NP-MRD: Showing NP-Card for Arjunic acid (NP0141088)

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Record Information

Version

2.0

Created at

2022-06-29 22:10:27 UTC

Updated at

2022-06-29 22:10:27 UTC

NP-MRD ID

NP0141088

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arjunic acid

Description

Arjunic acid, also known as arjunate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Arjunic acid is found in Markhamia lutea, Quercus macrocarpa, Eriobotrya deflexa, Rosa davidii, Terminalia alata and Terminalia arjuna. It was first documented in 2017 (PMID: 28924162). Based on a literature review a significant number of articles have been published on Arjunic acid (PMID: 30668318) (PMID: 33425648) (PMID: 33808219) (PMID: 33246123) (PMID: 31767507) (PMID: 31631709).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306302200102D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306302200102D          

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    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  2 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
 15 10  1  6  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
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 17 21  1  0  0  0  0
 16 22  1  6  0  0  0
 14 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 11 26  1  6  0  0  0
  6 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  1  0  0  0
 28 34  1  6  0  0  0
  6 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0141088

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O5/c1-25(2)12-14-30(24(34)35)15-13-28(6)17(21(30)23(25)33)8-9-20-27(5)16-18(31)22(32)26(3,4)19(27)10-11-29(20,28)7/h8,18-23,31-33H,9-16H2,1-7H3,(H,34,35)/t18-,19+,20-,21-,22+,23+,27+,28-,29-,30+/m1/s1

> <INCHI_KEY>
XJMYUPJDAFKICJ-YZTGESMESA-N

> <FORMULA>
C30H48O5

> <MOLECULAR_WEIGHT>
488.709

> <EXACT_MASS>
488.350174646

$$$$

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       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.650   2.920   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.397   3.643   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   27   35                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    2   12   26                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19   23                                             
CONECT   15   14   10   16                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   20   21                                             
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21   17                                                            
CONECT   22   16                                                            
CONECT   23   14   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   11                                                            
CONECT   27    6   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29    5   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   28                                                            
CONECT   35    6                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Arjunate	Generator

Chemical Formula

C₃₀H₄₈O₅

Average Mass

488.7090 Da

Monoisotopic Mass

488.35017 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@@H]1O)C(O)=O

InChI Identifier

InChI=1S/C30H48O5/c1-25(2)12-14-30(24(34)35)15-13-28(6)17(21(30)23(25)33)8-9-20-27(5)16-18(31)22(32)26(3,4)19(27)10-11-29(20,28)7/h8,18-23,31-33H,9-16H2,1-7H3,(H,34,35)/t18-,19+,20-,21-,22+,23+,27+,28-,29-,30+/m1/s1

InChI Key

XJMYUPJDAFKICJ-YZTGESMESA-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
Markhamia lutea	LOTUS Database	35616633
Quercus macrocarpa	LOTUS Database	35616633
Rhaphiolepis deflexa	LOTUS Database	35616633
Rosa davidii	LOTUS Database	35616633
Terminalia alata	LOTUS Database	35616633
Terminalia arjuna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

C00045579

Chemspider ID

10217402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15385516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mohanty IR, Borde M, Kumar C S, Maheshwari U: Dipeptidyl peptidase IV Inhibitory activity of Terminalia arjuna attributes to its cardioprotective effects in experimental diabetes: In silico, in vitro and in vivo analyses. Phytomedicine. 2019 Apr;57:158-165. doi: 10.1016/j.phymed.2018.09.195. Epub 2018 Sep 19. [PubMed:30668318 ]
Falade VA, Adelusi TI, Adedotun IO, Abdul-Hammed M, Lawal TA, Agboluaje SA: In silico investigation of saponins and tannins as potential inhibitors of SARS-CoV-2 main protease (M(pro)). In Silico Pharmacol. 2021 Jan 6;9(1):9. doi: 10.1007/s40203-020-00071-w. eCollection 2021. [PubMed:33425648 ]
Stepnik K: Biomimetic Chromatographic Studies Combined with the Computational Approach to Investigate the Ability of Triterpenoid Saponins of Plant Origin to Cross the Blood-Brain Barrier. Int J Mol Sci. 2021 Mar 30;22(7). pii: ijms22073573. doi: 10.3390/ijms22073573. [PubMed:33808219 ]
Balde MA, Tuenter E, Matheeussen A, Traore MS, Cos P, Maes L, Camara A, Diallo MST, Balde ES, Balde AM, Pieters L, Foubert K: Bioassay-guided isolation of antiplasmodial and antimicrobial constituents from the roots of Terminalia albida. J Ethnopharmacol. 2021 Mar 1;267:113624. doi: 10.1016/j.jep.2020.113624. Epub 2020 Nov 25. [PubMed:33246123 ]
T MM, T A, P BK, Fathima A, Khanum F: In-silico therapeutic investigations of arjunic acid and arjungenin as an FXR agonist and validation in 3T3-L1 adipocytes. Comput Biol Chem. 2020 Feb;84:107163. doi: 10.1016/j.compbiolchem.2019.107163. Epub 2019 Nov 15. [PubMed:31767507 ]
Ado MA, Maulidiani M, Ismail IS, Ghazali HM, Shaari K, Abas F: Acetylcholinesterase and alpha-glucosidase inhibitory compounds from Callicarpa maingayi. Nat Prod Res. 2021 Sep;35(17):2992-2996. doi: 10.1080/14786419.2019.1679138. Epub 2019 Oct 21. [PubMed:31631709 ]
Manu TM, Anand T, Pandareesh MD, Kumar PB, Khanum F: Terminalia arjuna extract and arjunic acid mitigate cobalt chloride-induced hypoxia stress-mediated apoptosis in H9c2 cells. Naunyn Schmiedebergs Arch Pharmacol. 2019 Sep;392(9):1107-1119. doi: 10.1007/s00210-019-01654-x. Epub 2019 May 8. [PubMed:31069430 ]
Khatkar S, Nanda A, Ansari SH: Comparative Evaluation of Conventional and Novel Extracts of Stem Bark of Terminalia arjuna for Antihypertensive Activity in BSO Induced Oxidative Stress based Rat Model. Curr Pharm Biotechnol. 2019;20(2):157-167. doi: 10.2174/1389201020666190222185209. [PubMed:30806310 ]
Kim S, Oh S, Noh HB, Ji S, Lee SH, Koo JM, Choi CW, Jhun HP: In Vitro Antioxidant and Anti-Propionibacterium acnes Activities of Cold Water, Hot Water, and Methanol Extracts, and Their Respective Ethyl Acetate Fractions, from Sanguisorba officinalis L. Roots. Molecules. 2018 Nov 16;23(11):3001. doi: 10.3390/molecules23113001. [PubMed:30453560 ]
Passari AK, Mishra VK, Singh G, Singh P, Kumar B, Gupta VK, Sarma RK, Saikia R, Donovan AO, Singh BP: Insights into the functionality of endophytic actinobacteria with a focus on their biosynthetic potential and secondary metabolites production. Sci Rep. 2017 Sep 18;7(1):11809. doi: 10.1038/s41598-017-12235-4. [PubMed:28924162 ]

Showing NP-Card for Arjunic acid (NP0141088)

MOL for NP0141088 (Arjunic acid)

3D MOL for NP0141088 (Arjunic acid)

3D SDF for NP0141088 (Arjunic acid)

3D-SDF for NP0141088 (Arjunic acid)

PDB for NP0141088 (Arjunic acid)

3D PDB for NP0141088 (Arjunic acid)

SMILES for NP0141088 (Arjunic acid)

INCHI for NP0141088 (Arjunic acid)

Structure for NP0141088 (Arjunic acid)

3D Structure for NP0141088 (Arjunic acid)