NP-MRD: Showing NP-Card for Coronarin A (NP0141163)

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Record Information

Version

1.0

Created at

2022-06-29 22:14:10 UTC

Updated at

2022-06-29 22:14:11 UTC

NP-MRD ID

NP0141163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coronarin A

Description

Coronarin A belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Coronarin A is found in Hedychium coronarium and Hedychium gardnerianum. It was first documented in 2008 (PMID: 18310958). Based on a literature review a significant number of articles have been published on Coronarin A (PMID: 19960422) (PMID: 19385181) (PMID: 33968897) (PMID: 22293485).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    1.0642   -3.1237   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -1.9990   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6021   -2.0572    1.0827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0444   -2.6171    2.2236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1319   -0.6677    1.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5642   -0.1453   -0.0286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6402    0.8704    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9699    0.0928    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001    1.7128    1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6978    1.8028   -1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    1.3445   -2.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108    0.4251   -2.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3620    0.2573   -0.8640 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2545    1.5631   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454   -0.8380   -0.8696 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0237   -0.3531   -0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6874   -0.8002    0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0041   -0.2860    0.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944    0.6840    0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9134    0.8838    0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9699    0.0937    1.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8638   -0.6183    1.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215   -4.0154    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869   -3.1334   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877   -2.6618    0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -3.1570    2.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702   -0.0674    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -0.6528    2.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798   -1.0363   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783    0.8581    0.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.5633   -0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0645   -0.4566    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5213    2.8121    1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702    1.6620    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8362    1.3800    2.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3459    2.8380   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7926    1.9799   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8165    0.8814   -3.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119    2.2586   -2.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021   -0.6149   -2.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820    0.7024   -2.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471    2.2008   -1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    1.4045    0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    2.1264    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7494   -1.2560   -1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    0.4065   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595   -1.5462    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656    1.2096   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6968    1.5670    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -1.3506    2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  2 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 22  2  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
  6  7  1  0
 19 18  1  0
 15 13  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
  6 29  1  6
  5 27  1  0
  5 28  1  0
  3 25  1  6
  4 26  1  0
  1 23  1  0
  1 24  1  0
 15 45  1  6
 16 46  1  0
 17 47  1  0
 22 50  1  0
 20 49  1  0
 19 48  1  0
M  END


  Mrv1652306302200142D          

 22 24  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  1  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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -4.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  0  0  0  0
  9 20  1  6  0  0  0
  6 21  1  0  0  0  0
  6 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@H]1C[C@H](O)C(=C)[C@@H]2\C=C\C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-14-16(7-6-15-8-11-22-13-15)20(4)10-5-9-19(2,3)18(20)12-17(14)21/h6-8,11,13,16-18,21H,1,5,9-10,12H2,2-4H3/b7-6+/t16-,17-,18-,20+/m0/s1

> <INCHI_KEY>
RHCBUXSXDFNUAG-UDMCIFMYSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

$$$$

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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.247  -7.835   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.771  -9.300   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.231  -9.300   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   22  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   21   22                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
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                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20    9                                                            
CONECT   21    6                                                            
CONECT   22    6                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@H]1C[C@H](O)C(=C)[C@@H]2\C=C\C1=COC=C1

InChI Identifier

InChI=1S/C20H28O2/c1-14-16(7-6-15-8-11-22-13-15)20(4)10-5-9-19(2,3)18(20)12-17(14)21/h6-8,11,13,16-18,21H,1,5,9-10,12H2,2-4H3/b7-6+/t16-,17-,18-,20+/m0/s1

InChI Key

RHCBUXSXDFNUAG-UDMCIFMYSA-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
Hedychium coronarium	LOTUS Database	35616633
Hedychium gardnerianum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Heteroaromatic compound
Furan
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

C00032542

Chemspider ID

23153843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24851535

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kumrit I, Suksamrarn A, Meepawpan P, Songsri S, Nuntawong N: Labdane-type diterpenes from Hedychium gardnerianum with potent cytotoxicity against human small cell lung cancer cells. Phytother Res. 2010 Jul;24(7):1009-13. doi: 10.1002/ptr.3057. [PubMed:19960422 ]
Luo M, Lei L, Lin H: [Studies on chemical constituents from rhizomes of Hedychium chrysoleucum]. Zhongguo Zhong Yao Za Zhi. 2009 Jan;34(2):180-2. [PubMed:19385181 ]
Singamaneni V, Lone B, Singh J, Kumar P, Gairola S, Singh S, Gupta P: Coronarin K and L: Two Novel Labdane Diterpenes From Roscoea purpurea: An Ayurvedic Crude Drug. Front Chem. 2021 Apr 21;9:642073. doi: 10.3389/fchem.2021.642073. eCollection 2021. [PubMed:33968897 ]
Kiem PV, Anh Hle T, Nhiem NX, Minh CV, Thuy NT, Yen PH, Hang DT, Tai BH, Mathema VB, Koh YS, Kim YH: Labdane-type diterpenoids from the rhizomes of Hedychium coronarium inhibit lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Chem Pharm Bull (Tokyo). 2012;60(2):246-50. doi: 10.1248/cpb.60.246. [PubMed:22293485 ]
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Showing NP-Card for Coronarin A (NP0141163)

MOL for NP0141163 (Coronarin A)

3D MOL for NP0141163 (Coronarin A)

3D SDF for NP0141163 (Coronarin A)

3D-SDF for NP0141163 (Coronarin A)

PDB for NP0141163 (Coronarin A)

3D PDB for NP0141163 (Coronarin A)

SMILES for NP0141163 (Coronarin A)

INCHI for NP0141163 (Coronarin A)

Structure for NP0141163 (Coronarin A)

3D Structure for NP0141163 (Coronarin A)