NP-MRD: Showing NP-Card for Salsaside A (NP0044198)

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Record Information

Version

1.0

Created at

2021-11-12 23:56:36 UTC

Updated at

2021-11-26 17:46:32 UTC

NP-MRD ID

NP0044198

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Salsaside A

Description

Salsaside A belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Salsaside A is found in Cistanche salsa. It was first documented in 2007 (Li Lei et al.). Based on a literature review very few articles have been published on Salsaside A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652311132100562D          

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  -10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  6  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 13 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 11 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 33 36  1  0  0  0  0
 32 37  1  0  0  0  0
 10 38  1  6  0  0  0
  5 39  1  1  0  0  0
  4 40  1  1  0  0  0
  3 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044198

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)O[C@@H](OCC3=CC=CC=C3)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O13/c1-14-21(32)23(34)24(35)28(39-14)41-26-22(33)19(40-27(25(26)36)38-12-16-5-3-2-4-6-16)13-37-20(31)10-8-15-7-9-17(29)18(30)11-15/h2-11,14,19,21-30,32-36H,12-13H2,1H3/b10-8+/t14-,19+,21-,22+,23+,24+,25+,26-,27+,28-/m0/s1

> <INCHI_KEY>
YAGRMWUXYGBWOX-FFFXCZKYSA-N

> <FORMULA>
C28H34O13

> <MOLECULAR_WEIGHT>
578.567

> <EXACT_MASS>
578.199941155

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.777427677444344

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6R)-6-(benzyloxy)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
1.1378947986666674

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.863653703360606

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207845120918806

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826089745888

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
139.68630000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6R)-6-(benzyloxy)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0     -13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -20.005  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -17.338 -16.170   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5   40                                                  
CONECT    5    4    6   39                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   38                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   11   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   33                                                            
CONECT   37   32                                                            
CONECT   38   10                                                            
CONECT   39    5                                                            
CONECT   40    4                                                            
CONECT   41    3                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₁₃

Average Mass

578.5670 Da

Monoisotopic Mass

578.19994 Da

IUPAC Name

[(2R,3R,4S,5R,6R)-6-(benzyloxy)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3R,4S,5R,6R)-6-(benzyloxy)-3,5-dihydroxy-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)O[C@@H](OCC3=CC=CC=C3)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C28H34O13/c1-14-21(32)23(34)24(35)28(39-14)41-26-22(33)19(40-27(25(26)36)38-12-16-5-3-2-4-6-16)13-37-20(31)10-8-15-7-9-17(29)18(30)11-15/h2-11,14,19,21-30,32-36H,12-13H2,1H3/b10-8+/t14-,19+,21-,22+,23+,24+,25+,26-,27+,28-/m0/s1

InChI Key

YAGRMWUXYGBWOX-FFFXCZKYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	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
Cistanche salsa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Polyol
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
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
logP	0.51	ALOGPS
logP	1.14	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	139.69 m³·mol⁻¹	ChemAxon
Polarizability	56.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

28283897

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102403914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li Lei et al. (2007). New Glycosides from Cistanche salsa. DOI: 10.1002/hlca.200790024. Helvetica.

Showing NP-Card for Salsaside A (NP0044198)

MOL for NP0044198 (Salsaside A)

3D MOL for NP0044198 (Salsaside A)

3D SDF for NP0044198 (Salsaside A)

3D-SDF for NP0044198 (Salsaside A)

PDB for NP0044198 (Salsaside A)

3D PDB for NP0044198 (Salsaside A)

SMILES for NP0044198 (Salsaside A)

INCHI for NP0044198 (Salsaside A)

Structure for NP0044198 (Salsaside A)

3D Structure for NP0044198 (Salsaside A)