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Showing NP-Card for Artocarpetin B (NP0047560)

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Record Information
Version2.0
Created at2022-03-17 20:42:10 UTC
Updated at2022-03-17 20:42:10 UTC
NP-MRD IDNP0047560
Secondary Accession NumbersNone
Natural Product Identification
Common NameArtocarpetin B
DescriptionArtocarpetin B belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. Thus, artocarpetin b is considered to be a flavonoid lipid molecule. Artocarpetin B is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Artocarpetin B has been detected, but not quantified in, fruits and jackfruits. Artocarpetin B is found in Artocarpus integer. This could make artocarpetin b a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047560 (Artocarpetin B)


  Mrv0541 05061306572D          

 28 30  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    2.1434   -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
    5.7158   -1.6500    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    5.0013   -0.4125    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
    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
    5.0013   -1.2375    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
    4.2868    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
    2.8579    0.0000    0.0000 C   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
    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
    4.2868   -1.6500    0.0000 O   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
    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  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 14  2  0  0  0  0
 19 10  1  0  0  0  0
 19 15  2  0  0  0  0
 20 11  2  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 15  1  0  0  0  0
 22 21  2  0  0  0  0
 23 13  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26  3  1  0  0  0  0
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 27  4  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
M  END
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3D MOL for NP0047560 (Artocarpetin B)

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3D SDF for NP0047560 (Artocarpetin B)

  Mrv0541 05061306572D          

 28 30  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    2.1434   -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
    5.7158   -1.6500    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    5.0013   -0.4125    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
    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
    5.0013   -1.2375    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
    4.2868    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
    2.8579    0.0000    0.0000 C   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
    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
    4.2868   -1.6500    0.0000 O   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
    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  2  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 14  2  0  0  0  0
 19 10  1  0  0  0  0
 19 15  2  0  0  0  0
 20 11  2  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 15  1  0  0  0  0
 22 21  2  0  0  0  0
 23 13  1  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26  3  1  0  0  0  0
 26 18  1  0  0  0  0
 27  4  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=C(OC)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O6/c1-12(2)5-7-15-19(27-4)10-16(24)21-17(25)11-20(28-22(15)21)14-8-6-13(23)9-18(14)26-3/h5-6,8-11,23-24H,7H2,1-4H3

> <INCHI_KEY>
AGQBGLZQKDLJAR-UHFFFAOYSA-N

> <FORMULA>
C22H22O6

> <MOLECULAR_WEIGHT>
382.4065

> <EXACT_MASS>
382.141638436

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
40.46503980676159

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
4.423478923333334

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.98252391267116

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.342988964773024

> <JCHEM_PKA_STRONGEST_BASIC>
-4.510938924455925

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
108.10219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artocarpetin B

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047560 (Artocarpetin B)
Download
PDB for NP0047560 (Artocarpetin B)
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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   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       9.336  -2.310   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5    7   12                                                       
CONECT    6    8   13                                                       
CONECT    7    5   15                                                       
CONECT    8    6   14                                                       
CONECT    9   13   18                                                       
CONECT   10   16   19                                                       
CONECT   11   17   20                                                       
CONECT   12    1    2    5                                                  
CONECT   13    6    9   23                                                  
CONECT   14    8   18   20                                                  
CONECT   15    7   19   22                                                  
CONECT   16   10   21   24                                                  
CONECT   17   11   21   25                                                  
CONECT   18    9   14   26                                                  
CONECT   19   10   15   27                                                  
CONECT   20   11   14   28                                                  
CONECT   21   16   17   22                                                  
CONECT   22   15   21   28                                                  
CONECT   23   13                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26    3   18                                                       
CONECT   27    4   19                                                       
CONECT   28   20   22                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

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3D PDB for NP0047560 (Artocarpetin B)
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SMILES for NP0047560 (Artocarpetin B)
COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=C(OC)C=C(O)C=C1
Download
INCHI for NP0047560 (Artocarpetin B)
InChI=1S/C22H22O6/c1-12(2)5-7-15-19(27-4)10-16(24)21-17(25)11-20(28-22(15)21)14-8-6-13(23)9-18(14)26-3/h5-6,8-11,23-24H,7H2,1-4H3
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View in JSmol
Synonyms
ValueSource
4',5-Dihydroxy-2',7-dimethoxy-8-prenylflavoneHMDB
5-Hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-oneHMDB
Chemical FormulaC22H22O6
Average Mass382.4065 Da
Monoisotopic Mass382.14164 Da
IUPAC Name5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Nameartocarpetin B
CAS Registry Number170894-22-1
SMILES
COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=C(OC)C=C(O)C=C1
InChI Identifier
InChI=1S/C22H22O6/c1-12(2)5-7-15-19(27-4)10-16(24)21-17(25)11-20(28-22(15)21)14-8-6-13(23)9-18(14)26-3/h5-6,8-11,23-24H,7H2,1-4H3
InChI KeyAGQBGLZQKDLJAR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artocarpus champedenLOTUS Database
Artocarpus heterophyllusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavones  
Direct Parent8-prenylated flavones  
Alternative Parents
Substituents
  • 8-prenylated flavone
    • 

  • 7-methoxyflavonoid-skeleton
    • 

  • 2p-methoxyflavonoid-skeleton
    • 

  • Hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Methoxyphenol
    • 

  • Methoxybenzene
    • 

  • Anisole
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen 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
logP3.86ALOGPS
logP4.42ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.34ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.1 m³·mol⁻¹ChemAxon
Polarizability40.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033148  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011152  
KNApSAcK IDC00013418  
Chemspider ID24843906  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15231525  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available