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Showing NP-Card for Ligupurpuroside J (NP0044157)

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Record Information
Version1.0
Created at2021-11-12 23:53:24 UTC
Updated at2021-11-26 17:46:04 UTC
NP-MRD IDNP0044157
Secondary Accession NumbersNone
Natural Product Identification
Common NameLigupurpuroside J
DescriptionAsperochrin B 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. Ligupurpuroside J is found in Aspergillus ochraceus. It was first documented in 2021 (PMID: 34758541). Based on a literature review a significant number of articles have been published on Asperochrin B (PMID: 34758536) (PMID: 34758492) (PMID: 34758485) (PMID: 34758461).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044157 (Ligupurpuroside J)


  Mrv1652311132100532D          

 13 13  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5911   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  6  0  0  0
M  END
Download

3D MOL for NP0044157 (Ligupurpuroside J)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -3.6647    1.1249    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1299   -0.0862    0.1541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9635    0.3124   -0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944   -0.3722   -0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4740   -0.2499   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    0.1493    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    0.3323    1.3331 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8740    0.3235   -0.1860 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3907   -0.9715   -0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6683    0.6977    0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967   -1.2719    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -2.1025    1.4385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6447   -1.0654    1.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7774    1.9341    0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407    1.4601    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6135    0.8159    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -0.4611   -0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9870    1.0703   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452    0.4568   -1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726   -1.2365   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9107    1.1582   -0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4922   -0.7807   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.7998   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366   -1.1011   -1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7693    1.6634    0.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 13  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  6
  3 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  6
  9 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
M  END
Download

3D SDF for NP0044157 (Ligupurpuroside J)


  Mrv1652311132100532D          

 13 13  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5911   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)C(=O)CC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O4/c1-5-3-7(9(12)13-5)4-8(11)6(2)10/h3,5-6,10H,4H2,1-2H3/t5-,6-/m0/s1

> <INCHI_KEY>
XFFVATGTKQPOOV-WDSKDSINSA-N

> <FORMULA>
C9H12O4

> <MOLECULAR_WEIGHT>
184.191

> <EXACT_MASS>
184.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.267836944814533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-3-[(3S)-3-hydroxy-2-oxobutyl]-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
0.5542097216666675

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.370349692419303

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.972229785121275

> <JCHEM_PKA_STRONGEST_BASIC>
-3.365545677529071

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
46.03690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(3S)-3-hydroxy-2-oxobutyl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0044157 (Ligupurpuroside J)

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PDB for NP0044157 (Ligupurpuroside J)
HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.267  -1.375   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.893   0.032   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.172  -2.621   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.703  -2.460   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.545  -4.027   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    2                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0044157 (Ligupurpuroside J)
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SMILES for NP0044157 (Ligupurpuroside J)
C[C@H](O)C(=O)CC1=C[C@H](C)OC1=O
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INCHI for NP0044157 (Ligupurpuroside J)
InChI=1S/C9H12O4/c1-5-3-7(9(12)13-5)4-8(11)6(2)10/h3,5-6,10H,4H2,1-2H3/t5-,6-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H12O4
Average Mass184.1910 Da
Monoisotopic Mass184.07356 Da
IUPAC Name(5S)-3-[(3S)-3-hydroxy-2-oxobutyl]-5-methyl-2,5-dihydrofuran-2-one
Traditional Name(5S)-3-[(3S)-3-hydroxy-2-oxobutyl]-5-methyl-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
C[C@H](O)C(=O)CC1=C[C@H](C)OC1=O
InChI Identifier
InChI=1S/C9H12O4/c1-5-3-7(9(12)13-5)4-8(11)6(2)10/h3,5-6,10H,4H2,1-2H3/t5-,6-/m0/s1
InChI KeyXFFVATGTKQPOOV-WDSKDSINSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus ochraceusLOTUS 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
    • 

  • 2-furanone
    • 

  • Acyloin
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Dihydrofuran
    • 

  • Alpha-hydroxy ketone
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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
logP-0.45ALOGPS
logP0.55ChemAxon
logS-0.6ALOGPS
pKa (Strongest Acidic)9.97ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.04 m³·mol⁻¹ChemAxon
Polarizability18.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID40256808  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122206500  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dai Y, Wang YH, An Y, Lu C, Zhang HH, Fan XT, Wei PH, Ren LK, Shan YZ, Zhao GG: [Observation of efficacy and safety of stereotactic-EEG-guided three-dimensional radiofrequency thermocoagulation for the treatment of drug-resistant insular epilepsy]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3386-3392. doi: 10.3760/cma.j.cn112137-20210505-01057. [PubMed:34758541  ] 
  2. Ren SQ, Wei Y, Wang YQ, Ou Y, Wang Q, Feng HL, Luo C, Nie Y, Lyu Q, Fan SD, Zhou F, Chen ZJ, Zhong S, Tian JZ, Wang D: [Comparison of single incision robot-assisted laparoscopic radical prostatectomy with and without extraperitoneal special channel device]. Zhonghua Yi Xue Za Zhi. 2021 Nov 2;101(40):3345-3350. doi: 10.3760/cma.j.cn112137-20210303-00545. [PubMed:34758536  ] 
  3. Khosravi M: A Possible Type IV Hypersensitivity Reaction to Older Antiepileptic Drugs During and After Recovery from COVID-19 Infection. Pharmacopsychiatry. 2021 Nov 10. doi: 10.1055/a-1678-7429. [PubMed:34758492  ] 
  4. She X, Berger TW, Song D: A Double-Layer, Multi-Resolution Classification Model for Decoding Spatiotemporal Patterns of Spikes with Small Sample Size. Neural Comput. 2021 Nov 4:1-36. doi: 10.1162/neco_a_01459. [PubMed:34758485  ] 
  5. Causa R, Almagro-Nievas D, Rivera-Izquierdo M, Benitez-Munoz N, Lopez-Hernandez B, Garcia-Garcia F, Alvarez-Estevez M, Soto-Perez MO, Bermudez-Tamayo C: Antibody Response 3 Months after 2 Doses of BNT162b2 mRNA COVID-19 Vaccine in Residents of Long-Term Care Facilities. Gerontology. 2021 Nov 10:1-7. doi: 10.1159/000519711. [PubMed:34758461  ] 
  6. Long Fan et al. (2015). Phenylethanoid and secoiridoid glycosides from the leaves of Ligustrum purpurascens. Phytochemistry Letters, Volume 13, September 2015, Pages 177-181. DOI: 10.1016/j.phytol.2015.06.011. Phytochemistry Letters.