NP-MRD: Showing NP-Card for 25-Acetylvulgaroside (NP0084781)

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Record Information

Version

2.0

Created at

2022-04-29 05:26:01 UTC

Updated at

2022-04-29 05:26:01 UTC

NP-MRD ID

NP0084781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

25-Acetylvulgaroside

Description

25-O-acetylvulgaroside belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position. 25-Acetylvulgaroside is found in Cydonia oblonga and Cydonia vulgaris . Based on a literature review very few articles have been published on 25-O-acetylvulgaroside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207262D          

 36 39  0  0  1  0            999 V2000
    4.3772    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292207262D          

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 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 19 22  1  6  0  0  0
 19 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 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
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 27 34  2  0  0  0  0
 34 35  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@]3(C)[C@@H](CC(O)C4=CC(=O)OC4OC(C)=O)[C@](O)(CO)CC[C@]3([H])[C@@]1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O7/c1-16(29)33-23-17(13-22(31)34-23)18(30)14-21-26(5)11-7-19-24(2,3)9-6-10-25(19,4)20(26)8-12-27(21,32)15-28/h13,18-21,23,28,30,32H,6-12,14-15H2,1-5H3/t18?,19-,20+,21+,23?,25-,26+,27+/m0/s1

> <INCHI_KEY>
QNZZHRCSGTYEAW-REXWJDRESA-N

> <FORMULA>
C27H42O7

> <MOLECULAR_WEIGHT>
478.626

> <EXACT_MASS>
478.293053692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.76567949041443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{2-[(1R,2S,4aR,4bS,8aS,10aR)-2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl]-1-hydroxyethyl}-5-oxo-2,5-dihydrofuran-2-yl acetate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.2277340466666655

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.657948222609143

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9014917191409206

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0640935269956096

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
126.32099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{2-[(1R,2S,4aR,4bS,8aS,10aR)-2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-decahydrophenanthren-1-yl]-1-hydroxyethyl}-5-oxo-2H-furan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       8.171   2.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.456   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       5.954   3.437   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.833   0.307   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.386   1.760   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.516   2.104   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.048   4.932   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.078   3.788   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.585   4.108   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.615   2.963   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.061   5.572   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -4.368   6.438   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.890   6.178   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.034   7.208   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.873   8.740   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   15                                             
CONECT    8    7                                                            
CONECT    9    7    2   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22   23                                             
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   19   13   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   35                                                       
CONECT   34   27   35                                                       
CONECT   35   34   33   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₇

Average Mass

478.6260 Da

Monoisotopic Mass

478.29305 Da

IUPAC Name

3-{2-[(1R,2S,4aR,4bS,8aS,10aR)-2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl]-1-hydroxyethyl}-5-oxo-2,5-dihydrofuran-2-yl acetate

Traditional Name

3-{2-[(1R,2S,4aR,4bS,8aS,10aR)-2-hydroxy-2-(hydroxymethyl)-4b,8,8,10a-tetramethyl-decahydrophenanthren-1-yl]-1-hydroxyethyl}-5-oxo-2H-furan-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@]3(C)[C@@H](CC(O)C4=CC(=O)OC4OC(C)=O)[C@](O)(CO)CC[C@]3([H])[C@@]1(C)CCCC2(C)C

InChI Identifier

InChI=1S/C27H42O7/c1-16(29)33-23-17(13-22(31)34-23)18(30)14-21-26(5)11-7-19-24(2,3)9-6-10-25(19,4)20(26)8-12-27(21,32)15-28/h13,18-21,23,28,30,32H,6-12,14-15H2,1-5H3/t18?,19-,20+,21+,23?,25-,26+,27+/m0/s1

InChI Key

QNZZHRCSGTYEAW-REXWJDRESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cydonia oblonga	LOTUS Database	35616633
Cydonia vulgaris	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Cheilanthane sesterterpenoids

Alternative Parents

Substituents

Cheilanthane sesterterpenoid
18-hydroxysteroid
13-hydroxysteroid
Hydroxysteroid
17-hydroxysteroid
16-hydroxysteroid
Steroid
Hydrophenanthrene
Phenanthrene
Acylal
2-furanone
Dicarboxylic acid or derivatives
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Primary 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	2.78	ALOGPS
logP	3.23	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	1.9	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.32 m³·mol⁻¹	ChemAxon
Polarizability	52.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054369

Chemspider ID

8680247

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10504846

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 25-Acetylvulgaroside (NP0084781)

MOL for NP0084781 (25-Acetylvulgaroside)

3D MOL for NP0084781 (25-Acetylvulgaroside)

3D SDF for NP0084781 (25-Acetylvulgaroside)

3D-SDF for NP0084781 (25-Acetylvulgaroside)

PDB for NP0084781 (25-Acetylvulgaroside)

3D PDB for NP0084781 (25-Acetylvulgaroside)

SMILES for NP0084781 (25-Acetylvulgaroside)

INCHI for NP0084781 (25-Acetylvulgaroside)

Structure for NP0084781 (25-Acetylvulgaroside)

3D Structure for NP0084781 (25-Acetylvulgaroside)