NP-MRD: Showing NP-Card for 9-Oxo-5-acetoxynerolidol (NP0058071)

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Record Information

Version

2.0

Created at

2022-04-28 03:27:50 UTC

Updated at

2022-04-28 03:27:50 UTC

NP-MRD ID

NP0058071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Oxo-5-acetoxynerolidol

Description

(3S,5R,6E)-3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,6,10-trien-5-yl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 9-Oxo-5-acetoxynerolidol is found in Anthemis austriaca. Based on a literature review very few articles have been published on (3S,5R,6E)-3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,6,10-trien-5-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282205272D          

 21 20  0  0  1  0            999 V2000
   -4.1763   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1914    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  6  0  0  0
 11 15  1  1  0  0  0
  9 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  7 20  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058071

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O4/c1-7-17(6,20)11-16(21-14(5)18)10-13(4)9-15(19)8-12(2)3/h7-8,10,16,20H,1,9,11H2,2-6H3/b13-10+/t16-,17+/m0/s1

> <INCHI_KEY>
AXXJTACQKRRZET-GABYWQGASA-N

> <FORMULA>
C17H26O4

> <MOLECULAR_WEIGHT>
294.391

> <EXACT_MASS>
294.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
32.69889216914552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,5R,6E)-3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,6,10-trien-5-yl acetate

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.6252544860000007

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.564893082287316

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.607039862050666

> <JCHEM_PKA_STRONGEST_BASIC>
-2.968543532090142

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
85.2507

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,5R,6E)-3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,6,10-trien-5-yl 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      -7.796  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.462  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.128  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.795   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.461  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.206   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.357   4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.127   5.747   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.897   1.746   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.461   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.207  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.462   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14   15                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15   11                                                            
CONECT   16    9   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    7                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(3S,5R,6E)-3-Hydroxy-3,7,11-trimethyl-9-oxododeca-1,6,10-trien-5-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₆O₄

Average Mass

294.3910 Da

Monoisotopic Mass

294.18311 Da

IUPAC Name

(3S,5R,6E)-3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,6,10-trien-5-yl acetate

Traditional Name

(3S,5R,6E)-3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,6,10-trien-5-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H26O4/c1-7-17(6,20)11-16(21-14(5)18)10-13(4)9-15(19)8-12(2)3/h7-8,10,16,20H,1,9,11H2,2-6H3/b13-10+/t16-,17+/m0/s1

InChI Key

AXXJTACQKRRZET-GABYWQGASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthemis austriaca	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty alcohol ester
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Acryloyl-group
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.72	ALOGPS
logP	2.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.61	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	85.25 m³·mol⁻¹	ChemAxon
Polarizability	32.7 Å³	ChemAxon
Number of Rings	0	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

162848526

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 9-Oxo-5-acetoxynerolidol (NP0058071)

MOL for NP0058071 (9-Oxo-5-acetoxynerolidol)

3D MOL for NP0058071 (9-Oxo-5-acetoxynerolidol)

3D SDF for NP0058071 (9-Oxo-5-acetoxynerolidol)

3D-SDF for NP0058071 (9-Oxo-5-acetoxynerolidol)

PDB for NP0058071 (9-Oxo-5-acetoxynerolidol)

3D PDB for NP0058071 (9-Oxo-5-acetoxynerolidol)

SMILES for NP0058071 (9-Oxo-5-acetoxynerolidol)

INCHI for NP0058071 (9-Oxo-5-acetoxynerolidol)

Structure for NP0058071 (9-Oxo-5-acetoxynerolidol)

3D Structure for NP0058071 (9-Oxo-5-acetoxynerolidol)