NP-MRD: Showing NP-Card for 10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate (NP0172969)

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Record Information

Version

2.0

Created at

2022-09-03 10:01:38 UTC

Updated at

2022-09-03 10:01:38 UTC

NP-MRD ID

NP0172969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

Description

10-(Hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 4-(acetyloxy)-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. 10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate is found in Centaurea aspera. 10-(Hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161503382D          

 29 30  0  0  0  0            999 V2000
    3.3495    5.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0582    4.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441    4.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810    3.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897    3.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125    2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071    1.5358    0.0000 C   0  0  0  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
    4.8581    1.1649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.2594    0.0000 O   0  0  0  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  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
    5.9037   -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  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    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  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    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
    5.6722    1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 12 26  1  0  0  0  0
 20 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 29  1  0  0  0  0
M  END


  Mrv1533004161503382D          

 29 30  0  0  0  0            999 V2000
    3.3495    5.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0582    4.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441    4.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810    3.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897    3.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125    2.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071    1.5358    0.0000 C   0  0  0  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
    4.8581    1.1649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.2594    0.0000 O   0  0  0  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  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
    5.9037   -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  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    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  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298   -2.4271    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
    5.6722    1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 12 26  1  0  0  0  0
 20 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC=C(C)C(=O)OC1CC(C)=CCCC(CO)=CC2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O7/c1-13-6-5-7-17(12-23)11-19-20(15(3)22(26)29-19)18(10-13)28-21(25)14(2)8-9-27-16(4)24/h6,8,11,18-20,23H,3,5,7,9-10,12H2,1-2,4H3

> <INCHI_KEY>
GNIAWQVTXAZHNK-UHFFFAOYSA-N

> <FORMULA>
C22H28O7

> <MOLECULAR_WEIGHT>
404.459

> <EXACT_MASS>
404.183503242

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.33994537428572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.563525178333333

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.553664218729757

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.146328366916954

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7347884706510843

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
108.04780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.252   9.821   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.709   8.381   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.189   8.131   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.685   7.189   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.141   5.748   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.117   4.557   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   3.116   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.053   2.867   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       9.068   2.174   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.005   0.484   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.476  -1.649   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       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.917  -2.397   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.379  -2.326   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.259   0.006   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.331   1.544   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.389  -4.531   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.845  -5.971   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.588   2.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   12   20                                                  
CONECT   27   18   28                                                       
CONECT   28   27                                                            
CONECT   29   14                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
10-(Hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₈O₇

Average Mass

404.4590 Da

Monoisotopic Mass

404.18350 Da

IUPAC Name

10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

Traditional Name

10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC=C(C)C(=O)OC1CC(C)=CCCC(CO)=CC2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C22H28O7/c1-13-6-5-7-17(12-23)11-19-20(15(3)22(26)29-19)18(10-13)28-21(25)14(2)8-9-27-16(4)24/h6,8,11,18-20,23H,3,5,7,9-10,12H2,1-2,4H3

InChI Key

GNIAWQVTXAZHNK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Centaurea aspera	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
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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
logP	1.89	ALOGPS
logP	2.56	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.05 m³·mol⁻¹	ChemAxon
Polarizability	43.34 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

75069477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate (NP0172969)

MOL for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D MOL for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D SDF for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D-SDF for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

PDB for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D PDB for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

SMILES for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

INCHI for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

Structure for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)

3D Structure for NP0172969 (10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 4-(acetyloxy)-2-methylbut-2-enoate)