NP-MRD: Showing NP-Card for 12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside (NP0062705)

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Record Information

Version

2.0

Created at

2022-04-28 07:17:15 UTC

Updated at

2022-04-28 07:17:15 UTC

NP-MRD ID

NP0062705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside

Description

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-{[(3R,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. 12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside is found in Gaillardia aestivalis. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-{[(3R,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209172D          

 34 34  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 30 32  1  0  0  0  0
  2 33  1  6  0  0  0
  1 34  1  1  0  0  0
M  END

     RDKit          3D

 74 74  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282209172D          

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  3 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  2 33  1  6  0  0  0
  1 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062705

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O9/c1-7-25(6,13-9-12-16(2)10-8-11-17(3)14-26)34-24-23(32-19(5)28)22(30)21(29)20(33-24)15-31-18(4)27/h7,11-12,20-24,26,29-30H,1,8-10,13-15H2,2-6H3/b16-12+,17-11+/t20-,21-,22+,23-,24+,25+/m1/s1

> <INCHI_KEY>
ZZRXUBHGMJNKEB-PSTDGFACSA-N

> <FORMULA>
C25H40O9

> <MOLECULAR_WEIGHT>
484.586

> <EXACT_MASS>
484.267232868

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.132219662624166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-{[(3R,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.137850745999998

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.129858281720711

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.7005150708886

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797068162575387

> <JCHEM_POLAR_SURFACE_AREA>
131.75000000000003

> <JCHEM_REFRACTIVITY>
126.50019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-{[(3R,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -13.090   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.897  -4.414   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -5.747   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.437  -1.746   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3   33                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14   26   28                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   17                                                            
CONECT   26   13   27                                                       
CONECT   27   26                                                            
CONECT   28   13                                                            
CONECT   29    3   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    2                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-5-(Acetyloxy)-3,4-dihydroxy-6-{[(3R,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₄₀O₉

Average Mass

484.5860 Da

Monoisotopic Mass

484.26723 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-{[(3R,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-3,4-dihydroxy-6-{[(3R,6E,10E)-12-hydroxy-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H40O9/c1-7-25(6,13-9-12-16(2)10-8-11-17(3)14-26)34-24-23(32-19(5)28)22(30)21(29)20(33-24)15-31-18(4)27/h7,11-12,20-24,26,29-30H,1,8-10,13-15H2,2-6H3/b16-12+,17-11+/t20-,21-,22+,23-,24+,25+/m1/s1

InChI Key

ZZRXUBHGMJNKEB-PSTDGFACSA-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
Gaillardia aestivalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Sesquiterpenoid
Farsesane sesquiterpenoid
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.3	ALOGPS
logP	2.14	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.75 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	126.5 m³·mol⁻¹	ChemAxon
Polarizability	53.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

162939380

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside (NP0062705)

MOL for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

3D MOL for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

3D SDF for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

3D-SDF for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

PDB for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

3D PDB for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

SMILES for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

INCHI for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

Structure for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)

3D Structure for NP0062705 (12-Hydroxynerolidol 3-O-beta-D-2'-acetylglucoside)