NP-MRD: Showing NP-Card for 3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid (NP0310909)

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Record Information

Version

2.0

Created at

2022-09-11 06:32:57 UTC

Updated at

2022-09-11 06:32:57 UTC

NP-MRD ID

NP0310909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid

Description

3-(4-{[3,4-Dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid 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. 3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(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 3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112208322D          

 36 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112208322D          

 36 38  0  0  0  0            999 V2000
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 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 15 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0310909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(O)C(O)C(N=C(O)C(C)=CC2=CC=C(OC3OC(C(C)O)C(O)C3O)C(O)=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H33NO12/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/h4-7,9,13-21,23,25-32H,1-3H3,(H,24,33)

> <INCHI_KEY>
HGGFSJSFAIZTED-UHFFFAOYSA-N

> <FORMULA>
C23H33NO12

> <MOLECULAR_WEIGHT>
515.512

> <EXACT_MASS>
515.200275507

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.34222085886703

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid

> <JCHEM_LOGP>
-1.6806205213333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.690299891750632

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.5383739649598756

> <JCHEM_PKA_STRONGEST_BASIC>
2.2048575102232704

> <JCHEM_POLAR_SURFACE_AREA>
222.11999999999998

> <JCHEM_REFRACTIVITY>
121.48500000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-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

Value	Source
3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidate	Generator

Chemical Formula

C₂₃H₃₃NO₁₂

Average Mass

515.5120 Da

Monoisotopic Mass

515.20028 Da

IUPAC Name

3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid

Traditional Name

3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-N-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

COC1C(O)C(O)C(N=C(O)C(C)=CC2=CC=C(OC3OC(C(C)O)C(O)C3O)C(O)=C2)C(O)C1O

InChI Identifier

InChI=1S/C23H33NO12/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/h4-7,9,13-21,23,25-32H,1-3H3,(H,24,33)

InChI Key

HGGFSJSFAIZTED-UHFFFAOYSA-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 amide
Cinnamic acid or derivatives
O-glycosyl compound
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexanol
Monosaccharide
Cyclitol or derivatives
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tetrahydrofuran
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Dialkyl ether
Ether
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Organonitrogen 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	-1.7	ChemAxon
pKa (Strongest Acidic)	5.54	ChemAxon
pKa (Strongest Basic)	2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	222.12 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.48 m³·mol⁻¹	ChemAxon
Polarizability	52.34 Å³	ChemAxon
Number of Rings	3	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

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

76011779

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid (NP0310909)

MOL for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

3D MOL for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

3D SDF for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

3D-SDF for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

PDB for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

3D PDB for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

SMILES for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

INCHI for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

Structure for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)

3D Structure for NP0310909 (3-(4-{[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy}-3-hydroxyphenyl)-2-methyl-n-(2,3,5,6-tetrahydroxy-4-methoxycyclohexyl)prop-2-enimidic acid)