NP-MRD: Showing NP-Card for Continentalic acid (NP0141131)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-06-29 22:12:32 UTC

Updated at

2022-06-29 22:12:32 UTC

NP-MRD ID

NP0141131

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Continentalic acid

Description

Continentalic acid, also known as continentalate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Continentalic acid is found in Aldama arenaria, Aralia continentalis, Aralia cordata, Eleutherococcus trifoliatus, Herbertus dicranus, Mastigophora diclados, Pseudognaphalium gaudichaudianum, Sideritis discolor and Viguiera arenaria. It was first documented in 2020 (PMID: 33239093). Based on a literature review a significant number of articles have been published on Continentalic acid (PMID: 34833935) (PMID: 33711550) (PMID: 32448886) (PMID: 32004924).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    3.8069    1.1198   -1.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8978    1.0603   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819   -0.1215    0.1213 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6849   -0.9682    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -0.9581   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713   -0.8746   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438   -1.7516   -1.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -1.8950   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705   -0.6457    0.1202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7251    0.5247    0.1530 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5755    1.2542   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2604    1.4890    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947    1.2363    1.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5321    0.9106    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0505   -0.3105   -0.3743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9694   -1.4585    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2116   -0.1145   -1.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284    0.9992   -2.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470   -1.0587   -2.7883 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6021    0.0345    0.6619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5851    1.1096    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    0.4006    1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228    2.0029   -2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095    0.2718   -2.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2935    1.9028   -0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7268   -1.9021   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -1.3189    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229   -0.4216    0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507   -1.6428   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -2.7574   -1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -1.4482   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935   -2.3148   -1.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9883   -2.7322    0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8380   -0.8726    1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046    1.4441   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9082    0.6880   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0550    2.2555   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1579    2.5385    0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6872    1.3992    2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    0.4821    2.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0981    2.1863    1.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5442    1.8064   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5892    0.7816    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626   -2.1588   -0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5367   -1.9515    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9663   -1.0499    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1798   -0.8968   -3.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3995   -0.4919    1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2666    1.7982    1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9104    1.7259    0.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5431    1.1439    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6191   -0.4494    2.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3 22  1  0
 22 21  1  0
 21 20  1  0
 20  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  6
 17 19  1  0
 17 18  2  0
  6  5  2  0
  3  2  1  6
  2  1  2  3
  5  3  1  0
 10 20  1  0
 15  9  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
 22 51  1  0
 22 52  1  0
 21 49  1  0
 21 50  1  0
 20 48  1  1
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 19 47  1  0
  5 29  1  0
  2 25  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652306302200122D          

 22 24  0  0  1  0            999 V2000
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3689    2.3887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    1.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4217    0.1644    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 20  1  1  0  0  0
  2 21  1  1  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0141131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CC[C@@H]2C(CC[C@H]3[C@@]2(C)CCC[C@@]3(C)C(O)=O)=C1)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20-/m1/s1

> <INCHI_KEY>
MHVJRKBZMUDEEV-XIHRTOKZSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

$$$$

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       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.689   4.459   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.102   2.197   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.121   0.307   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    5   12   20                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11                                                            
CONECT   21    2   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Continentalate	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]1(CC[C@@H]2C(CC[C@H]3[C@@]2(C)CCC[C@@]3(C)C(O)=O)=C1)C=C

InChI Identifier

InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20-/m1/s1

InChI Key

MHVJRKBZMUDEEV-XIHRTOKZSA-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
Aldama arenaria	LOTUS Database	35616633
Aralia continentalis	LOTUS Database	35616633
Aralia cordata	LOTUS Database	35616633
Eleutherococcus trifoliatus	LOTUS Database	35616633
Herbertus dicranus	LOTUS Database	35616633
Mastigophora diclados	LOTUS Database	35616633
Pseudognaphalium gaudichaudianum	LOTUS Database	35616633
Sideritis discolor	LOTUS Database	35616633
Viguiera arenaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Pimarane diterpenoid
Diterpenoid
Phenanthrene
Hydrophenanthrene
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

8261833

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10086296

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jeon BE, Kwon CS, Lee JE, Moon K, Cha J, Park I, Koh S, Yoon M, Kim SW, Kim JN: Anticancer Activity of Continentalic Acid in B-Cell Lymphoma. Molecules. 2021 Nov 12;26(22):6845. doi: 10.3390/molecules26226845. [PubMed:34833935 ]
Liaquat I, Khan AU, Khan S: Pharmacological evaluation of continentalic acid for antidiabetic potential. Biomed Pharmacother. 2021 Jun;138:111411. doi: 10.1016/j.biopha.2021.111411. Epub 2021 Mar 9. [PubMed:33711550 ]
Ali H, Khan A, Ali J, Ullah H, Khan A, Ali H, Irshad N, Khan S: Attenuation of LPS-induced acute lung injury by continentalic acid in rodents through inhibition of inflammatory mediators correlates with increased Nrf2 protein expression. BMC Pharmacol Toxicol. 2020 Nov 25;21(1):81. doi: 10.1186/s40360-020-00458-7. [PubMed:33239093 ]
Lee JS, Quilantang NG, Hahm DH, Kang KS, Jacinto SD, Choi YJ, Lee SC, Lee S: Optimization of Extraction Conditions of Continentalic and Kaurenoic Acids from Aralia continentalis by HPLC/UV and Their Validation. J Chromatogr Sci. 2020 Jul 24;58(7):672-677. doi: 10.1093/chromsci/bmaa019. [PubMed:32448886 ]
Khan AM, Khan AU, Ali H, Islam SU, Seo EK, Khan S: Continentalic acid exhibited nephroprotective activity against the LPS and E. coli-induced kidney injury through inhibition of the oxidative stress and inflammation. Int Immunopharmacol. 2020 Mar;80:106209. doi: 10.1016/j.intimp.2020.106209. Epub 2020 Jan 28. [PubMed:32004924 ]

Showing NP-Card for Continentalic acid (NP0141131)

MOL for NP0141131 (Continentalic acid)

3D MOL for NP0141131 (Continentalic acid)

3D SDF for NP0141131 (Continentalic acid)

3D-SDF for NP0141131 (Continentalic acid)

PDB for NP0141131 (Continentalic acid)

3D PDB for NP0141131 (Continentalic acid)

SMILES for NP0141131 (Continentalic acid)

INCHI for NP0141131 (Continentalic acid)

Structure for NP0141131 (Continentalic acid)

3D Structure for NP0141131 (Continentalic acid)