NP-MRD: Showing NP-Card for methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate (NP0238293)

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Record Information

Version

2.0

Created at

2022-09-06 21:39:49 UTC

Updated at

2022-09-06 21:39:49 UTC

NP-MRD ID

NP0238293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate

Description

ROSELLISIN belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate is found in Macrophoma commelinae. methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate was first documented in 2020 (PMID: 32180845). Based on a literature review very few articles have been published on ROSELLISIN.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    5.9782    0.3384   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7166    0.1473   -0.0071 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304   -0.5770    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726   -1.2323    1.7482 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6401   -0.5938    1.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    0.1432    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4293    0.3273    0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260    1.5941    0.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0148    2.0813    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584    3.3308    0.8000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287    1.2188    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4998    1.9003    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9991    2.4425    1.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012   -0.0943    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9845   -0.8484   -0.1262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7943   -1.1128   -1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624   -0.5529    0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795   -2.0076   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163   -2.5713   -0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1329    1.4835   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -0.0568   -1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8240    0.0208    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1557   -1.1937    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    0.6976   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0746    3.0147   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039    1.6428   -0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8705    1.9951    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6111   -0.3152   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2977   -1.2015   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3641   -2.1021   -1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1147   -2.4550    0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689   -2.1498   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853   -3.3142    0.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7 17  2  0
 17 18  1  0
 18 19  1  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 11  2  0
 11 12  1  0
 12 13  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 16 28  1  0
 16 29  1  0
 16 30  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
M  END


  Mrv1652309062223392D          

 19 19  0  0  0  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
  7 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\C1=C(CO)C(OC)=C(CO)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O7/c1-17-10(15)4-3-9-7(5-13)11(18-2)8(6-14)12(16)19-9/h3-4,13-14H,5-6H2,1-2H3/b4-3+

> <INCHI_KEY>
UWAPCCUFQCTXOV-ONEGZZNKSA-N

> <FORMULA>
C12H14O7

> <MOLECULAR_WEIGHT>
270.237

> <EXACT_MASS>
270.073952791

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.15536894542139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2E)-3-[3,5-bis(hydroxymethyl)-4-methoxy-2-oxo-2H-pyran-6-yl]prop-2-enoate

> <JCHEM_LOGP>
-1.080913879333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.15025075809043

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.533738586951095

> <JCHEM_PKA_STRONGEST_BASIC>
-2.836937943782286

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
67.2454

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄O₇

Average Mass

270.2370 Da

Monoisotopic Mass

270.07395 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\C1=C(CO)C(OC)=C(CO)C(=O)O1

InChI Identifier

InChI=1S/C12H14O7/c1-17-10(15)4-3-9-7(5-13)11(18-2)8(6-14)12(16)19-9/h3-4,13-14H,5-6H2,1-2H3/b4-3+

InChI Key

UWAPCCUFQCTXOV-ONEGZZNKSA-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
Macrophoma commelinae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Alkyl aryl ether
Fatty acid ester
Pyranone
Fatty acyl
Heteroaromatic compound
Methyl ester
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Aromatic alcohol
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

4513677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5358551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nakashima KI, Tomida J, Hirai T, Kawamura Y, Inoue M: Absolute configurations of talaromycones A and B, alpha-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211. Beilstein J Org Chem. 2020 Feb 28;16:290-296. doi: 10.3762/bjoc.16.28. eCollection 2020. [PubMed:32180845 ]
LOTUS database [Link]

Showing NP-Card for methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate (NP0238293)

MOL for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

3D MOL for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

3D SDF for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

3D-SDF for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

PDB for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

3D PDB for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

SMILES for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

INCHI for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

Structure for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)

3D Structure for NP0238293 (methyl (2e)-3-[3,5-bis(hydroxymethyl)-4-methoxy-6-oxopyran-2-yl]prop-2-enoate)