NP-MRD: Showing NP-Card for (3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione (NP0226457)

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Record Information

Version

2.0

Created at

2022-09-06 05:30:10 UTC

Updated at

2022-09-06 05:30:10 UTC

NP-MRD ID

NP0226457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione

Description

Cochliospicin A belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione is found in Curvularia spicifera. Based on a literature review very few articles have been published on Cochliospicin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207302D          

 23 25  0  0  1  0            999 V2000
   -1.2314   -3.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4868   -3.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4222   -2.5590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2434   -2.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3766   -2.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -3.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9547   -2.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7341   -1.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0646   -1.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428   -1.7640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2793   -2.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9752   -1.8457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7427   -2.1482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7687   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936   -0.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453   -0.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3123   -0.7934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0917    0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111   -0.9999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6892   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -1.7948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535   -2.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  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
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  6  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(C)C(=O)C2=C([C@@H](C)[C@@H](C)OC2)C(=O)[C@]11C[C@@H](O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O6/c1-5-16(4)13(19)10-7-22-9(3)8(2)12(10)14(20)17(16)6-11(18)15(21)23-17/h8-9,11,18H,5-7H2,1-4H3/t8-,9+,11+,16-,17+/m0/s1

> <INCHI_KEY>
YXBCBQJJLPBBMD-IWFFIOHPSA-N

> <FORMULA>
C17H22O6

> <MOLECULAR_WEIGHT>
322.357

> <EXACT_MASS>
322.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.92398978215125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R,4'R,6S,7R)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-1,3,4,5,7,8-hexahydrospiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione

> <JCHEM_LOGP>
1.7566536326666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.586687466701822

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8543829020646223

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
80.83249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,4'R,6S,7R)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1H-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.299  -6.975   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.909  -6.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.788  -4.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.321  -4.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.703  -5.162   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.115  -6.646   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.782  -4.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.370  -2.580   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.121  -2.194   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.532  -0.710   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.200  -3.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.388  -4.273   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.687  -3.445   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.120  -4.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.302  -1.954   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.281  -0.766   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.764  -1.860   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.450  -1.481   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.038   0.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.941  -1.866   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.020  -0.768   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.352  -3.350   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.273  -4.449   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12   17                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11                                                       
CONECT   18    8   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    7                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₆

Average Mass

322.3570 Da

Monoisotopic Mass

322.14164 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@@]1(C)C(=O)C2=C([C@@H](C)[C@@H](C)OC2)C(=O)[C@]11C[C@@H](O)C(=O)O1

InChI Identifier

InChI=1S/C17H22O6/c1-5-16(4)13(19)10-7-22-9(3)8(2)12(10)14(20)17(16)6-11(18)15(21)23-17/h8-9,11,18H,5-7H2,1-4H3/t8-,9+,11+,16-,17+/m0/s1

InChI Key

YXBCBQJJLPBBMD-IWFFIOHPSA-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
Cochliobolus spicifer	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Cyclohexenone
Alpha-acyloxy ketone
Gamma butyrolactone
Pyran
Oxolane
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
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

C00050039

Chemspider ID

8743219

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10567832

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione (NP0226457)

MOL for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

3D MOL for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

3D SDF for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

3D-SDF for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

PDB for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

3D PDB for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

SMILES for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

INCHI for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

Structure for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)

3D Structure for NP0226457 ((3r,4r,4'r,6s,7r)-7-ethyl-4'-hydroxy-3,4,7-trimethyl-3,4-dihydro-1h-spiro[2-benzopyran-6,2'-oxolane]-5,5',8-trione)