NP-MRD: Showing NP-Card for 8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C (NP0139849)

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Record Information

Version

2.0

Created at

2022-06-29 20:13:31 UTC

Updated at

2022-06-29 20:13:31 UTC

NP-MRD ID

NP0139849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C

Description

93395-31-4 Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C is found in Crepis capillaris, Crepis mollis and Crepis pyrenaica. Based on a literature review very few articles have been published on 93395-31-4.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292222132D          

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M  END

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 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 29 36  1  0  0  0  0
 28 37  1  0  0  0  0
  4 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C(C)(O)C(=O)OC1CC(=C)C2CC(OC3OC(CO)C(O)C(O)C3O)C(=C)C2C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-9-6-15(37-25(33)26(5,34)12(4)28)18-11(3)23(32)38-22(18)17-10(2)14(7-13(9)17)35-24-21(31)20(30)19(29)16(8-27)36-24/h13-22,24,27,29-31,34H,1-3,6-8H2,4-5H3

> <INCHI_KEY>
ZFRBQIGYWHKJRW-UHFFFAOYSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.71341163885849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-2-methyl-3-oxobutanoate

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-0.8909664909999986

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.228268502588815

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.869781177534819

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836843960926

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
126.56909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,9-trimethylidene-2-oxo-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-4-yl 2-hydroxy-2-methyl-3-oxobutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       6.808   7.512   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.578   5.989   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.782   5.029   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.145   5.426   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.582   6.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.507   5.824   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.665   3.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.813  -1.598   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.018  -2.558   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.451  -1.995   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.681  -0.473   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.477   0.488   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.043  -0.075   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.706   2.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.140   2.573   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      16.114   0.090   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      15.655  -2.956   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      12.788  -4.081   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.707   3.993   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   38                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   13   19                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19    9   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19                                                       
CONECT   26   15   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   37                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30                                                            
CONECT   36   29                                                            
CONECT   37   28                                                            
CONECT   38    4                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)C(C)(O)C(=O)OC1CC(=C)C2CC(OC3OC(CO)C(O)C(O)C3O)C(=C)C2C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C26H34O12/c1-9-6-15(37-25(33)26(5,34)12(4)28)18-11(3)23(32)38-22(18)17-10(2)14(7-13(9)17)35-24-21(31)20(30)19(29)16(8-27)36-24/h13-22,24,27,29-31,34H,1-3,6-8H2,4-5H3

InChI Key

ZFRBQIGYWHKJRW-UHFFFAOYSA-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
Crepis capillaris (L.) Wallr.	LOTUS Database	35616633
Crepis mollis	LOTUS Database	35616633
Crepis pyrenaica (L.) Greuter	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-keto acid
Fatty acid ester
Acyloin
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Keto acid
Monosaccharide
Oxane
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Alpha-hydroxy ketone
Enoate ester
Lactone
Ketone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Oxacycle
Acetal
Organooxygen compound
Carbonyl group
Organic oxygen compound
Primary alcohol
Organic oxide
Alcohol
Hydrocarbon derivative
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

131863733

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C (NP0139849)

MOL for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

3D MOL for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

3D SDF for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

3D-SDF for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

PDB for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

3D PDB for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

SMILES for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

INCHI for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

Structure for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)

3D Structure for NP0139849 (8beta-(2-Hydroxy-2-methyl-3-oxobutyryloxy)glucozaluzanin C)