NP-MRD: Showing NP-Card for Apo-9-zeaxanthinone (NP0045777)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:37:14 UTC

Updated at

2022-03-17 19:37:14 UTC

NP-MRD ID

NP0045777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apo-9-zeaxanthinone

Description

Apo-9-zeaxanthinone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Apo-9-zeaxanthinone is found in Chenopodium album , Phaseolus vulgaris , Senecio vulgaris and Viburnum dilatatum. Apo-9-zeaxanthinone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307072017432D          

 15 15  0  0  0  0            999 V2000
   -1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455    1.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2 10  1  1  0  0  0
  4 11  1  0  0  0  0
  8 12  2  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1

> <INCHI_KEY>
HFRZSVYKDDZRQY-MVIFTORASA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.048416947252342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.8889051433333337

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.705448550238387

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.907213401199783

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0896768165158917

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
63.49159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-hydroxy-β-ionone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-20         0                                  
HETATM    1  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.668   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.668  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.667  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.964   1.971   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.018   1.953   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8                                                            
CONECT   10    2                                                            
CONECT   11    4                                                            
CONECT   12    8                                                            
CONECT   13   15                                                            
CONECT   14   15                                                            
CONECT   15   13   14    5    1                                             
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(3E)-4-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one	HMDB
(3E)-4-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-3-buten-2-one	HMDB
(3R)-3-Hydroxy-beta-ionone	HMDB
(3R)-3-Hydroxy-β-ionone	HMDB
(R)-(-)-3-Hydroxy-beta-ionone	HMDB
(R)-(-)-3-Hydroxy-β-ionone	HMDB
(R)-3-Hydroxy-beta-ionone	HMDB
(R)-3-Hydroxy-β-ionone	HMDB
3-Hydroxy-beta-ionone	HMDB
3-Hydroxy-β-ionone	HMDB
3beta-Hydroxymegastigma-5,7-dien-9-one	HMDB
3β-Hydroxymegastigma-5,7-dien-9-one	HMDB
Apo-9-zeaxanthinone	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Mass

208.2967 Da

Monoisotopic Mass

208.14633 Da

IUPAC Name

(3E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one

Traditional Name

(3R)-hydroxy-β-ionone

CAS Registry Number

50281-38-4

SMILES

CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1

InChI Key

HFRZSVYKDDZRQY-MVIFTORASA-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
Capsicum annuum	FooDB	KNAPSACK
Chenopodium album	Plant	KNApSAcK
Phaseolus vulgaris	Plant	KNApSAcK
Senecio vulgaris	LOTUS Database	35616633
Viburnum dilatatum	LOTUS Database	35616633

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

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

apo carotenoid monoterpenoid (CHEBI:53173 )

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	2.1	ALOGPS
logP	1.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.49 m³·mol⁻¹	ChemAxon
Polarizability	24.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon