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Showing NP-Card for Honyucitrin (NP0047665)

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Record Information
Version2.0
Created at2022-03-17 20:43:55 UTC
Updated at2022-03-17 20:43:55 UTC
NP-MRD IDNP0047665
Secondary Accession NumbersNone
Natural Product Identification
Common NameHonyucitrin
DescriptionHonyucitrin belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position. Thus, honyucitrin is considered to be a flavonoid lipid molecule. Honyucitrin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Honyucitrin has been detected, but not quantified in, citrus and pummelo. This could make honyucitrin a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047665 (Honyucitrin)


  Mrv0541 05061307102D          

 30 32  0  0  0  0            999 V2000
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 17 10  2  0  0  0  0
 18  9  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20 11  1  0  0  0  0
 21 13  1  0  0  0  0
 22 13  2  0  0  0  0
 22 18  1  0  0  0  0
 23 12  2  0  0  0  0
 24 20  2  0  0  0  0
 24 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 16  2  0  0  0  0
 25 17  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 21  2  0  0  0  0
 29 25  1  0  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
M  END
Download

3D MOL for NP0047665 (Honyucitrin)

Download
3D SDF for NP0047665 (Honyucitrin)

  Mrv0541 05061307102D          

 30 32  0  0  0  0            999 V2000
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 17 10  2  0  0  0  0
 18  9  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20 11  1  0  0  0  0
 21 13  1  0  0  0  0
 22 13  2  0  0  0  0
 22 18  1  0  0  0  0
 23 12  2  0  0  0  0
 24 20  2  0  0  0  0
 24 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 16  2  0  0  0  0
 25 17  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 21  2  0  0  0  0
 29 25  1  0  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O5/c1-14(2)5-7-16-9-18(10-17(25(16)29)8-6-15(3)4)22-13-21(28)24-20(27)11-19(26)12-23(24)30-22/h5-6,9-13,26-27,29H,7-8H2,1-4H3

> <INCHI_KEY>
DOFKPAVSYGZVQD-UHFFFAOYSA-N

> <FORMULA>
C25H26O5

> <MOLECULAR_WEIGHT>
406.4709

> <EXACT_MASS>
406.178023942

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.991580294832104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
6.163823132333334

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.297097477117953

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.629138034900379

> <JCHEM_PKA_STRONGEST_BASIC>
-5.174527193655405

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
121.39949999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
honyucitrin

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047665 (Honyucitrin)
Download
PDB for NP0047665 (Honyucitrin)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    7   14                                                       
CONECT    6    8   15                                                       
CONECT    7    5   16                                                       
CONECT    8    6   17                                                       
CONECT    9   16   18                                                       
CONECT   10   17   18                                                       
CONECT   11   19   20                                                       
CONECT   12   19   23                                                       
CONECT   13   21   22                                                       
CONECT   14    1    2    5                                                  
CONECT   15    3    4    6                                                  
CONECT   16    7    9   25                                                  
CONECT   17    8   10   25                                                  
CONECT   18    9   10   22                                                  
CONECT   19   11   12   26                                                  
CONECT   20   11   24   27                                                  
CONECT   21   13   24   28                                                  
CONECT   22   13   18   30                                                  
CONECT   23   12   24   30                                                  
CONECT   24   20   21   23                                                  
CONECT   25   16   17   29                                                  
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   21                                                            
CONECT   29   25                                                            
CONECT   30   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Download
3D PDB for NP0047665 (Honyucitrin)
Download
SMILES for NP0047665 (Honyucitrin)
CC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
Download
INCHI for NP0047665 (Honyucitrin)
InChI=1S/C25H26O5/c1-14(2)5-7-16-9-18(10-17(25(16)29)8-6-15(3)4)22-13-21(28)24-20(27)11-19(26)12-23(24)30-22/h5-6,9-13,26-27,29H,7-8H2,1-4H3
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View in JSmol
Synonyms
ValueSource
5,7-Dihydroxy-2-[4-hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one, 9ciHMDB
Chemical FormulaC25H26O5
Average Mass406.4709 Da
Monoisotopic Mass406.17802 Da
IUPAC Name5,7-dihydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one
Traditional Namehonyucitrin
CAS Registry Number114542-44-8
SMILES
CC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C25H26O5/c1-14(2)5-7-16-9-18(10-17(25(16)29)8-6-15(3)4)22-13-21(28)24-20(27)11-19(26)12-23(24)30-22/h5-6,9-13,26-27,29H,7-8H2,1-4H3
InChI KeyDOFKPAVSYGZVQD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus maximaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavones  
Direct Parent3'-prenylated flavones  
Alternative Parents
Substituents
  • 3'-prenylated flavone
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Phenol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP5.15ALOGPS
logP6.16ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)6.63ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.4 m³·mol⁻¹ChemAxon
Polarizability45.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033536  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011596  
KNApSAcK IDC00004019  
Chemspider ID24843463  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257865  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available