NP-MRD: Showing NP-Card for (3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate (NP0218732)

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Record Information

Version

2.0

Created at

2022-09-05 19:29:50 UTC

Updated at

2022-09-05 19:29:50 UTC

NP-MRD ID

NP0218732

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate

Description

(3AS,4R,6R,7S,10R,11aS)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate 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. (3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate is found in Helianthus annuus. Based on a literature review very few articles have been published on (3aS,4R,6R,7S,10R,11aS)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221292D          

 30 31  0  0  1  0            999 V2000
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3353    1.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722    1.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493   -1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5078   -1.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713   -1.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8820   -1.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4015   -2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -3.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -3.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6330   -4.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -4.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1558   -4.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699   -4.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30  2  1  1  0  0  0
  6 30  1  0  0  0  0
M  END


  Mrv1652309052221292D          

 30 31  0  0  1  0            999 V2000
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3353    1.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722    1.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9493   -1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5078   -1.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713   -1.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8820   -1.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4015   -2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -3.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384   -3.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6330   -4.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -4.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1558   -4.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699   -4.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30  2  1  1  0  0  0
  6 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218732

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O8/c1-7-12(2)20(25)30-17-10-22(4,28-6)18(27-5)9-15(24)14(11-23)8-16-19(17)13(3)21(26)29-16/h7,14,16-19,23H,3,8-11H2,1-2,4-6H3/b12-7-/t14-,16+,17-,18+,19+,22-/m1/s1

> <INCHI_KEY>
LOQBOYSPYWSYGO-AUBMJEJFSA-N

> <FORMULA>
C22H32O8

> <MOLECULAR_WEIGHT>
424.49

> <EXACT_MASS>
424.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.16334221301652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4R,6R,7S,10R,11aS)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.0364737833333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.272301055224528

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.133822071259708

> <JCHEM_PKA_STRONGEST_BASIC>
-2.662786412852663

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
108.66829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4R,6R,7S,10R,11aS)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.417  -3.528   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.379  -2.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.259   0.006   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.093   3.366   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.588   2.424   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.452  -2.840   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.972  -2.591   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.281  -2.684   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.466  -3.352   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.980  -3.637   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.350  -5.030   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.325  -6.221   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.845  -5.971   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.782  -7.662   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.262  -7.911   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.758  -8.853   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.277  -8.604   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.917  -2.397   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19   21                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   22    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
(3AS,4R,6R,7S,10R,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₃₂O₈

Average Mass

424.4900 Da

Monoisotopic Mass

424.20972 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H32O8/c1-7-12(2)20(25)30-17-10-22(4,28-6)18(27-5)9-15(24)14(11-23)8-16-19(17)13(3)21(26)29-16/h7,14,16-19,23H,3,8-11H2,1-2,4-6H3/b12-7-/t14-,16+,17-,18+,19+,22-/m1/s1

InChI Key

LOQBOYSPYWSYGO-AUBMJEJFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helianthus annuus	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
Fatty acid ester
Cyclitol or derivatives
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic ketone
Carboxylic acid ester
Lactone
Ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Alcohol
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

162871678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate (NP0218732)

MOL for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

PDB for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

Structure for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0218732 ((3as,4r,6r,7s,10r,11as)-10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2z)-2-methylbut-2-enoate)