NP-MRD: Showing NP-Card for Roseoside (NP0139238)

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Record Information

Version

2.0

Created at

2022-06-29 19:45:23 UTC

Updated at

2022-06-29 19:45:23 UTC

NP-MRD ID

NP0139238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Roseoside

Description

Roseoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Roseoside is found in Alangium platanifolium, Antidesma membranaceum, Astragalus complanatus, Baccharis dracunculifolia, Betula pendula, Brachystemma calycinum, Psydrax subcordata, Cistus laurifolius, Clerodendrum indicum, Codonopsis clematidea, Conyza aegyptiaca, Crocus sativus, Croton insularis, Cydonia oblonga, Elaeocarpus japonicus, Epimedium grandiflorum, Eriobotrya japonica, Euphorbia maculata, Hemerocallis fulva, Isatis tinctoria, Juniperus phoenicea, Ligusticum lucidum, Litsea glutinosa, Macaranga tanarius, Mallotus peltatus, Malus domestica, Malus sylvestris, Melaleuca quinquenervia, Morus alba, Ophiorrhiza liukiuensis, Oreocnide rubescens, Persicaria hydropiper, Picris hieracioides, Pinus sylvestris, Prunus domestica, Prunus ssiori, Pyracantha coccinea, Ruellia patula, Ruellia tuberosa, Salvia nemorosa, Thujopsis dolabrata, Trachelospermum jasminoides, Tribulus parvispinus, Trifolium alexandrinum, Vitis vinifera and Wahlenbergia marginata. Roseoside was first documented in 2018 (PMID: 29356892). Based on a literature review a significant number of articles have been published on Roseoside (PMID: 30875889) (PMID: 31496281) (PMID: 30633652) (PMID: 33634716) (PMID: 30556957) (PMID: 29368956).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221452D          

 27 28  0  0  1  0            999 V2000
    0.3272   -3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -4.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1018   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1018   -6.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163   -4.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1018   -3.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4891   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -1.4594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2637   -1.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0020   -0.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -0.0314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2139   -0.0026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6012    0.7259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1640    1.4255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3395    1.3967    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9522    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9023    2.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2896    2.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5513    2.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4257    0.7547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -0.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -3.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2534   -3.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  6  0  0  0
  8 25  1  6  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
   -3.6016    1.0785   -1.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7223    0.9290   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9448    0.9249    0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0856    0.7792    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1548    1.1354    2.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175    0.2164    2.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -0.3442    1.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5572   -1.5206    0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350   -0.8030    2.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000    0.7862    0.5029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5218    1.9542    1.2596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967    0.5497   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086   -0.2725   -1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497   -0.4306   -1.7372 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1441   -0.2642   -3.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1482    0.5003   -1.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1889   -0.1103   -0.5103 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1869    0.2393    0.8249 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618   -0.1892    1.5416 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9349    1.0141    2.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0433    0.5843    2.9343 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2560   -1.0173    0.8315 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8763   -2.3738    0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5512   -0.6311   -0.5718 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8459   -0.1458   -0.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100    0.2961   -1.1218 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4991    0.1302   -2.5129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9630    0.1364   -2.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953    1.3783   -2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2873    1.9009   -2.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8203    1.0234   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522    0.9883    3.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975   -0.6270    3.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977   -1.2936   -0.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467   -2.3915    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4542   -1.9336    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -0.0314    2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185   -1.6848    1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583   -1.1537    3.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    2.7371    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4126    1.0878    0.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9166   -0.8275   -1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6583   -1.4447   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959    0.4651   -3.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227    0.1504   -3.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053   -1.2259   -3.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014   -1.2177   -0.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8646   -0.7972    2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537    1.5122    2.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2030    1.7721    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8379    0.9981    2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2278   -0.9573    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727   -2.4828    1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996   -1.5720   -1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9604    0.1044   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.3372   -0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233    1.0338   -2.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  1
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 26 17  1  0
  7 10  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 14 43  1  6
 17 47  1  1
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  1
 23 53  1  0
 24 54  1  6
 25 55  1  0
 26 56  1  6
 27 57  1  0
 13 42  1  0
 12 41  1  0
 11 40  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
M  END


  Mrv1652306292221452D          

 27 28  0  0  1  0            999 V2000
    0.3272   -3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -4.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1018   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1018   -6.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163   -4.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1018   -3.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4891   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -1.4594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2637   -1.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0020   -0.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -0.0314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2139   -0.0026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6012    0.7259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1640    1.4255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3395    1.3967    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9522    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9023    2.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2896    2.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5513    2.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4257    0.7547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -0.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408   -3.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2534   -3.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  6  0  0  0
  8 25  1  6  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h5-7,11,13-17,20,22-25H,8-9H2,1-4H3/b6-5+/t11-,13-,14-,15+,16-,17-,19-/m1/s1

> <INCHI_KEY>
SWYRVCGNMNAFEK-MHXFFUGFSA-N

> <FORMULA>
C19H30O8

> <MOLECULAR_WEIGHT>
386.441

> <EXACT_MASS>
386.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.49962071292672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E,3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-1-en-1-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
-0.3518366106666663

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.017420338021633

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.183449896937358

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083681947405

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
97.3405

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E,3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-1-en-1-yl]cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       0.611  -6.750   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.723  -7.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.723  -9.060   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.057  -9.830   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.057 -11.370   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.390  -9.060   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.390  -7.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.057  -6.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.780  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.964  -4.084   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.687  -2.724   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.226  -2.671   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.870  -1.418   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.593  -0.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.133  -0.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.856   1.355   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.039   2.661   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.500   2.607   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.777   1.247   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.684   3.913   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.407   5.273   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.762   4.021   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.395   1.409   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.949  -1.311   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.929  -7.466   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.206  -6.214   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   26   27                                             
CONECT    8    7    2    9   25                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
CONECT   25    8                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₃₀O₈

Average Mass

386.4410 Da

Monoisotopic Mass

386.19407 Da

IUPAC Name

(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E,3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-1-en-1-yl]cyclohex-2-en-1-one

Traditional Name

(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E,3R)-3-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-1-en-1-yl]cyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

C[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C19H30O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h5-7,11,13-17,20,22-25H,8-9H2,1-4H3/b6-5+/t11-,13-,14-,15+,16-,17-,19-/m1/s1

InChI Key

SWYRVCGNMNAFEK-MHXFFUGFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alangium platanifolium	LOTUS Database	35616633
Antidesma membranaceum	LOTUS Database	35616633
Astragalus complanatus	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Brachystemma calycinum	LOTUS Database	35616633
Canthium subcordatum	LOTUS Database	35616633
Cistus laurifolius	LOTUS Database	35616633
Clerodendrum indicum	LOTUS Database	35616633
Codonopsis clematidea	LOTUS Database	35616633
Conyza aegyptiaca	LOTUS Database	35616633
Crocus sativus	LOTUS Database	35616633
Croton insularis	LOTUS Database	35616633
Cydonia oblonga	LOTUS Database	35616633
Elaeocarpus japonicus	LOTUS Database	35616633
Epimedium grandiflorum	LOTUS Database	35616633
Eriobotrya japonica	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Hemerocallis fulva	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633
Juniperus phoenicea	LOTUS Database	35616633
Ligusticum lucidum	LOTUS Database	35616633
Litsea glutinosa	LOTUS Database	35616633
Macaranga tanarius	LOTUS Database	35616633
Mallotus peltatus	LOTUS Database	35616633
Malus domestica	LOTUS Database	35616633
Malus sylvestris	LOTUS Database	35616633
Melaleuca quinquenervia	LOTUS Database	35616633
Morus alba	LOTUS Database	35616633
Ophiorrhiza liukiuensis	LOTUS Database	35616633
Oreocnide rubescens	LOTUS Database	35616633
Persicaria hydropiper	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Prunus ssiori	LOTUS Database	35616633
Pyracantha coccinea	LOTUS Database	35616633
Ruellia patula	LOTUS Database	35616633
Ruellia tuberosa	LOTUS Database	35616633
Salvia nemorosa	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633
Trachelospermum jasminoides	LOTUS Database	35616633
Tribulus parvispinus	LOTUS Database	35616633
Trifolium alexandrinum	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Wahlenbergia marginata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Monosaccharide
Oxane
Tertiary alcohol
Cyclic ketone
Ketone
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.3	ALOGPS
logP	-0.35	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.34 m³·mol⁻¹	ChemAxon
Polarizability	40.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029329

Chemspider ID

8105695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9930064

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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Vu LTN, Anh LT, Cuc NT, Nhiem NX, Tai BH, Van Kiem P, Litaudon M, Thach TD, Van Minh C, Mai HDT, Van Cuong P: Prenylated flavonoids and other constituents from Macaranga indica. Nat Prod Res. 2021 Jul;35(13):2123-2130. doi: 10.1080/14786419.2019.1662007. Epub 2019 Sep 9. [PubMed:31496281 ]
Gupta MK, Vadde R: Insights into the structure-function relationship of both wild and mutant zinc transporter ZnT8 in human: a computational structural biology approach. J Biomol Struct Dyn. 2020 Jan;38(1):137-151. doi: 10.1080/07391102.2019.1567391. Epub 2019 Jan 31. [PubMed:30633652 ]
Huong PTT, Tai BH, Nhiem NX, Cuong NX, Quang TH, Thu VK, Yen PH, Kiem PV: Saurobacciosides A - C: three new glycosides from Sauropus bacciformis with their cytotoxic activity. Nat Prod Res. 2022 Mar;36(6):1476-1484. doi: 10.1080/14786419.2021.1892670. Epub 2021 Feb 26. [PubMed:33634716 ]
Revoltella S, Rainer B, Waltenberger B, Pagitz K, Schwaiger S, Stuppner H: HPTLC Autography Based Screening and Isolation of Mushroom Tyrosinase Inhibitors of European Plant Species. Chem Biodivers. 2019 Mar;16(3):e1800541. doi: 10.1002/cbdv.201800541. Epub 2019 Feb 14. [PubMed:30556957 ]
Shao JH, Chen J, Xu XQ, Zhao CC, Dong ZL, Liu WY, Shen J: Chemical constituents and biological activities of Viburnum macrocephalum f. keteleeri. Nat Prod Res. 2019 Jun;33(11):1612-1616. doi: 10.1080/14786419.2018.1428593. Epub 2018 Jan 25. [PubMed:29368956 ]
Cuc NT, Yen DTH, Yen PH, Hang DTT, Tai BH, Seo Y, Namkung W, Kim SH, Cuong PV, Kiem PV, Nhiem NX, Ngoc TM: Dihydrostilbene glycosides from Camellia sinensis var. assamica and their cytotoxic activity. Nat Prod Res. 2022 Aug;36(15):3931-3937. doi: 10.1080/14786419.2021.1900844. Epub 2021 Mar 22. [PubMed:33749416 ]
Lee YR, Park JH, Castaneda Molina R, Nam YH, Lee YG, Hong BN, Baek NI, Kang TH: Skin depigmenting action of silkworm (Bombyx mori L.) droppings in zebrafish. Arch Dermatol Res. 2018 Apr;310(3):245-253. doi: 10.1007/s00403-018-1804-1. Epub 2018 Jan 22. [PubMed:29356892 ]
Ata FK, Ercan F, Azarkan SY: In vivo, in vitro and Molecular Modelling Analysis of Isoquercetin, Roseoside, Coreximine, Anonaine, and Arianacin Molecules. Curr Comput Aided Drug Des. 2022;18(3):168-184. doi: 10.2174/1573409918666220509213313. [PubMed:35538817 ]
Liang SM, Zhang F, Zou YN, Kuca K, Wu QS: Metabolomics Analysis Reveals Drought Responses of Trifoliate Orange by Arbuscular Mycorrhizal Fungi With a Focus on Terpenoid Profile. Front Plant Sci. 2021 Oct 6;12:740524. doi: 10.3389/fpls.2021.740524. eCollection 2021. [PubMed:34691116 ]
Wang YF, He RJ, Li DP, Huang YL: Three new compounds from the leaves of Castanopsis tibetana Hance. Nat Prod Res. 2022 Oct;36(19):4906-4910. doi: 10.1080/14786419.2021.1910690. Epub 2021 Apr 24. [PubMed:33896288 ]
Morcol TB, Wysocki K, Sankaran RP, Matthews PD, Kennelly EJ: UPLC-QTof-MS(E) Metabolomics Reveals Changes in Leaf Primary and Secondary Metabolism of Hop (Humulus lupulus L.) Plants under Drought Stress. J Agric Food Chem. 2020 Dec 9;68(49):14698-14708. doi: 10.1021/acs.jafc.0c05987. Epub 2020 Nov 25. [PubMed:33236890 ]
Yang H, Sun W, Ma P, Yao C, Fan Y, Li S, Yuan J, Zhang Z, Li X, Lin M, Hou Q: Multiple Components Rapidly Screened from Perilla Leaves Attenuate Asthma Airway Inflammation by Synergistic Targeting on Syk. J Inflamm Res. 2020 Nov 13;13:897-911. doi: 10.2147/JIR.S281393. eCollection 2020. [PubMed:33223845 ]
Ebada SS, Al-Jawabri NA, Youssef FS, El-Kashef DH, Knedel TO, Albohy A, Korinek M, Hwang TL, Chen BH, Lin GH, Lin CY, Aldalaien SM, Disi AM, Janiak C, Proksch P: Anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities of phytochemicals from the Jordanian hawksbeard: identification, structure-activity relationships, molecular modeling and impact on its folk medicinal uses. RSC Adv. 2020 Oct 15;10(62):38128-38141. doi: 10.1039/d0ra04876c. eCollection 2020 Oct 12. [PubMed:35515148 ]
Rahim A, Mostofa MG, Sadik MG, Rahman MAA, Khalil MI, Tsukahara T, Nakagawa-Goto K, Alam AK: The anticancer activity of two glycosides from the leaves of Leea aequata L. Nat Prod Res. 2021 Dec;35(24):5867-5871. doi: 10.1080/14786419.2020.1798661. Epub 2020 Jul 27. [PubMed:32713195 ]
Placines C, Castaneda-Loaiza V, Joao Rodrigues M, Pereira CG, Stefanucci A, Mollica A, Zengin G, Llorent-Martinez EJ, Castilho PC, Custodio AL: Phenolic Profile, Toxicity, Enzyme Inhibition, In Silico Studies, and Antioxidant Properties of Cakile maritima Scop. (Brassicaceae) from Southern Portugal. Plants (Basel). 2020 Jan 22;9(2):142. doi: 10.3390/plants9020142. [PubMed:31979182 ]
Zhang Y, Liu J, Guo Z, Li X, Wang M: Chemical constituents from Urtica fissa stem and their inhibitory effects on alpha-glucosidase activity. Nat Prod Res. 2021 Sep;35(18):3011-3017. doi: 10.1080/14786419.2019.1684279. Epub 2019 Nov 1. [PubMed:31674849 ]
Hong EY, Kim TY, Hong GU, Kang H, Lee JY, Park JY, Kim SC, Kim YH, Chung MH, Kwon YI, Ro JY: Inhibitory Effects of Roseoside and Icariside E4 Isolated from a Natural Product Mixture (No-ap) on the Expression of Angiotensin II Receptor 1 and Oxidative Stress in Angiotensin II-Stimulated H9C2 Cells. Molecules. 2019 Jan 23;24(3):414. doi: 10.3390/molecules24030414. [PubMed:30678135 ]
Pacifico S, Piccolella S, Nocera P, Tranquillo E, Dal Poggetto F, Catauro M: New insights into phenol and polyphenol composition of Stevia rebaudiana leaves. J Pharm Biomed Anal. 2019 Jan 30;163:45-57. doi: 10.1016/j.jpba.2018.09.046. Epub 2018 Sep 28. [PubMed:30286435 ]

Showing NP-Card for Roseoside (NP0139238)

MOL for NP0139238 (Roseoside)

3D MOL for NP0139238 (Roseoside)

3D SDF for NP0139238 (Roseoside)

3D-SDF for NP0139238 (Roseoside)

PDB for NP0139238 (Roseoside)

3D PDB for NP0139238 (Roseoside)

SMILES for NP0139238 (Roseoside)

INCHI for NP0139238 (Roseoside)

Structure for NP0139238 (Roseoside)

3D Structure for NP0139238 (Roseoside)