NP-MRD: Showing NP-Card for 9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate (NP0064155)

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Record Information

Version

1.0

Created at

2022-04-28 08:25:53 UTC

Updated at

2022-04-28 08:25:54 UTC

NP-MRD ID

NP0064155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate

Description

[(2S,3S,4S,5R,6R)-5-(acetyloxy)-3,4-dihydroxy-6-{[(4R,6E,10R)-10-hydroxy-2,6,10-trimethyldodeca-2,6,11-trien-4-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate is found in Geigeria ornativa. Based on a literature review very few articles have been published on [(2S,3S,4S,5R,6R)-5-(acetyloxy)-3,4-dihydroxy-6-{[(4R,6E,10R)-10-hydroxy-2,6,10-trimethyldodeca-2,6,11-trien-4-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210252D          

 34 34  0  0  1  0            999 V2000
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  2 33  1  6  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282210252D          

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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>
NP0064155

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O9/c1-8-25(7,30)11-9-10-16(4)13-19(12-15(2)3)33-24-23(32-18(6)27)22(29)21(28)20(34-24)14-31-17(5)26/h8,10,12,19-24,28-30H,1,9,11,13-14H2,2-7H3/b16-10+/t19-,20-,21+,22-,23+,24+,25-/m0/s1

> <INCHI_KEY>
AJDDTHHUOKHMSJ-KTZDBKJGSA-N

> <FORMULA>
C25H40O9

> <MOLECULAR_WEIGHT>
484.586

> <EXACT_MASS>
484.267232868

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.426785656118234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.1878108356666646

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.131149237435128

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.700575977288509

> <JCHEM_PKA_STRONGEST_BASIC>
-1.284980657364133

> <JCHEM_POLAR_SURFACE_AREA>
131.75000000000003

> <JCHEM_REFRACTIVITY>
126.24099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4S,5R,6R)-5-(acetyloxy)-3,4-dihydroxy-6-{[(4R,6E,10R)-10-hydroxy-2,6,10-trimethyldodeca-2,6,11-trien-4-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      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   6.160   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  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.437  -6.366   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.897  -9.034   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -6.930   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   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26   27                                             
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   23                                                            
CONECT   28   19                                                            
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
[(2S,3S,4S,5R,6R)-5-(Acetyloxy)-3,4-dihydroxy-6-{[(4R,6E,10R)-10-hydroxy-2,6,10-trimethyldodeca-2,6,11-trien-4-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₄₀O₉

Average Mass

484.5860 Da

Monoisotopic Mass

484.26723 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H40O9/c1-8-25(7,30)11-9-10-16(4)13-19(12-15(2)3)33-24-23(32-18(6)27)22(29)21(28)20(34-24)14-31-17(5)26/h8,10,12,19-24,28-30H,1,9,11,13-14H2,2-7H3/b16-10+/t19-,20-,21+,22-,23+,24+,25-/m0/s1

InChI Key

AJDDTHHUOKHMSJ-KTZDBKJGSA-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
Geigeria ornativa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Fatty acyl
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.91	ALOGPS
logP	2.19	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-1.3	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	14	ChemAxon
Refractivity	126.24 m³·mol⁻¹	ChemAxon
Polarizability	51.43 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

163045853

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate (NP0064155)

MOL for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

3D MOL for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

3D SDF for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

3D-SDF for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

PDB for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

3D PDB for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

SMILES for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

INCHI for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

Structure for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)

3D Structure for NP0064155 (9-Hydroxynerolidol-9-O-beta-D-glucopyranoside-2',6'-O-diacetate)