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Showing NP-Card for (-)-Terreic acid (NP0062240)

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Record Information
Version1.0
Created at2022-04-28 06:54:32 UTC
Updated at2022-04-28 06:54:32 UTC
NP-MRD IDNP0062240
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Terreic acid
DescriptionTerreic acid, also known as terreate or versilin, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (-)-Terreic acid is found in Aspergillus flavipes and Aspergillus terreus 5378 . It was first documented in 2016 (PMID: 27455860). Based on a literature review a significant number of articles have been published on Terreic acid (PMID: 29391515) (PMID: 29251283) (PMID: 29186697) (PMID: 26762501).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0062240 ((-)-Terreic acid)


  Mrv1652304282208542D          

 11 12  0  0  1  0            999 V2000
    0.4763   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  5 10  1  0  0  0  0
  2 11  1  1  0  0  0
  1 11  1  1  0  0  0
M  END
Download

3D MOL for NP0062240 ((-)-Terreic acid)

     RDKit          3D

 17 18  0  0  0  0  0  0  0  0999 V2000
    2.1345   -0.3684   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7142   -0.1507   -0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3201    0.9964    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    1.9907    0.4349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0981    1.1838    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5277    2.3618    0.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122    0.0426    0.6072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4831   -1.0318    1.4770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.1517    0.0162 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3289   -1.1573   -0.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379   -2.0339   -1.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250    0.0063   -1.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784   -1.4524   -0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7334    0.1595    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103    2.2848    1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288    0.2705    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -1.9501   -0.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10  2  1  0
  9  7  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  7 16  1  1
  9 17  1  1
M  END
Download

3D SDF for NP0062240 ((-)-Terreic acid)


  Mrv1652304282208542D          

 11 12  0  0  1  0            999 V2000
    0.4763   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  5 10  1  0  0  0  0
  2 11  1  1  0  0  0
  1 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062240

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(=O)[C@@H]2O[C@@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1

> <INCHI_KEY>
ATFNSNUJZOYXFC-RQJHMYQMSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.413940800137095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
0.2748246343333334

> <ALOGPS_LOGS>
0.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.94808234332145

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.478417529922911

> <JCHEM_PKA_STRONGEST_BASIC>
-4.320529302381678

> <JCHEM_POLAR_SURFACE_AREA>
66.89999999999999

> <JCHEM_REFRACTIVITY>
35.449600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0062240 ((-)-Terreic acid)

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PDB for NP0062240 ((-)-Terreic acid)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.889  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.223   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.556  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.556  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.223  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.223  -3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.890  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.890   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.445  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10    5                                                            
CONECT   11    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0062240 ((-)-Terreic acid)
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SMILES for NP0062240 ((-)-Terreic acid)
CC1=C(O)C(=O)[C@@H]2O[C@@H]2C1=O
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INCHI for NP0062240 ((-)-Terreic acid)
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
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View in JSmol
Synonyms
ValueSource
TerreateGenerator
Terreic acid, (+-)-isomerMeSH
Terreic acid, (1S)-isomerMeSH
VersilinMeSH
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
IUPAC Name(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Traditional Name(1R,6S)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
CAS Registry NumberNot Available
SMILES
CC1=C(O)C(=O)[C@@H]2O[C@@H]2C1=O
InChI Identifier
InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
InChI KeyATFNSNUJZOYXFC-RQJHMYQMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus flavipesLOTUS Database
Aspergillus terreus 5378Fungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclohexenones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Vinylogous acid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Enol
    • 

  • Dialkyl ether
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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-0.19ALOGPS
logP0.27ChemAxon
logS0.48ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.45 m³·mol⁻¹ChemAxon
Polarizability13.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018689  
Chemspider ID82566  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91437  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kong C, Huang H, Xue Y, Liu Y, Peng Q, Liu Q, Xu Q, Zhu Q, Yin Y, Zhou X, Zhang Y, Cai M: Heterologous pathway assembly reveals molecular steps of fungal terreic acid biosynthesis. Sci Rep. 2018 Feb 1;8(1):2116. doi: 10.1038/s41598-018-20514-x. [PubMed:29391515  ] 
  2. Ferguson LB, Ozburn AR, Ponomarev I, Metten P, Reilly M, Crabbe JC, Harris RA, Mayfield RD: Genome-Wide Expression Profiles Drive Discovery of Novel Compounds that Reduce Binge Drinking in Mice. Neuropsychopharmacology. 2018 May;43(6):1257-1266. doi: 10.1038/npp.2017.301. Epub 2017 Dec 18. [PubMed:29251283  ] 
  3. Sarnoski EA, Liu P, Acar M: A High-Throughput Screen for Yeast Replicative Lifespan Identifies Lifespan-Extending Compounds. Cell Rep. 2017 Nov 28;21(9):2639-2646. doi: 10.1016/j.celrep.2017.11.002. [PubMed:29186697  ] 
  4. Yin Y, Cai M, Zhou X, Li Z, Zhang Y: Polyketides in Aspergillus terreus: biosynthesis pathway discovery and application. Appl Microbiol Biotechnol. 2016 Sep;100(18):7787-98. doi: 10.1007/s00253-016-7733-z. Epub 2016 Jul 26. [PubMed:27455860  ] 
  5. Sharma R, Lambu MR, Jamwal U, Rani C, Chib R, Wazir P, Mukherjee D, Chaubey A, Khan IA: Escherichia coli N-Acetylglucosamine-1-Phosphate-Uridyltransferase/Glucosamine-1-Phosphate-Acetylt ransferase (GlmU) Inhibitory Activity of Terreic Acid Isolated from Aspergillus terreus. J Biomol Screen. 2016 Apr;21(4):342-53. doi: 10.1177/1087057115625308. Epub 2016  Jan 13. [PubMed:26762501  ]