NP-MRD: Showing NP-Card for (2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid (NP0240638)

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Record Information

Version

2.0

Created at

2022-09-07 00:30:42 UTC

Updated at

2022-09-07 00:30:42 UTC

NP-MRD ID

NP0240638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid

Description

Methoxyhygromycin A 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. (2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid is found in Streptomyces hygroscopicus. Based on a literature review very few articles have been published on Methoxyhygromycin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202302D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072202302D          

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 33 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0240638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1[C@@H](O)[C@H](O)C(N=C(O)C(\C)=C\C2=CC=C(O[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)C(C)=O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO12/c1-8(22(33)24-13-14(27)16(29)21(34-3)17(30)15(13)28)6-10-4-5-12(11(26)7-10)35-23-19(32)18(31)20(36-23)9(2)25/h4-7,13-21,23,26-32H,1-3H3,(H,24,33)/b8-6+/t13?,14-,15+,16+,17-,18-,19-,20+,21?,23+/m0/s1

> <INCHI_KEY>
LFHKNMMEABAJBZ-HYNQVQEHSA-N

> <FORMULA>
C23H31NO12

> <MOLECULAR_WEIGHT>
513.496

> <EXACT_MASS>
513.184625442

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.71164002084138

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(4-{[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-[(2R,3S,5R,6S)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid

> <JCHEM_LOGP>
-1.4472954853333326

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.690160774250138

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.538370767394286

> <JCHEM_PKA_STRONGEST_BASIC>
2.204854022943417

> <JCHEM_POLAR_SURFACE_AREA>
218.95999999999995

> <JCHEM_REFRACTIVITY>
120.48469999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(4-{[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-[(2R,3S,5R,6S)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.869  15.055   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.535  15.825   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.201  15.055   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.868  15.825   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.868  17.365   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.534  15.055   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.200  15.825   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.534  13.515   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.200  12.745   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.200  11.205   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.534  10.435   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.867  10.435   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.867   8.895   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.533  11.205   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.199  10.435   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.134  11.205   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.468  10.435   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.468   8.895   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.802   8.125   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.802   6.585   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.556   5.680   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.032   4.215   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.127   2.969   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.595   3.130   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.753   1.562   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.572   4.215   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.477   2.969   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.048   5.680   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.512   6.156   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.134   8.125   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.134   6.585   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.199   8.895   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.868  12.745   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.868  11.205   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.201  13.515   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -9.535  12.745   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   29                                                  
CONECT   29   28                                                            
CONECT   30   18   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   15                                                       
CONECT   33    8   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₁NO₁₂

Average Mass

513.4960 Da

Monoisotopic Mass

513.18463 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1[C@@H](O)[C@H](O)C(N=C(O)C(\C)=C\C2=CC=C(O[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)C(C)=O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H31NO12/c1-8(22(33)24-13-14(27)16(29)21(34-3)17(30)15(13)28)6-10-4-5-12(11(26)7-10)35-23-19(32)18(31)20(36-23)9(2)25/h4-7,13-21,23,26-32H,1-3H3,(H,24,33)/b8-6+/t13?,14-,15+,16+,17-,18-,19-,20+,21?,23+/m0/s1

InChI Key

LFHKNMMEABAJBZ-HYNQVQEHSA-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
Streptomyces hygroscopicus	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
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid amide
O-glycosyl compound
Pentose monosaccharide
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexanol
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Cyclitol or derivatives
Tetrahydrofuran
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Ketone
Carboxamide group
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Alcohol
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

8273489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10097955

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid (NP0240638)

MOL for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

3D MOL for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

3D SDF for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

3D-SDF for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

PDB for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

3D PDB for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

SMILES for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

INCHI for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

Structure for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)

3D Structure for NP0240638 ((2e)-3-(4-{[(2s,3s,4s,5s)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-[(2r,3s,5r,6s)-2,3,5,6-tetrahydroxy-4-methoxycyclohexyl]prop-2-enimidic acid)