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Showing NP-Card for Artonin L (NP0049694)

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Record Information
Version2.0
Created at2022-03-17 21:16:35 UTC
Updated at2022-03-17 21:16:35 UTC
NP-MRD IDNP0049694
Secondary Accession NumbersNone
Natural Product Identification
Common NameArtonin L
DescriptionArtonin L belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Thus, artonin L is considered to be a flavonoid lipid molecule. Artonin L is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Artonin L has been detected, but not quantified in, fruits and jackfruits. Artonin L is found in Artocarpus chama and Artocarpus integer. This could make artonin L a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049694 (Artonin L)


  Mrv0541 02241210182D          

 29 33  0  0  0  0            999 V2000
    2.1007   -1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118    0.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1846   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1846    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8978   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726   -1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5286   -1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978    0.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978    1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 23  2  0  0  0  0
  2  3  2  0  0  0  0
  2 25  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  1  0  0  0  0
  4 26  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 29  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
Download

3D MOL for NP0049694 (Artonin L)

Download
3D SDF for NP0049694 (Artonin L)

  Mrv0541 02241210182D          

 29 33  0  0  0  0            999 V2000
    2.1007   -1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118    0.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1846   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1846    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8978   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -0.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007    0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -0.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6726   -1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5286   -1.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978    0.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978    1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    1.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 23  2  0  0  0  0
  2  3  2  0  0  0  0
  2 25  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  1  0  0  0  0
  4 26  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 26  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 29  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C3C(C1)C(C)(C)OC3=C(O)C=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O7/c1-22(2)11-7-10-19(25)17-12(23)5-9(26-3)6-15(17)28-20(10)18-14(27-4)8-13(24)21(29-22)16(11)18/h5-6,8,11,23-24H,7H2,1-4H3

> <INCHI_KEY>
LDQNIBPJKBVZEF-UHFFFAOYSA-N

> <FORMULA>
C22H20O7

> <MOLECULAR_WEIGHT>
396.39

> <EXACT_MASS>
396.120902994

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
41.126173503702674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,17-dihydroxy-6,19-dimethoxy-14,14-dimethyl-3,15-dioxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-1(20),2(11),4(9),5,7,16,18-heptaen-10-one

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.1265096056666675

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.574023230525423

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.260304468573883

> <JCHEM_PKA_STRONGEST_BASIC>
-4.364576363009617

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
105.1147

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artonin L

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049694 (Artonin L)
Download
PDB for NP0049694 (Artonin L)
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       3.921  -3.463   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.255  -2.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.255  -1.154   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.369   0.280   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.078   3.463   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.078   1.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.412   1.154   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.412  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.744  -1.154   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.078  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.078   1.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.744   1.924   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.744   3.463   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.743  -0.385   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.409  -1.154   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.078  -1.154   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.256  -0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.256   1.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.587   1.924   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.921   1.154   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.921  -0.385   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.587  -1.154   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.587  -2.694   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.256  -3.463   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.587  -3.463   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.409   1.552   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.409   3.091   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.743   2.322   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.078  -2.694   0.000  0.00  0.00           C+0
CONECT    1    2   23                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3   26                                                       
CONECT    5    6                                                            
CONECT    6    5    7   18                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12    7   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   10   14                                                       
CONECT   16    8   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18    6   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21    3   20   22                                                  
CONECT   22   17   21   23                                                  
CONECT   23    1   22   24                                                  
CONECT   24   23   29                                                       
CONECT   25    2                                                            
CONECT   26    4   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

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3D PDB for NP0049694 (Artonin L)
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SMILES for NP0049694 (Artonin L)
COC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C3C(C1)C(C)(C)OC3=C(O)C=C2OC
Download
INCHI for NP0049694 (Artonin L)
InChI=1S/C22H20O7/c1-22(2)11-7-10-19(25)17-12(23)5-9(26-3)6-15(17)28-20(10)18-14(27-4)8-13(24)21(29-22)16(11)18/h5-6,8,11,23-24H,7H2,1-4H3
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View in JSmol
Synonyms
ValueSource
5a,6-Dihydro-3,8-dihydroxy-1,10-dimethoxy-5,5-dimethyl-5H,7H-benzofuro[3,4-BC]xanthen-7-oneHMDB
Chemical FormulaC22H20O7
Average Mass396.3900 Da
Monoisotopic Mass396.12090 Da
IUPAC Name8,17-dihydroxy-6,19-dimethoxy-14,14-dimethyl-3,15-dioxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-1(20),2(11),4(9),5,7,16,18-heptaen-10-one
Traditional Nameartonin L
CAS Registry Number148719-52-2
SMILES
COC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C3C(C1)C(C)(C)OC3=C(O)C=C2OC
InChI Identifier
InChI=1S/C22H20O7/c1-22(2)11-7-10-19(25)17-12(23)5-9(26-3)6-15(17)28-20(10)18-14(27-4)8-13(24)21(29-22)16(11)18/h5-6,8,11,23-24H,7H2,1-4H3
InChI KeyLDQNIBPJKBVZEF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artocarpus chamaLOTUS Database
Artocarpus champedenLOTUS Database
Artocarpus heterophyllusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct ParentXanthones  
Alternative Parents
Substituents
  • Naphthopyranone
    • 

  • Xanthone
    • 

  • Naphthopyran
    • 

  • Chromone
    • 

  • Naphthalene
    • 

  • Coumaran
    • 

  • Anisole
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • 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
logP3.84ALOGPS
logP3.13ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)6.26ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity105.11 m³·mol⁻¹ChemAxon
Polarizability41.13 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040674  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020471  
KNApSAcK IDC00013479  
Chemspider ID24844321  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258662  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available