooDB	PHYTOHUB
Turnera diffusa	LOTUS Database	35616633
Turnera subulata	Plant	KNApSAcK
Vaccinium arctostaphylos	LOTUS Database	35616633
Vaccinium dunalianum	LOTUS Database	35616633
Vaccinium erythrocarpum	LOTUS Database	35616633
Vaccinium myrtillus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vaccinium pallidum	LOTUS Database	35616633
Vaccinium vitis-idaea	KNApSAcK Database	22123792
Veronica turrilliana	KNApSAcK Database	22123792
Viburnum dilatatum	LOTUS Database	35616633
Viburnum phlebotrichum	LOTUS Database	35616633
Viburnum rhytidophyllum	LOTUS Database	35616633
Viburnum wrightii	LOTUS Database	35616633
Viola arvensis	LOTUS Database	35616633
Zanthoxylum bungeanum	LOTUS Database	35616633
Zanthoxylum piperitum	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	199.00 to 200.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	561.00 to 562.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	959100 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-1.350	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	-1.4	ALOGPS
logP	-0.9	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.16 m³·mol⁻¹	ChemAxon
Polarizability	25.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029943

DrugBank ID

DB11217

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

HYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE

BiGG ID

Not Available

Wikipedia Link

Arbutin

METLIN ID

Not Available

PubChem Compound

440936

PDB ID

Not Available

ChEBI ID

18305

Good Scents ID

rw1653821

References

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Siegers C, Bodinet C, Ali SS, Siegers CP: Bacterial deconjugation of arbutin by Escherichia coli. Phytomedicine. 2003;10 Suppl 4:58-60. doi: 10.1078/1433-187x-00301. [PubMed:12807345 ]
Hori I, Nihei K, Kubo I: Structural criteria for depigmenting mechanism of arbutin. Phytother Res. 2004 Jun;18(6):475-9. doi: 10.1002/ptr.1456. [PubMed:15287073 ]
Oliver AE, Hincha DK, Crowe LM, Crowe JH: Interactions of arbutin with dry and hydrated bilayers. Biochim Biophys Acta. 1998 Mar 6;1370(1):87-97. doi: 10.1016/s0005-2736(97)00246-0. [PubMed:9518563 ]

Showing NP-Card for Arbutin (NP0002713)

MOL for NP0002713 (Arbutin)

3D MOL for NP0002713 (Arbutin)

3D SDF for NP0002713 (Arbutin)

3D-SDF for NP0002713 (Arbutin)

PDB for NP0002713 (Arbutin)

3D PDB for NP0002713 (Arbutin)

SMILES for NP0002713 (Arbutin)

INCHI for NP0002713 (Arbutin)

Structure for NP0002713 (Arbutin)

3D Structure for NP0002713 (Arbutin)