NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate (NP0200419)

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Record Information

Version

2.0

Created at

2022-09-04 19:15:37 UTC

Updated at

2022-09-04 19:15:37 UTC

NP-MRD ID

NP0200419

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate

Description

3,4,5-Trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1H-pyrrole-3-carboxylate belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. 3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate is found in Streptomyces griseoviridis. 3,4,5-Trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1H-pyrrole-3-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.3603   -1.1214    2.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -0.4837    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9821    0.0235    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8566    0.4935   -0.6516 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010    0.3041   -1.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717    0.6918   -2.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677   -0.3194   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634   -0.6909   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427   -1.8411   -0.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600    0.1879    0.1294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8805   -0.2213   -0.0092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4986    0.7076   -0.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8349    0.4005   -1.0730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3897    1.2827   -2.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5500    0.5541    0.2570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9274    0.4348    0.1045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9971   -0.5586    1.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6956   -0.6792    2.3291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264   -0.2420    1.3600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9071   -1.2563    2.0855 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6982   -1.9969    2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2501   -1.4194    2.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7526   -0.3949    2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8899    0.0569    1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155    0.9457   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -0.0723   -2.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4787    1.6456   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    0.7671   -3.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998   -1.2350   -0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9033   -0.6761   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5976    1.5393   -2.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    0.7039   -2.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8156    2.2251   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403    1.5239    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2908    1.3143   -0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822   -1.4903    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6691   -0.5926    2.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391    0.7302    1.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1390   -1.2411    3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 11 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 13  1  0
  2  7  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 13 30  1  6
 11 29  1  6
  6 26  1  0
  6 27  1  0
  6 28  1  0
  4 25  1  0
  3 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 19 38  1  1
 20 39  1  0
 17 36  1  6
 18 37  1  0
 15 34  1  1
 16 35  1  0
M  END


  Mrv1533004251502502D          

 20 21  0  0  0  0            999 V2000
    0.1067    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5846    3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492    2.2581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888    3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    7.2402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    8.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  2  0  0  0  0
  6  8  1  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
 12 13  1  0  0  0  0
  8 13  2  0  0  0  0
 13 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0200419

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC(=O)C2=C(C)NC=C2C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO6/c1-5-4-14-6(2)8(5)12(18)20-13-11(17)10(16)9(15)7(3)19-13/h4,7,9-11,13-17H,1-3H3

> <INCHI_KEY>
MQMFQDCHKXSJCD-UHFFFAOYSA-N

> <FORMULA>
C13H19NO6

> <MOLECULAR_WEIGHT>
285.296

> <EXACT_MASS>
285.121237336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.17384415429286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1H-pyrrole-3-carboxylate

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
0.4025374223333343

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.259410269489745

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20830476578808

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122030207354516

> <JCHEM_POLAR_SURFACE_AREA>
112.01

> <JCHEM_REFRACTIVITY>
69.1514

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1H-pyrrole-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       0.199  13.515   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.134  12.745   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.134  11.205   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.468  10.435   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.468   8.895   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.802   8.125   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.136   8.895   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.556   5.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.091   6.156   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.032   4.215   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -4.572   4.215   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -5.048   5.680   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.512   6.156   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.802  11.205   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.136  10.435   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.802  12.745   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.136  13.515   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.468  13.515   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.468  15.055   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    4   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1H-pyrrole-3-carboxylic acid	Generator

Chemical Formula

C₁₃H₁₉NO₆

Average Mass

285.2960 Da

Monoisotopic Mass

285.12124 Da

IUPAC Name

3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1H-pyrrole-3-carboxylate

Traditional Name

3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1H-pyrrole-3-carboxylate

CAS Registry Number

Not Available

SMILES

CC1OC(OC(=O)C2=C(C)NC=C2C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C13H19NO6/c1-5-4-14-6(2)8(5)12(18)20-13-11(17)10(16)9(15)7(3)19-13/h4,7,9-11,13-17H,1-3H3

InChI Key

MQMFQDCHKXSJCD-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 griseoviridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Pyrrole-3-carboxylic acid or derivatives
Oxane
Substituted pyrrole
Pyrrole
Vinylogous amide
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organic nitrogen 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	0.06	ALOGPS
logP	0.4	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.01 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.15 m³·mol⁻¹	ChemAxon
Polarizability	28.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

85168601

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate (NP0200419)

MOL for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

3D MOL for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

3D SDF for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

3D-SDF for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

PDB for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

3D PDB for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

SMILES for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

INCHI for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

Structure for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)

3D Structure for NP0200419 (3,4,5-trihydroxy-6-methyloxan-2-yl 2,4-dimethyl-1h-pyrrole-3-carboxylate)