NP-MRD: Showing NP-Card for methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate (NP0207711)

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Record Information

Version

2.0

Created at

2022-09-05 04:25:51 UTC

Updated at

2022-09-05 04:25:51 UTC

NP-MRD ID

NP0207711

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate

Description

Oleracerin F 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. methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate is found in Portulaca oleracea. Based on a literature review very few articles have been published on Oleracerin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206252D          

 39 42  0  0  1  0            999 V2000
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   -0.5837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052206252D          

 39 42  0  0  1  0            999 V2000
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  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 31 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207711

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1CC2=CC(O)=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2N1C(=O)\C=C\C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H29NO12/c1-36-18-7-12(3-5-16(18)29)4-6-21(31)27-14-10-19(17(30)9-13(14)8-15(27)25(35)37-2)38-26-24(34)23(33)22(32)20(11-28)39-26/h3-7,9-10,15,20,22-24,26,28-30,32-34H,8,11H2,1-2H3/b6-4+/t15-,20+,22+,23-,24+,26+/m0/s1

> <INCHI_KEY>
KNUYHEQHOCPQAW-AFBSOZDYSA-N

> <FORMULA>
C26H29NO12

> <MOLECULAR_WEIGHT>
547.513

> <EXACT_MASS>
547.168975378

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.17143798817907

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-5-hydroxy-1-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-indole-2-carboxylate

> <JCHEM_LOGP>
-0.02625893933333301

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.063687751451935

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.415711275695118

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2470403806026487

> <JCHEM_POLAR_SURFACE_AREA>
195.68

> <JCHEM_REFRACTIVITY>
132.91199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-5-hydroxy-1-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.090  -2.637   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.090   0.031   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.259   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259   1.777   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.592   2.547   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.592  -0.533   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.926   0.237   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.592  -2.073   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.926  -2.843   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.259  -4.383   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.821  -7.903   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.358  -7.079   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.376  -5.294   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.406  -4.150   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -4.930  -2.685   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24   11   25                                                       
CONECT   25   24    7   26                                                  
CONECT   26   25    5   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   31                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₉NO₁₂

Average Mass

547.5130 Da

Monoisotopic Mass

547.16898 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1CC2=CC(O)=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2N1C(=O)\C=C\C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C26H29NO12/c1-36-18-7-12(3-5-16(18)29)4-6-21(31)27-14-10-19(17(30)9-13(14)8-15(27)25(35)37-2)38-26-24(34)23(33)22(32)20(11-28)39-26/h3-7,9-10,15,20,22-24,26,28-30,32-34H,8,11H2,1-2H3/b6-4+/t15-,20+,22+,23-,24+,26+/m0/s1

InChI Key

KNUYHEQHOCPQAW-AFBSOZDYSA-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
Portulaca oleracea	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
Alpha-amino acid ester
Indolecarboxylic acid derivative
Cinnamic acid or derivatives
Hexose monosaccharide
Indolecarboxylic acid
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Methoxyphenol
Alpha-amino acid or derivatives
Indole or derivatives
Phenol ether
Phenoxy compound
Styrene
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Tertiary carboxylic acid amide
Methyl ester
Secondary alcohol
Carboxylic acid ester
Carboxamide group
Polyol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Azacycle
Ether
Oxacycle
Carboxylic acid derivative
Organic nitrogen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organonitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52914108

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate (NP0207711)

MOL for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

3D MOL for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

3D SDF for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

3D-SDF for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

PDB for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

3D PDB for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

SMILES for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

INCHI for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

Structure for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)

3D Structure for NP0207711 (methyl (2s)-5-hydroxy-1-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindole-2-carboxylate)