Np mrd loader

Showing NP-Card for Glabranin (NP0047368)

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Record Information
Version1.0
Created at2022-03-17 20:39:02 UTC
Updated at2022-03-17 20:39:02 UTC
NP-MRD IDNP0047368
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlabranin
DescriptionGlabranin 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. Glabranin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Glabranin has been detected, but not quantified in, a few different foods, such as alcoholic beverages, fruits, and sugar apples. Glabranin is found in Annona glabra , Annona glauca , Glycyrrhiza glabra , Glycyrrhiza lepidota , Glycyrrhiza uralensis, Helichrysum forskahlii , Piscidia erythrina, Piscidia piscipula and Sophora tomentosa. It was first documented in 2000 (PMID: 11413487). This could make glabranin a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047368 (Glabranin)


  Mrv0541 05061306222D          

 44 45  0  0  0  0            999 V2000
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   -3.5081    0.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1039   -3.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4395   -3.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9546   -2.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D MOL for NP0047368 (Glabranin)

Download
3D SDF for NP0047368 (Glabranin)

  Mrv0541 05061306222D          

 44 45  0  0  0  0            999 V2000
   12.7014   -9.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.7382   -5.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1039   -3.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4395   -3.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9546   -2.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8052   -1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0047368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC\C=C\CCC(O)C(O)CCC(O)C1CCC(CCCCCCCC(O)CC2=CC(C)OC2=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-33(39)34(40)24-25-35(41)36-26-23-32(44-36)21-18-15-13-14-17-20-31(38)28-30-27-29(2)43-37(30)42/h12,16,27,29,31-36,38-41H,3-11,13-15,17-26,28H2,1-2H3/b16-12+

> <INCHI_KEY>
OOKJEMBYFZCLNC-FOWTUZBSSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.9157

> <EXACT_MASS>
622.480854466

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
77.75522109246421

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-hydroxy-9-{5-[(8E)-1,4,5-trihydroxynonadec-8-en-1-yl]oxolan-2-yl}nonyl)-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
7.02

> <JCHEM_LOGP>
8.233470311333335

> <ALOGPS_LOGS>
-5.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.255390136847108

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.691066048666073

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022871174243

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
179.66179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.65e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxy-9-{5-[(8E)-1,4,5-trihydroxynonadec-8-en-1-yl]oxolan-2-yl}nonyl)-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047368 (Glabranin)
Download
PDB for NP0047368 (Glabranin)
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      23.709 -17.853   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.548   1.318   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.336 -16.446   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.430 -15.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.057 -13.794   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.152 -12.548   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.778 -11.141   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.873  -9.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.499  -8.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.594  -7.242   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.220  -5.835   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.315  -4.589   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.422   1.675   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.089   2.445   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.756   2.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.942  -3.182   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.755   1.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.090   1.675   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.036  -1.937   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.421   2.445   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.423   2.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.505  -2.098   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.918   0.144   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.163   0.233   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.631   0.072   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.425  -0.177   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.986   2.302   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.017   1.157   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.580   1.675   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.088   1.675   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.757   1.675   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.600  -0.852   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.068  -1.013   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.726   1.318   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.195   1.157   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.740   0.144   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.088   0.135   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      20.226   0.555   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      17.442  -2.420   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      15.352   2.725   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -1.596  -0.887   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -4.247  -0.177   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      12.164   2.302   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   29                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   16                                                       
CONECT   13   14   15                                                       
CONECT   14   13   17                                                       
CONECT   15   13   18                                                       
CONECT   16   12   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   31                                                       
CONECT   21   18   32                                                       
CONECT   22   19   33                                                       
CONECT   23   26   32                                                       
CONECT   24   25   34                                                       
CONECT   25   24   35                                                       
CONECT   26   23   36                                                       
CONECT   27   29   30                                                       
CONECT   28   30   31                                                       
CONECT   29    2   27   43                                                  
CONECT   30   27   28   37                                                  
CONECT   31   20   28   38                                                  
CONECT   32   21   23   44                                                  
CONECT   33   22   34   39                                                  
CONECT   34   24   33   40                                                  
CONECT   35   25   36   41                                                  
CONECT   36   26   35   44                                                  
CONECT   37   30   42   43                                                  
CONECT   38   31                                                            
CONECT   39   33                                                            
CONECT   40   34                                                            
CONECT   41   35                                                            
CONECT   42   37                                                            
CONECT   43   29   37                                                       
CONECT   44   32   36                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

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3D PDB for NP0047368 (Glabranin)
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SMILES for NP0047368 (Glabranin)
CCCCCCCCCC\C=C\CCC(O)C(O)CCC(O)C1CCC(CCCCCCCC(O)CC2=CC(C)OC2=O)O1
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INCHI for NP0047368 (Glabranin)
InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-33(39)34(40)24-25-35(41)36-26-23-32(44-36)21-18-15-13-14-17-20-31(38)28-30-27-29(2)43-37(30)42/h12,16,27,29,31-36,38-41H,3-11,13-15,17-26,28H2,1-2H3/b16-12+
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View in JSmol
Synonyms
ValueSource
(S)-5,7-Dihydroxy-8-(3-methylbut-2-ene)flavanoneHMDB
GlabranineHMDB
Chemical FormulaC37H66O7
Average Mass622.9157 Da
Monoisotopic Mass622.48085 Da
IUPAC Name3-(2-hydroxy-9-{5-[(8E)-1,4,5-trihydroxynonadec-8-en-1-yl]oxolan-2-yl}nonyl)-5-methyl-2,5-dihydrofuran-2-one
Traditional Name3-(2-hydroxy-9-{5-[(8E)-1,4,5-trihydroxynonadec-8-en-1-yl]oxolan-2-yl}nonyl)-5-methyl-5H-furan-2-one
CAS Registry Number41983-91-9
SMILES
CCCCCCCCCC\C=C\CCC(O)C(O)CCC(O)C1CCC(CCCCCCCC(O)CC2=CC(C)OC2=O)O1
InChI Identifier
InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-33(39)34(40)24-25-35(41)36-26-23-32(44-36)21-18-15-13-14-17-20-31(38)28-30-27-29(2)43-37(30)42/h12,16,27,29,31-36,38-41H,3-11,13-15,17-26,28H2,1-2H3/b16-12+
InChI KeyOOKJEMBYFZCLNC-FOWTUZBSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona glabraPlant
Annona glaucaPlant
Annona squamosaFooDB
Glycyrrhiza glabraPlant
Glycyrrhiza lepidotaPlant
Glycyrrhiza uralensisLOTUS Database
Helichrysum forskahliiPlant
Piscidia erythrinaPlant
Piscidia piscipulaPlant
Sophora tomentosaLOTUS Database
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
    • 

  • 2-furanone
    • 

  • Dihydrofuran
    • 

  • Tetrahydrofuran
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Polyol
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • 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
logP7.02ALOGPS
logP8.23ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)13.69ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity179.66 m³·mol⁻¹ChemAxon
Polarizability77.76 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032104  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008824  
KNApSAcK IDC00000965  
Chemspider IDNot Available
KEGG Compound IDC09752  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751256  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]