NP-MRD: Showing NP-Card for 2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione (NP0299845)

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Record Information

Version

1.0

Created at

2022-09-10 11:54:54 UTC

Updated at

2022-09-10 11:54:54 UTC

NP-MRD ID

NP0299845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione

Description

2-Hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]Tridecan]-4'(13')-ene-3',6'-dione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione is found in Trichoderma gamsii. Based on a literature review very few articles have been published on 2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]Tridecan]-4'(13')-ene-3',6'-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102213542D          

 30 33  0  0  0  0            999 V2000
    4.2974    2.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7067    1.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9300    0.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213    0.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3266    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512    0.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8376    0.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6709    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    1.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238   -0.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.6614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011   -1.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309102213542D          

 30 33  0  0  0  0            999 V2000
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    3.7067    1.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0299845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC1N=C(O)C2(C1C(C)C(C)=O)C1=C3C(CC2=O)CCCCC3(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H33NO5/c1-12(2)10-16-18(13(3)14(4)26)24(22(29)25-16)17(27)11-15-8-6-7-9-23(5)19(15)20(24)21(28)30-23/h12-13,15-16,18H,6-11H2,1-5H3,(H,25,29)

> <INCHI_KEY>
WCSLFRZXNQREDG-UHFFFAOYSA-N

> <FORMULA>
C24H33NO5

> <MOLECULAR_WEIGHT>
415.53

> <EXACT_MASS>
415.235873167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.85299514443432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0^{4,13}]tridecan]-4'(13')-ene-3',6'-dione

> <JCHEM_LOGP>
2.5514878978573132

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.175258680807325

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3566852991638965

> <JCHEM_PKA_STRONGEST_BASIC>
5.314133874369629

> <JCHEM_POLAR_SURFACE_AREA>
93.03

> <JCHEM_REFRACTIVITY>
112.11379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0^{4,13}]tridecan]-4'(13')-ene-3',6'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.022   4.356   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.919   3.281   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.437   3.699   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.336   1.641   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.640   1.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.076   0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.616   0.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.897   1.304   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.452   1.176   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.328   2.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.111  -0.216   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.048  -1.235   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.775  -2.102   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.224  -3.630   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.557  -1.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.192  -2.656   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.037  -4.067   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.714  -3.088   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.512  -2.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.078  -2.562   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.745  -1.793   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.515  -0.270   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.562   0.859   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.098   0.744   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.106   2.295   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.040   1.963   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.490   1.443   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.967   2.566   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.444  -0.096   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.966  -0.528   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16   29                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   30                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   15   30                                                  
CONECT   30   29   19   24                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₃NO₅

Average Mass

415.5300 Da

Monoisotopic Mass

415.23587 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)CC1N=C(O)C2(C1C(C)C(C)=O)C1=C3C(CC2=O)CCCCC3(C)OC1=O

InChI Identifier

InChI=1S/C24H33NO5/c1-12(2)10-16-18(13(3)14(4)26)24(22(29)25-16)17(27)11-15-8-6-7-9-23(5)19(15)20(24)21(28)30-23/h12-13,15-16,18H,6-11H2,1-5H3,(H,25,29)

InChI Key

WCSLFRZXNQREDG-UHFFFAOYSA-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
Trichoderma gamsii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Cyclohexenone
2-furanone
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrroline
Dihydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162985881

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione (NP0299845)

MOL for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

3D MOL for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

3D SDF for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

3D-SDF for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

PDB for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

3D PDB for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

SMILES for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

INCHI for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

Structure for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)

3D Structure for NP0299845 (2-hydroxy-1'-methyl-5-(2-methylpropyl)-4-(3-oxobutan-2-yl)-4,5-dihydro-2'-oxaspiro[pyrrole-3,5'-tricyclo[6.4.1.0⁴,¹³]tridecan]-4'(13')-ene-3',6'-dione)