Np mrd loader

Showing NP-Card for Bullatacinone (NP0047875)

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Record Information
Version2.0
Created at2022-03-17 20:47:23 UTC
Updated at2022-03-17 20:47:24 UTC
NP-MRD IDNP0047875
Secondary Accession NumbersNone
Natural Product Identification
Common NameBullatacinone
Description2,4-Cis-Trilobacinone, also known as bullatacinone or 2,4-trans-asimicinone, belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 2,4-Cis-Trilobacinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,4-cis-Trilobacinone has been detected, but not quantified in, fruits. Bullatacinone is found in Annona bullata, Annona cherimola, Annona squamosa , Asimina triloba , Annona rensoniana and Rollinia papilionella. This could make 2,4-cis-trilobacinone a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047875 (Bullatacinone)


  Mrv0541 02241210572D          

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M  END
Download

3D MOL for NP0047875 (Bullatacinone)

Download
3D SDF for NP0047875 (Bullatacinone)

  Mrv0541 02241210572D          

 44 46  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0047875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1CC(CC(C)=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3

> <INCHI_KEY>
KGGVWMAPBXIMEM-UHFFFAOYSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.9157

> <EXACT_MASS>
622.480854466

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
78.08872223843731

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(11-hydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-3-(2-oxopropyl)oxolan-2-one

> <ALOGPS_LOGP>
7.35

> <JCHEM_LOGP>
8.472050788999999

> <ALOGPS_LOGS>
-6.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.500804158429037

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.898978347148773

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148665094183956

> <JCHEM_POLAR_SURFACE_AREA>
102.28999999999999

> <JCHEM_REFRACTIVITY>
174.5437

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.13e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(11-hydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-3-(2-oxopropyl)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047875 (Bullatacinone)
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PDB for NP0047875 (Bullatacinone)
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      -9.539  -1.862   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.539  -3.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.783  -4.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.305  -5.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.765  -5.780   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.289  -4.315   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -8.289  -0.957   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.765   0.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.313   0.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.796  -0.957   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.858   1.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.858  -7.027   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.485  -8.436   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -8.485   3.166   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.523   2.526   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.189   1.757   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.855   2.526   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.521   1.757   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.186   2.526   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.148   1.757   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.482   2.526   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.816   1.757   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.151   2.526   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.485   1.757   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.819   2.526   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.523  -6.259   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.189  -7.027   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.855  -6.259   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.521  -7.027   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.186  -6.259   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.148  -7.027   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.482  -6.259   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.816  -7.027   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.151  -6.259   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.485  -7.027   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.225   1.888   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.264   3.030   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.495   4.372   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.979   4.055   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.796   2.863   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       9.128   5.778   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.225   7.030   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.858   8.436   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       6.691   6.876   0.000  0.00  0.00           O+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    2    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    1    9                                                       
CONECT   11    8   14   15                                                  
CONECT   12    5   13   26                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   36   39                                                  
CONECT   26   12   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   25   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39   41                                                  
CONECT   39   25   38                                                       
CONECT   40   37                                                            
CONECT   41   38   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

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3D PDB for NP0047875 (Bullatacinone)
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SMILES for NP0047875 (Bullatacinone)
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1CC(CC(C)=O)C(=O)O1
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INCHI for NP0047875 (Bullatacinone)
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3
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View in JSmol
Synonyms
ValueSource
2,4-cis-AsimicinoneHMDB
BullatacinoneHMDB
2,4-trans-AsimicinoneHMDB
AsimicinoneHMDB
RollinoneMeSH
Chemical FormulaC37H66O7
Average Mass622.9157 Da
Monoisotopic Mass622.48085 Da
IUPAC Name5-(11-hydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-3-(2-oxopropyl)oxolan-2-one
Traditional Name5-(11-hydroxy-11-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}undecyl)-3-(2-oxopropyl)oxolan-2-one
CAS Registry Number189686-30-4
SMILES
CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCC1CC(CC(C)=O)C(=O)O1
InChI Identifier
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3
InChI KeyKGGVWMAPBXIMEM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona bullataPlant
Annona cherimolaLOTUS Database
Annona reticulataFooDB
Annona squamosaPlant
Asimina trilobaPlant
Rollinia membranaceaLOTUS Database
Rollinia papilionellaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohols  
Direct ParentAnnonaceous acetogenins  
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
    • 

  • Long chain fatty alcohol
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP7.35ALOGPS
logP8.47ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity174.54 m³·mol⁻¹ChemAxon
Polarizability78.09 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0032097  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010607  
KNApSAcK IDC00001302  
Chemspider ID115303  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound130310  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References