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Showing NP-Card for Sinensiaxanthin (NP0046597)

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Record Information
Version2.0
Created at2022-03-17 20:08:30 UTC
Updated at2022-03-17 20:08:30 UTC
NP-MRD IDNP0046597
Secondary Accession NumbersNone
Natural Product Identification
Common NameSinensiaxanthin
DescriptionSinensiaxanthin belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Sinensiaxanthin is found in Malus domestica . Sinensiaxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046597 (Sinensiaxanthin)


  Mrv0541 02241221582D          

 30 31  0  0  0  0            999 V2000
   -5.0973    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8118    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8118    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0973    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3829    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3829    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4763    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5098    3.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848    3.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5263    1.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    2.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1908    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1908    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0487    2.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  6 22  1  0  0  0  0
  9 23  1  0  0  0  0
 13 24  1  0  0  0  0
 17 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
Download

3D MOL for NP0046597 (Sinensiaxanthin)

Download
3D SDF for NP0046597 (Sinensiaxanthin)

  Mrv0541 02241221582D          

 30 31  0  0  0  0            999 V2000
   -5.0973    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8118    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8118    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0973    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3829    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3829    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4763    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5098    3.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848    3.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5263    1.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    2.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1908    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9053    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1908    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0487    2.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  6 22  1  0  0  0  0
  9 23  1  0  0  0  0
 13 24  1  0  0  0  0
 17 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\CO)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O3/c1-21(11-7-8-12-22(2)15-10-18-28)13-9-14-23(3)16-17-27-25(4,5)19-24(29)20-26(27,6)30-27/h7-17,24,28-29H,18-20H2,1-6H3/b8-7+,13-9+,15-10+,17-16+,21-11+,22-12+,23-14+

> <INCHI_KEY>
GMQZSQMIENYQEB-JNOJMRGUSA-N

> <FORMULA>
C27H38O3

> <MOLECULAR_WEIGHT>
410.5888

> <EXACT_MASS>
410.282095082

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
50.90508072132656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(1E,3E,5E,7E,9E,11E,13E)-15-hydroxy-3,7,12-trimethylpentadeca-1,3,5,7,9,11,13-heptaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

> <ALOGPS_LOGP>
6.29

> <JCHEM_LOGP>
4.58579147

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.15619206159029

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.095722626759521

> <JCHEM_PKA_STRONGEST_BASIC>
-2.312310311833812

> <JCHEM_POLAR_SURFACE_AREA>
52.989999999999995

> <JCHEM_REFRACTIVITY>
133.51880000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E,3E,5E,7E,9E,11E,13E)-15-hydroxy-3,7,12-trimethylpentadeca-1,3,5,7,9,11,13-heptaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0046597 (Sinensiaxanthin)
Download
PDB for NP0046597 (Sinensiaxanthin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -9.515   6.050   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.849   5.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.849   3.740   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.515   2.970   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.181   3.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.181   5.280   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.848   6.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.514   5.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.180   6.050   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.847   5.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.513   6.050   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.179   5.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.154   6.050   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.488   5.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.822   6.050   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.156   5.280   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.489   6.050   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.285   7.384   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.745   7.384   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -12.182   2.970   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.848   2.970   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.848   4.510   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.180   7.590   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.154   7.590   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.823   5.280   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.157   6.050   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.490   5.280   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.824   6.050   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.823   3.740   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.158   5.280   0.000  0.00  0.00           O+0
CONECT    1    2    6   18   19                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21   22                                             
CONECT    6    1    5    7   22                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   25                                                       
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    3                                                            
CONECT   21    5                                                            
CONECT   22    5    6                                                       
CONECT   23    9                                                            
CONECT   24   13                                                            
CONECT   25   17   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   30                                                       
CONECT   29   25                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

Download
3D PDB for NP0046597 (Sinensiaxanthin)
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SMILES for NP0046597 (Sinensiaxanthin)
C\C(\C=C\CO)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C
Download
INCHI for NP0046597 (Sinensiaxanthin)
InChI=1S/C27H38O3/c1-21(11-7-8-12-22(2)15-10-18-28)13-9-14-23(3)16-17-27-25(4,5)19-24(29)20-26(27,6)30-27/h7-17,24,28-29H,18-20H2,1-6H3/b8-7+,13-9+,15-10+,17-16+,21-11+,22-12+,23-14+
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View in JSmol
SynonymsNot Available
Chemical FormulaC27H38O3
Average Mass410.5888 Da
Monoisotopic Mass410.28210 Da
IUPAC Name6-[(1E,3E,5E,7E,9E,11E,13E)-15-hydroxy-3,7,12-trimethylpentadeca-1,3,5,7,9,11,13-heptaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
Traditional Name6-[(1E,3E,5E,7E,9E,11E,13E)-15-hydroxy-3,7,12-trimethylpentadeca-1,3,5,7,9,11,13-heptaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
CAS Registry Number7235-40-7
SMILES
C\C(\C=C\CO)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C
InChI Identifier
InChI=1S/C27H38O3/c1-21(11-7-8-12-22(2)15-10-18-28)13-9-14-23(3)16-17-27-25(4,5)19-24(29)20-26(27,6)30-27/h7-17,24,28-29H,18-20H2,1-6H3/b8-7+,13-9+,15-10+,17-16+,21-11+,22-12+,23-14+
InChI KeyGMQZSQMIENYQEB-JNOJMRGUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Malus domesticaPlant
Malus pumilaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesterterpenoids  
Direct ParentSesterterpenoids  
Alternative Parents
Substituents
  • Sesterterpenoid
    • 

  • Long chain fatty alcohol
    • 

  • Fatty alcohol
    • 

  • Oxepane
    • 

  • Fatty acyl
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Dialkyl ether
    • 

  • Oxirane
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Primary alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.29ALOGPS
logP4.59ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)15.1ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.99 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity133.52 m³·mol⁻¹ChemAxon
Polarizability50.91 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005146  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13964732  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available