NP-MRD: Showing NP-Card for (z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione (NP0172041)

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Record Information

Version

2.0

Created at

2022-09-03 08:49:23 UTC

Updated at

2022-09-03 08:49:23 UTC

NP-MRD ID

NP0172041

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione

Description

Terrestric acid, also known as terrestrate, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione is found in Pyricularia grisea and Penicillium solitum. (z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione was first documented in 2019 (PMID: 31432669). Based on a literature review a small amount of articles have been published on Terrestric acid (PMID: 32967562) (PMID: 34761275) (PMID: 31971016) (PMID: 31833773).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.1604   -0.4054    0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7701    0.0045    1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0573    0.5461    0.0529 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9568   -0.4936   -1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301   -1.1658   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1686    0.0251   -0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4529    0.2634   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2650    1.4099   -0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7674    2.4263    0.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923    1.2263   -0.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7463   -0.1613   -0.6497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2121   -0.7845    0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020   -0.6684   -1.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053   -1.6501   -1.7814 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181    0.9102    0.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661   -1.4781    0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    0.1614    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -0.1541   -0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379    0.7995    2.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2044   -0.8472    1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5701    1.4693   -0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8117   -0.0332   -2.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915   -1.2230   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121   -1.7293   -1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8651   -1.7930    0.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4434   -0.3647   -1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3306   -0.8710    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371   -1.7360    0.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0300   -0.1082    1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 15  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 15  3  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  6
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 12 29  1  0
M  END


  Mrv1652309032210492D          

 15 16  0  0  1  0            999 V2000
    2.7343    2.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    1.3443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6873    0.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    0.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073    0.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224   -0.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974   -0.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    0.0747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -1.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099   -1.8623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7099   -2.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773   -1.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1620   -1.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    0.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 15  1  0  0  0  0
  3 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172041

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CC\C(O1)=C1\C(=O)O[C@H](C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O4/c1-3-7-4-5-8(15-7)9-10(12)6(2)14-11(9)13/h6-7H,3-5H2,1-2H3/b9-8-/t6-,7+/m1/s1

> <INCHI_KEY>
AABWXKZJSNWRSH-PNZIDKJXSA-N

> <FORMULA>
C11H14O4

> <MOLECULAR_WEIGHT>
210.229

> <EXACT_MASS>
210.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.623878867504658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(Z,5S,5'R)-5-ethyl-5'-methyl-3,4-dihydro-2'H,4'H,5H,5'H-[2,3'-bioxolylidene]-2',4'-dione

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
1.681977784666667

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.50741302199582

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8607509353429394

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
53.903900000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z,5S,5'R)-5-ethyl-5'-methyl-4,5-dihydro-3H,5'H-[2,3'-bioxolylidene]-2',4'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       5.104   4.819   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.770   4.049   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.770   2.509   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.016   1.604   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.540   0.139   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.000   0.139   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.095  -1.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.555  -1.106   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.350   0.139   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.079  -2.571   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.325  -3.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.325  -5.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.571  -2.571   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.036  -3.047   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.524   1.604   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13                                                            
CONECT   15    6    3                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
Terrestrate	Generator

Chemical Formula

C₁₁H₁₄O₄

Average Mass

210.2290 Da

Monoisotopic Mass

210.08921 Da

IUPAC Name

(Z,5S,5'R)-5-ethyl-5'-methyl-3,4-dihydro-2'H,4'H,5H,5'H-[2,3'-bioxolylidene]-2',4'-dione

Traditional Name

(Z,5S,5'R)-5-ethyl-5'-methyl-4,5-dihydro-3H,5'H-[2,3'-bioxolylidene]-2',4'-dione

CAS Registry Number

Not Available

SMILES

CC[C@H]1CC\C(O1)=C1\C(=O)O[C@H](C)C1=O

InChI Identifier

InChI=1S/C11H14O4/c1-3-7-4-5-8(15-7)9-10(12)6(2)14-11(9)13/h6-7H,3-5H2,1-2H3/b9-8-/t6-,7+/m1/s1

InChI Key

AABWXKZJSNWRSH-PNZIDKJXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Magnaporthe grisea	LOTUS Database	35616633
Penicillium solitum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

3-furanone
Gamma butyrolactone
Oxolane
Enoate ester
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.46	ALOGPS
logP	1.68	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.51	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	53.9 m³·mol⁻¹	ChemAxon
Polarizability	21.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2299365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3035039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El-Kashef DH, Daletos G, Plenker M, Hartmann R, Mandi A, Kurtan T, Weber H, Lin W, Ancheeva E, Proksch P: Polyketides and a Dihydroquinolone Alkaloid from a Marine-Derived Strain of the Fungus Metarhizium marquandii. J Nat Prod. 2019 Sep 27;82(9):2460-2469. doi: 10.1021/acs.jnatprod.9b00125. Epub 2019 Aug 21. [PubMed:31432669 ]
Duduk N, Bekcic F, Zebeljan A, Vuckovic N, Vico I: First report of blue mold caused by Penicillium crustosum on nectarine fruit in Serbia. Plant Dis. 2020 Sep 23. doi: 10.1094/PDIS-07-20-1632-PDN. [PubMed:32967562 ]
Zhou J, Li SM: Conversion of viridicatic acid to crustosic acid by cytochrome P450 enzyme-catalysed hydroxylation and spontaneous cyclisation. Appl Microbiol Biotechnol. 2021 Dec;105(24):9181-9189. doi: 10.1007/s00253-021-11674-4. Epub 2021 Nov 11. [PubMed:34761275 ]
Ngwoke KG, El-Kashef DH, Daletos G, Ancheeva E, Liu Z, Okoye FBC, Esimone CO, Proksch P: R-Hexitronic acid, a new tetronic acid derivative isolated from a soil fungus FG9RK. Nat Prod Res. 2021 Nov;35(21):3578-3583. doi: 10.1080/14786419.2020.1715400. Epub 2020 Jan 23. [PubMed:31971016 ]
Fan J, Liao G, Ludwig-Radtke L, Yin WB, Li SM: Formation of Terrestric Acid in Penicillium crustosum Requires Redox-Assisted Decarboxylation and Stereoisomerization. Org Lett. 2020 Jan 3;22(1):88-92. doi: 10.1021/acs.orglett.9b04002. Epub 2019 Dec 13. [PubMed:31833773 ]
LOTUS database [Link]

Showing NP-Card for (z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione (NP0172041)

MOL for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

3D MOL for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

3D SDF for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

3D-SDF for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

PDB for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

3D PDB for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

SMILES for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

INCHI for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

Structure for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)

3D Structure for NP0172041 ((z,5s,5'r)-5-ethyl-5'-methyl-4,5-dihydro-3h,5'h-[2,3'-bioxolylidene]-2',4'-dione)