NP-MRD: Showing NP-Card for Salirepin (NP0140208)

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Record Information

Version

2.0

Created at

2022-06-29 20:51:07 UTC

Updated at

2022-06-29 20:51:07 UTC

NP-MRD ID

NP0140208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Salirepin

Description

Salirepin 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. Salirepin is found in Idesia polycarpa and Itoa orientalis. Salirepin was first documented in 2007 (PMID: 17987500). Based on a literature review a small amount of articles have been published on salirepin (PMID: 35862808) (PMID: 32098786) (PMID: 24632218) (PMID: 17566912).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8996    0.7874    2.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375    0.6028    2.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623    0.2477    0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2517    0.1357    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952   -0.1923   -0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7973   -0.3033   -1.4629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007   -0.4037   -1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955   -0.2898   -1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8560    0.0376    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135    0.1688    0.5826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6325    0.0146    0.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3395    1.2076    0.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034    1.1491   -0.4194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6530    1.6481    0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3998    2.9837    0.9214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -0.1598   -0.9573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6966   -0.2219   -2.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6062   -1.3629   -0.2082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6495   -2.0365    0.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928   -1.0191    0.7350 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7387   -2.1245    1.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3979   -0.0114    3.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386   -0.1811    2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1890    1.5819    2.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1115    0.3006    0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2832   -1.2090   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543   -0.6619   -2.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2437   -0.4602   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5424   -0.2502   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.8931   -1.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    1.0026    1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6620    1.6434    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6343    3.0627    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1725   -0.1598   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1173    0.6065   -2.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749   -2.0914   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -2.7144   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195   -0.5845    1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5532   -2.6363    0.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
 11 20  1  0
 20 21  1  0
 20 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 13  1  0
  8  9  1  0
 15 33  1  0
 14 31  1  0
 14 32  1  0
 13 30  1  6
 11 29  1  6
  2 23  1  0
  2 24  1  0
  1 22  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 20 38  1  1
 21 39  1  0
 18 36  1  6
 19 37  1  0
 16 34  1  6
 17 35  1  0
M  END


  Mrv1652306292222512D          

 21 22  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 14 19  1  6  0  0  0
 13 20  1  1  0  0  0
 12 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0140208

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O8/c14-4-6-3-7(16)1-2-8(6)20-13-12(19)11(18)10(17)9(5-15)21-13/h1-3,9-19H,4-5H2/t9-,10-,11+,12-,13-/m1/s1

> <INCHI_KEY>
NPNFZOGKIFFKGT-UJPOAAIJSA-N

> <FORMULA>
C13H18O8

> <MOLECULAR_WEIGHT>
302.279

> <EXACT_MASS>
302.10016754

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.99002228592194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-[4-hydroxy-2-(hydroxymethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.62

> <JCHEM_LOGP>
-1.6693026879999997

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200330425657498

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.6772250945595

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9711410130191416

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
68.98010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-[4-hydroxy-2-(hydroxymethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14                                                            
CONECT   20   13                                                            
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈O₈

Average Mass

302.2790 Da

Monoisotopic Mass

302.10017 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H18O8/c14-4-6-3-7(16)1-2-8(6)20-13-12(19)11(18)10(17)9(5-15)21-13/h1-3,9-19H,4-5H2/t9-,10-,11+,12-,13-/m1/s1

InChI Key

NPNFZOGKIFFKGT-UJPOAAIJSA-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
Idesia polycarpa	LOTUS Database	35616633
Itoa orientalis	LOTUS Database	35616633

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

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Benzyl alcohol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Aromatic alcohol
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17614327

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16681676

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mosaddik A, Forster PI, Waterman PG: Three new 3-benzylbenzofuran-2-one derivatives from Homalium brachybotrys (Flacourtiaceae/Salicaceae s. l.). Nat Prod Res. 2007 Nov;21(13):1191-8. doi: 10.1080/14786410601130679. [PubMed:17987500 ]
Dove NC, Carrell AA, Engle NL, Klingeman DM, Rodriguez M, Wahl T, Tschaplinski TJ, Muchero W, Schadt CW, Cregger MA: Relationships between Sphaerulina musiva Infection and the Populus Microbiome and Metabolome. mSystems. 2022 Aug 30;7(4):e0012022. doi: 10.1128/msystems.00120-22. Epub 2022 Jul 18. [PubMed:35862808 ]
Lackus ND, Muller A, Krober TDU, Reichelt M, Schmidt A, Nakamura Y, Paetz C, Luck K, Lindroth RL, Constabel CP, Unsicker SB, Gershenzon J, Kollner TG: The Occurrence of Sulfated Salicinoids in Poplar and Their Formation by Sulfotransferase1. Plant Physiol. 2020 May;183(1):137-151. doi: 10.1104/pp.19.01447. Epub 2020 Feb 25. [PubMed:32098786 ]
Stepanova EV, Belyanin ML, Filimonov VD: Synthesis of acyl derivatives of salicin, salirepin, and arbutin. Carbohydr Res. 2014 Mar 31;388:105-11. doi: 10.1016/j.carres.2014.02.014. Epub 2014 Feb 20. [PubMed:24632218 ]
Ahmad VU, Rashid MA, Abbasi MA, Rasool N, Zubair M: New salirepin derivatives from Symplocos racemosa. J Asian Nat Prod Res. 2007 Apr-Aug;9(3-5):209-15. doi: 10.1080/10286020500531993. [PubMed:17566912 ]

Showing NP-Card for Salirepin (NP0140208)

MOL for NP0140208 (Salirepin)

3D MOL for NP0140208 (Salirepin)

3D SDF for NP0140208 (Salirepin)

3D-SDF for NP0140208 (Salirepin)

PDB for NP0140208 (Salirepin)

3D PDB for NP0140208 (Salirepin)

SMILES for NP0140208 (Salirepin)

INCHI for NP0140208 (Salirepin)

Structure for NP0140208 (Salirepin)

3D Structure for NP0140208 (Salirepin)