NP-MRD: Showing NP-Card for Isocoronarin D (NP0141153)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-06-29 22:13:42 UTC

Updated at

2022-06-29 22:13:42 UTC

NP-MRD ID

NP0141153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isocoronarin D

Description

Isocoronarin D 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. Isocoronarin D is found in Alpinia calcarata and Hedychium coronarium. It was first documented in 2015 (PMID: 25464007). Based on a literature review a significant number of articles have been published on isocoronarin D (PMID: 32354114) (PMID: 34143941) (PMID: 33759661) (PMID: 30453782).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    1.4833   -1.9092   -1.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -1.0414   -1.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7138   -1.3445   -2.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869   -1.1486   -1.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9572    0.1296   -0.8316 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2345    0.4864   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6958    1.8710   -0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3466   -0.4707   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2214    0.4419    1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143    1.0524    1.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8713    1.2973    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536    0.1245    0.0926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6303   -1.1355    0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535    0.2196   -0.8165 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6584    0.7682   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.1413    0.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5974   -0.0708    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3863   -0.6988    2.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -1.3948    2.9160 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7261   -0.3598    1.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396    0.5873    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    0.2420   -0.1200 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9025   -0.8867   -0.8811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3845   -1.8082   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922   -2.8311   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397   -2.3968   -2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6431   -0.7052   -3.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2719   -2.0419   -1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8047   -1.0350   -2.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    0.9309   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7144    1.8990   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    2.2759   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5962    2.5960    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1314   -1.5072   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5926   -0.3240   -1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2739   -0.1582   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1130    1.0526    1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4575   -0.5860    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503    2.0561    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7409    0.4273    2.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376    2.2542    0.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0662    1.4069    1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5519   -1.7712    0.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915   -0.9312    2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -1.8123    0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354    0.9916   -1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4138    1.8401    0.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075    0.9113   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857   -0.2017    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    1.6213    1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7758    0.5133    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3794    1.0673   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576   -0.6345   -1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 22  1  0
 22 23  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 14  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5 12  1  0
 18 17  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  6
 15 47  1  0
 15 48  1  0
 16 49  1  0
 22 52  1  6
 23 53  1  0
 21 50  1  0
 21 51  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
M  END


  Mrv1652306302200132D          

 23 25  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  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  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 21  1  0  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H](C\C=C3/C(O)COC3=O)C(=C)CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-13-6-9-17-19(2,3)10-5-11-20(17,4)15(13)8-7-14-16(21)12-23-18(14)22/h7,15-17,21H,1,5-6,8-12H2,2-4H3/b14-7+/t15-,16?,17-,20+/m0/s1

> <INCHI_KEY>
WCYYIFXENZTEHA-AIWPHDBSSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

$$$$

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.580  -7.835   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -9.300   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.564  -9.300   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.088  -7.835   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.377  -7.359   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.044  -7.359   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22   23                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22    6                                                            
CONECT   23    6                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H](C\C=C3/C(O)COC3=O)C(=C)CC[C@@H]12

InChI Identifier

InChI=1S/C20H30O3/c1-13-6-9-17-19(2,3)10-5-11-20(17,4)15(13)8-7-14-16(21)12-23-18(14)22/h7,15-17,21H,1,5-6,8-12H2,2-4H3/b14-7+/t15-,16?,17-,20+/m0/s1

InChI Key

WCYYIFXENZTEHA-AIWPHDBSSA-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
Alpinia calcarata	LOTUS Database	35616633
Hedychium coronarium	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

Gamma butyrolactone
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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

C00046779

Chemspider ID

28424510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71550939

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tavares WR, Barreto MDC, Seca AML: Uncharted Source of Medicinal Products: The Case of the Hedychium Genus. Medicines (Basel). 2020 Apr 28;7(5). pii: medicines7050023. doi: 10.3390/medicines7050023. [PubMed:32354114 ]
Zeng QH, Lu CL, Zhang XW, Jiang JG: Isolation and identification of ingredients inducing cancer cell death from the seeds of Alpinia galanga, a Chinese spice. Food Funct. 2015 Feb;6(2):431-43. doi: 10.1039/c4fo00709c. [PubMed:25464007 ]
Subramanyan S, Deepika S, Ajith A, Joseph Gracy A, Dan M, Maiti KK, Varma RL, Radhakrishnan KV: Antiproliferative labdane diterpenes from the rhizomes of Hedychium flavescens Carey ex Roscoe. Chem Biol Drug Des. 2021 Oct;98(4):501-506. doi: 10.1111/cbdd.13906. Epub 2021 Jun 29. [PubMed:34143941 ]
Lu CL, Wang LN, Li YJ, Fan QF, Huang QH, Chen JJ: Anti-hyperglycaemic effect of labdane diterpenes isolated from the rhizome of Amomum maximum Roxb., an edible plant in Southwest China. Nat Prod Res. 2022 May;36(10):2570-2574. doi: 10.1080/14786419.2021.1903006. Epub 2021 Mar 24. [PubMed:33759661 ]
Chokchaisiri R, Chaichompoo W, Sukcharoen O, Suksamrarn A, Ganranoo L: Microbial transformation of isocoronarin D by Cunninghamella echinulata NRRL 1386. Nat Prod Res. 2019 Oct;33(20):2890-2896. doi: 10.1080/14786419.2018.1509331. Epub 2018 Nov 20. [PubMed:30453782 ]

Showing NP-Card for Isocoronarin D (NP0141153)

MOL for NP0141153 (Isocoronarin D)

3D MOL for NP0141153 (Isocoronarin D)

3D SDF for NP0141153 (Isocoronarin D)

3D-SDF for NP0141153 (Isocoronarin D)

PDB for NP0141153 (Isocoronarin D)

3D PDB for NP0141153 (Isocoronarin D)

SMILES for NP0141153 (Isocoronarin D)

INCHI for NP0141153 (Isocoronarin D)

Structure for NP0141153 (Isocoronarin D)

3D Structure for NP0141153 (Isocoronarin D)