NP-MRD: Showing NP-Card for methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0236127)

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Record Information

Version

2.0

Created at

2022-09-06 18:56:58 UTC

Updated at

2022-09-06 18:56:58 UTC

NP-MRD ID

NP0236127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate

Description

Methyl (3aS,4S,5R,11aR)-10-(hydroxymethyl)-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate is found in Melampodium longicorne. Based on a literature review very few articles have been published on methyl (3aS,4S,5R,11aR)-10-(hydroxymethyl)-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220562D          

 34 35  0  0  1  0            999 V2000
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  6 34  1  0  0  0  0
M  END

     RDKit          3D

 68 69  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309062220562D          

 34 35  0  0  1  0            999 V2000
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 27 34  1  0  0  0  0
 34  2  1  1  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@H]1[C@@H](OC(=O)C(C)C)[C@@H]2[C@H](OC(=O)C2=C)\C=C(CO)/CC\C=C1\C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O9/c1-7-14(4)23(28)33-20-17(25(30)31-6)10-8-9-16(12-26)11-18-19(15(5)24(29)32-18)21(20)34-22(27)13(2)3/h10-11,13-14,18-21,26H,5,7-9,12H2,1-4,6H3/b16-11+,17-10+/t14-,18-,19+,20-,21+/m1/s1

> <INCHI_KEY>
ZAWIKRVIJVSVPK-MZQKJXCTSA-N

> <FORMULA>
C25H34O9

> <MOLECULAR_WEIGHT>
478.538

> <EXACT_MASS>
478.220282675

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.63899674541327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (3aS,4S,5R,11aR)-10-(hydroxymethyl)-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_LOGP>
3.6560212676666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.146344682724777

> <JCHEM_PKA_STRONGEST_BASIC>
-2.734788835776013

> <JCHEM_POLAR_SURFACE_AREA>
125.43

> <JCHEM_REFRACTIVITY>
122.29239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3aS,4S,5R,11aR)-10-(hydroxymethyl)-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <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       0.947   2.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.243   1.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.150  -0.101   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.148  -0.930   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.583  -0.665   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.562   0.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.100   0.593   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.810   1.959   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.349   2.028   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -7.177   0.730   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.982   3.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.692   4.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.863   5.922   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.325   5.854   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.496   7.152   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.042   7.084   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.206   8.519   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.378   9.817   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.615   4.487   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.330   5.336   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.901   4.809   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.141   3.111   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.627   5.176   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.240   7.034   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.710   4.809   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.995   5.658   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.443   3.189   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.905   3.121   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.076   4.419   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.786   5.786   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.462   4.351   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.291   5.649   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.172   2.984   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.733   1.823   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   19   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   27    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3as,4S,5R,11ar)-10-(hydroxymethyl)-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₄O₉

Average Mass

478.5380 Da

Monoisotopic Mass

478.22028 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@H]1[C@@H](OC(=O)C(C)C)[C@@H]2[C@H](OC(=O)C2=C)\C=C(CO)/CC\C=C1\C(=O)OC

InChI Identifier

InChI=1S/C25H34O9/c1-7-14(4)23(28)33-20-17(25(30)31-6)10-8-9-16(12-26)11-18-19(15(5)24(29)32-18)21(20)34-22(27)13(2)3/h10-11,13-14,18-21,26H,5,7-9,12H2,1-4,6H3/b16-11+,17-10+/t14-,18-,19+,20-,21+/m1/s1

InChI Key

ZAWIKRVIJVSVPK-MZQKJXCTSA-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
Melampodium longicorne	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Enoate ester
Methyl ester
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

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

162859370

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0236127)

MOL for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0236127 (methyl (3as,4s,5r,11ar)-10-(hydroxymethyl)-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-4-[(2-methylpropanoyl)oxy]-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)