NP-MRD: Showing NP-Card for Andrograpanin (NP0141232)

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Record Information

Version

1.0

Created at

2022-06-29 22:18:55 UTC

Updated at

2022-06-29 22:18:55 UTC

NP-MRD ID

NP0141232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Andrograpanin

Description

Andrograpanin belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Andrograpanin is found in Andrographis affinis, Andrographis paniculata and Potamogeton natans. It was first documented in 2020 (PMID: 34803268). Based on a literature review a significant number of articles have been published on andrograpanin (PMID: 34997448) (PMID: 35250036) (PMID: 35066371) (PMID: 34393414).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    1.3482   -3.0550   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720   -2.1735    0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910   -2.6435   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092   -1.7225    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7654   -0.3495    0.5111 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4223    0.1075   -0.0313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4143   -0.2006   -1.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    1.5617    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997    2.3129    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155    1.9826   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8977    0.5827    0.3297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6344    0.7405    1.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9760    0.1232   -0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9465    1.1559   -0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -0.7985    0.6138 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9809   -0.3913    0.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6615   -0.1633   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0638    0.2344   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6311    1.3602   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400    1.3987   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478    0.1803    0.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0567   -0.5495    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245   -1.7093    0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056   -4.0378   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3949   -2.8908    0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9390   -2.8857   -1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825   -3.6678    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7469   -2.1902    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7738   -1.6742   -0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5772   -0.4708    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3749   -0.5949   -1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -0.9363   -1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    0.7624   -2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    1.8219    0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0295    2.0865   -0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1038    3.3925    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4187    1.9610    1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2374    2.0339   -1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3386    2.6891    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315    1.6692    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9415    0.7848    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3693   -0.0873    1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046   -0.7775   -0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6660    0.0282   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6209    1.0255    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2601   -0.8621    1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5775   -1.1754    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860    0.5093    1.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7157   -1.0664   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.5922   -1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    2.1988   -1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1416    2.2044    0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7451    1.5733   -1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  6
  6 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 15  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 11  1  0
  5  6  1  0
 22 18  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 10 38  1  0
 10 39  1  0
  9 36  1  0
  9 37  1  0
  8 34  1  0
  8 35  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 15 46  1  1
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  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  1
M  END


  Mrv1652306302200182D          

 23 25  0  0  1  0            999 V2000
    0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  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
   -0.7145   -1.2375    0.0000 C   0  0  0  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  2  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  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -4.9820    0.0000 O   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
    0.6914   -3.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    0.4887    0.0000 O   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  1  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
  6 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  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  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
  6 21  1  1  0  0  0
  2 22  1  1  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CO)CCC[C@@]2(C)[C@H](CCC3=CCOC3=O)C(=C)CC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-14-5-8-17-19(2,13-21)10-4-11-20(17,3)16(14)7-6-15-9-12-23-18(15)22/h9,16-17,21H,1,4-8,10-13H2,2-3H3/t16-,17-,19+,20+/m1/s1

> <INCHI_KEY>
WKKBRRFSRMDTJB-JYBIWHBTSA-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       0.990   1.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   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  C   UNK     0       4.771  -9.300   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.231  -9.300   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.755  -7.835   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.291  -7.359   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.506   0.912   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   21                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   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   20                                                  
CONECT   20   19                                                            
CONECT   21    6                                                            
CONECT   22    2   23                                                       
CONECT   23   22                                                            
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

C[C@@]1(CO)CCC[C@@]2(C)[C@H](CCC3=CCOC3=O)C(=C)CC[C@H]12

InChI Identifier

InChI=1S/C20H30O3/c1-14-5-8-17-19(2,13-21)10-4-11-20(17,3)16(14)7-6-15-9-12-23-18(15)22/h9,16-17,21H,1,4-8,10-13H2,2-3H3/t16-,17-,19+,20+/m1/s1

InChI Key

WKKBRRFSRMDTJB-JYBIWHBTSA-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
Andrographis affinis	LOTUS Database	35616633
Andrographis paniculata	LOTUS Database	35616633
Potamogeton natans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Primary alcohol
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

C00022415

Chemspider ID

9841603

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11666871

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shivashankar S, Sangeetha MK: The Natural Ligand for Metalloproteinase-A Multifaceted Drug Target. Appl Biochem Biotechnol. 2022 Apr;194(4):1716-1739. doi: 10.1007/s12010-021-03778-4. Epub 2022 Jan 8. [PubMed:34997448 ]
Majumdar M, Singh V, Misra TK, Roy DN: In silico studies on structural inhibition of SARS-CoV-2 main protease M(pro) by major secondary metabolites of Andrographis paniculata and Cinchona officinalis. Biologia (Bratisl). 2022;77(5):1373-1389. doi: 10.1007/s11756-022-01012-y. Epub 2022 Feb 28. [PubMed:35250036 ]
Yin B, Umar T, Ma X, Chen Y, Umar Z, Umer S, Deng G: Andrograpanin mitigates lipopolysaccharides induced endometritis via TLR4/NF-kappaB pathway. Reprod Biol. 2022 Mar;22(1):100606. doi: 10.1016/j.repbio.2022.100606. Epub 2022 Jan 20. [PubMed:35066371 ]
Deiva Suga SS, Krishna Mohan S, Sreekandan RN, K M, Kamaraj D, Veeraraghavan VP, Jayaraman S, Rajagopal P: Molecular docking analysis of phytocompounds from Andrographis paniculata binding with proteins in the notch-signaling pathway. Bioinformation. 2020 Nov 30;16(11):923-928. doi: 10.6026/97320630016923. eCollection 2020. [PubMed:34803268 ]
Roy A: Molecular docking analysis of compounds from Andrographis paniculata with EGFR. Bioinformation. 2021 Jan 31;17(1):23-28. doi: 10.6026/97320630017023. eCollection 2021. [PubMed:34393414 ]

Showing NP-Card for Andrograpanin (NP0141232)

MOL for NP0141232 (Andrograpanin)

3D MOL for NP0141232 (Andrograpanin)

3D SDF for NP0141232 (Andrograpanin)

3D-SDF for NP0141232 (Andrograpanin)

PDB for NP0141232 (Andrograpanin)

3D PDB for NP0141232 (Andrograpanin)

SMILES for NP0141232 (Andrograpanin)

INCHI for NP0141232 (Andrograpanin)

Structure for NP0141232 (Andrograpanin)

3D Structure for NP0141232 (Andrograpanin)