NP-MRD: Showing NP-Card for 11,13-Dihydrotaraxinic acid glucosyl ester (NP0336300)

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Record Information

Version

2.0

Created at

2024-09-11 05:36:33 UTC

Updated at

2024-09-11 05:36:33 UTC

NP-MRD ID

NP0336300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11,13-Dihydrotaraxinic acid glucosyl ester

Description

11,13-Dihydrotaraxinic acid glucosyl ester belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. Based on a literature review very few articles have been published on 11,13-Dihydrotaraxinic acid glucosyl ester.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262308082D          

 30 32  0  0  0  0            999 V2000
   -3.7420    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4564   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4564   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0275   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0275   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130   -1.3848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5986   -0.9723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5986   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1415   -2.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210   -2.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9855   -1.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0275    0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420    1.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1785   -1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085   -2.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695    2.3278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8840    2.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5985    2.3278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5985    1.5027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8840    1.0902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1696    1.5028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5449    1.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841    0.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130    1.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130    2.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8840    3.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5985    3.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
  9  8  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
  4 15  1  0  0  0  0
 14 27  1  0  0  0  0
 14 16  2  0  0  0  0
 13 17  1  0  0  0  0
 12 18  2  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 23 26  1  6  0  0  0
 22 27  1  1  0  0  0
 21 28  1  6  0  0  0
 20 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END


  Mrv2104 05262308082D          

 30 32  0  0  0  0            999 V2000
   -3.7420    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4564   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4564   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0275   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0275   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130   -1.3848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5986   -0.9723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5986   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1415   -2.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210   -2.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9855   -1.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0275    0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7420    1.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1785   -1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085   -2.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695    2.3278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8840    2.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5985    2.3278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5985    1.5027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8840    1.0902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1696    1.5028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5449    1.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8841    0.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130    1.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130    2.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8840    3.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5985    3.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
  9  8  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
  4 15  1  0  0  0  0
 14 27  1  0  0  0  0
 14 16  2  0  0  0  0
 13 17  1  0  0  0  0
 12 18  2  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 23 26  1  6  0  0  0
 22 27  1  1  0  0  0
 21 28  1  6  0  0  0
 20 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1[C@@H]2CCC(=CCC\C(C)=C\[C@H]2OC1=O)C(=O)O[C@@H]1[C@@H](O)[C@H](O)O[C@H](CO)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1/C21H30O9/c1-10-4-3-5-12(6-7-13-11(2)19(25)28-14(13)8-10)20(26)30-18-16(23)15(9-22)29-21(27)17(18)24/h5,8,11,13-18,21-24,27H,3-4,6-7,9H2,1-2H3/b10-8+,12-5+/t11?,13-,14+,15+,16+,17+,18-,21+/s2

> <INCHI_KEY>
GHCVBVCIPFPICQ-VDWYTDPHNA-N

> <FORMULA>
C21H30O9

> <MOLECULAR_WEIGHT>
426.462

> <EXACT_MASS>
426.188982546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.3796421962485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_LOGP>
0.8314697813333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.83490774497365

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.30192743122407

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810986861448026

> <JCHEM_POLAR_SURFACE_AREA>
142.75000000000003

> <JCHEM_REFRACTIVITY>
104.29139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -6.985   0.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.319  -0.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.319  -1.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.985  -2.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.651  -1.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.651  -0.275   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.318   0.495   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.318  -2.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.984  -1.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.984  -0.275   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.997  -4.091   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.466  -4.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.840  -2.846   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.651   1.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.985  -4.125   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.985   2.035   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.333  -2.525   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.696  -5.586   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.316   4.345   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.650   5.115   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.984   4.345   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.984   2.805   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.650   2.035   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.317   2.805   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.017   2.035   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.650   0.495   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.318   2.035   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.318   5.115   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.650   6.655   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.984   7.425   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    8                                                       
CONECT    6    1    7   14                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   11                                                  
CONECT    9   10   13    8                                                  
CONECT   10    7    9                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13    9   12   17                                                  
CONECT   14    6   27   16                                                  
CONECT   15    4                                                            
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18   12                                                            
CONECT   19   20   24                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   19   23   25                                                  
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   14   22                                                       
CONECT   28   21                                                            
CONECT   29   20   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
11,13-Dihydrotaraxinate glucosyl ester	Generator

Chemical Formula

C₂₁H₃₀O₉

Average Mass

426.4620 Da

Monoisotopic Mass

426.18898 Da

IUPAC Name

(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

Not Available

SMILES

CC1[C@@H]2CCC(=CCC\C(C)=C\[C@H]2OC1=O)C(=O)O[C@@H]1[C@@H](O)[C@H](O)O[C@H](CO)[C@H]1O

InChI Identifier

InChI=1/C21H30O9/c1-10-4-3-5-12(6-7-13-11(2)19(25)28-14(13)8-10)20(26)30-18-16(23)15(9-22)29-21(27)17(18)24/h5,8,11,13-18,21-24,27H,3-4,6-7,9H2,1-2H3/b10-8+,12-5+/t11?,13-,14+,15+,16+,17+,18-,21+/s2

InChI Key

GHCVBVCIPFPICQ-VDWYTDPHNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as saccharolipids. These are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Germacranolide
Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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
logP	0.83	ChemAxon
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.29 m³·mol⁻¹	ChemAxon
Polarizability	42.38 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 11,13-Dihydrotaraxinic acid glucosyl ester (NP0336300)

MOL for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D MOL for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D SDF for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D-SDF for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

PDB for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D PDB for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

SMILES for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

INCHI for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

Structure for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D Structure for NP0336300 (11,13-Dihydrotaraxinic acid glucosyl ester)