NP-MRD: Showing NP-Card for Mexicanin E (NP0051929)

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Record Information

Version

2.0

Created at

2022-04-27 23:07:58 UTC

Updated at

2022-04-27 23:07:59 UTC

NP-MRD ID

NP0051929

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mexicanin E

Description

Mexicanin E belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Mexicanin E is found in Helenium mexicanum and Helenium microcephalum. Based on a literature review very few articles have been published on Mexicanin E.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.8122    0.5582   -0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914   -0.3326    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0688   -1.7706    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734   -2.4139    0.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -2.3268    0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8122   -1.3634    0.3398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1627   -1.3713   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.6478   -0.5487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4984   -1.6880   -0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4141    0.3480    0.5350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7115    1.0941    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389    2.3414    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300    2.5573   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309    3.5251   -0.7245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111    1.4248    0.4622 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8682    1.0814   -0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5148   -0.0600    0.5120 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5871    1.6193   -0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222    0.2498   -0.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537   -1.6964    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -0.9959   -1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -2.4630   -1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -0.1744   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0185   -2.3895    0.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3668   -1.2561    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7522   -2.2887   -1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055   -0.1849    1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020    0.6982    0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    3.0926    0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    1.7195    1.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5568    1.9672   -0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7869    0.9360   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158    0.2103    1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 17  1  0
 17 16  1  0
 16 15  1  0
 15 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 10  8  1  0
 17  6  1  0
 13 15  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
  8 23  1  6
  7 21  1  0
  7 22  1  0
  6 20  1  1
  1 18  1  0
  1 19  1  0
 17 33  1  1
 16 31  1  0
 16 32  1  0
 15 30  1  1
 10 27  1  1
 11 28  1  0
 12 29  1  0
M  END


  Mrv1652304282201072D          

 17 19  0  0  1  0            999 V2000
    3.4890    2.3296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3054    1.5253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5621    1.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    1.5253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6352    2.3296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1496    2.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    2.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3326    3.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136    2.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    1.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    0.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.4036    0.0000 C   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  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  5  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  6  0  0  0
 12 13  2  0  0  0  0
  2 14  1  6  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  1 17  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051929

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2C[C@@H]2[C@H]1C=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c1-7-5-13-10(8(2)14(16)17-13)6-11-9(7)3-4-12(11)15/h3-4,7,9-11,13H,2,5-6H2,1H3/t7-,9+,10-,11-,13-/m1/s1

> <INCHI_KEY>
GQOWVFHMXITOCQ-QWRHMFJTSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.279

> <EXACT_MASS>
232.109944375

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.44483624610504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4aR,7aR,8R,9aR)-8-methyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-2,5-dione

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
2.480146959333333

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.36802596574826

> <JCHEM_PKA_STRONGEST_BASIC>
-4.942457937138222

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
63.70540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mexicanin E

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.513   4.349   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.170   2.847   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.783   2.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.395   2.847   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.052   4.349   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.013   5.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.553   5.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.221   6.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.519   4.487   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.913   3.071   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.588   2.728   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.073   2.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.935   0.524   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.492   2.057   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.630   0.524   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.652   3.071   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.047   4.487   0.000  0.00  0.00           C+0
CONECT    1    2    7   17                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    1                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₃

Average Mass

232.2790 Da

Monoisotopic Mass

232.10994 Da

IUPAC Name

(3aR,4aR,7aR,8R,9aR)-8-methyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-2,5-dione

Traditional Name

mexicanin E

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2C[C@@H]2[C@H]1C=CC2=O

InChI Identifier

InChI=1S/C14H16O3/c1-7-5-13-10(8(2)14(16)17-13)6-11-9(7)3-4-12(11)15/h3-4,7,9-11,13H,2,5-6H2,1H3/t7-,9+,10-,11-,13-/m1/s1

InChI Key

GQOWVFHMXITOCQ-QWRHMFJTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Helenium mexicanum	Plant	KNApSAcK
Helenium microcephalum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

gamma-lactone (CHEBI:6914 )
pseudoguaianolide (C09503 )

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	0.7	ALOGPS
logP	2.48	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	18.37	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	63.71 m³·mol⁻¹	ChemAxon
Polarizability	24.44 Å³	ChemAxon
Number of Rings	3	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

C00003325

Chemspider ID

20868

KEGG Compound ID

C09503

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22226

PDB ID

Not Available

ChEBI ID

6914

Good Scents ID

Not Available

References

General References

Showing NP-Card for Mexicanin E (NP0051929)

MOL for NP0051929 (Mexicanin E)

3D MOL for NP0051929 (Mexicanin E)

3D SDF for NP0051929 (Mexicanin E)

3D-SDF for NP0051929 (Mexicanin E)

PDB for NP0051929 (Mexicanin E)

3D PDB for NP0051929 (Mexicanin E)

SMILES for NP0051929 (Mexicanin E)

INCHI for NP0051929 (Mexicanin E)

Structure for NP0051929 (Mexicanin E)

3D Structure for NP0051929 (Mexicanin E)