NP-MRD: Showing NP-Card for Bulgarsenine (NP0140903)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-06-29 21:57:44 UTC

Updated at

2026-02-23 12:00:46 UTC

NP-MRD ID

NP0140903

Natural Product DOI

https://doi.org/10.57994/8054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bulgarsenine

Description

Bulgarsenine belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Bulgarsenine is found in Senecio nemorensis. Bulgarsenine was first documented in 1999 (PMID: 10425138). Based on a literature review very few articles have been published on Bulgarsenine (PMID: 41723793).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    2.3280   -3.2269   -0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -2.1450    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -2.2746    1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1657   -1.2460    2.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163   -1.0655    3.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401   -0.5265    1.6770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1082   -0.8135    1.2321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2365   -2.0359    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -1.5229   -0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3822   -0.1739   -0.9836 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1853    0.7646   -1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9611    2.0711   -0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3482    1.6147    0.4204 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9020    1.9601    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875    1.4955   -0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8823    1.5654   -1.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0151    1.7384   -2.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1188    1.4617   -0.5226 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3078    2.6940    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2459    1.3638   -1.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1307    0.1961    0.3450 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5850   -0.2726    0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4003   -0.8656   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    0.2206    0.3946 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8905   -3.8336    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998   -3.9050   -0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -2.7909   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -3.2444    2.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445   -1.0046    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462   -2.7932    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3068   -2.5212    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -1.5269   -0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4469   -2.1003   -1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    0.8738   -2.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2539    0.4864   -1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9234    2.5658   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    2.7375   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8771    2.2464    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242    1.7008    1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500    3.0899    0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040    3.5759   -0.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097    2.8791    0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    2.5601    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7864    2.1784   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7783    0.3965    1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6063   -1.3137    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    0.3392    1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1175   -0.0910   -0.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3203   -0.6928   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8127   -0.9334   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8434    0.1441    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 23  1  0
 23  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  6
 13 24  1  0
 18 21  1  0
 24  7  1  0
 24 10  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 21 45  1  1
 23 49  1  0
 23 50  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  7 29  1  1
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  1
 14 39  1  0
 14 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 24 51  1  6
M  END


  Mrv1652306292223572D          

 24 26  0  0  1  0            999 V2000
    7.9798   -0.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619   -1.0228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6770   -1.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9860   -2.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7163   -3.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9199   -3.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7079   -4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3354   -2.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389   -2.9795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0210   -3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2502   -3.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918   -2.5035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9544   -2.3973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1664   -1.5999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3590   -1.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8411   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9628   -1.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748   -0.5876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9713   -0.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1659    0.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6380   -0.9812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7278   -0.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1575   -0.3404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282   -1.7719    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
  4 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C\C(C)=C\C(=O)O[C@@H]2CCN3CC[C@H](COC(=O)[C@]1(C)O)[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO5/c1-11-8-12(2)18(3,22)17(21)23-10-13-4-6-19-7-5-14(16(13)19)24-15(20)9-11/h9,12-14,16,22H,4-8,10H2,1-3H3/b11-9+/t12-,13-,14-,16-,18-/m1/s1

> <INCHI_KEY>
KUYRTCOXLIWTED-SXBDOOTDSA-N

> <FORMULA>
C18H27NO5

> <MOLECULAR_WEIGHT>
337.416

> <EXACT_MASS>
337.188922973

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      14.896  -0.711   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.929  -1.909   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.330  -3.396   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.040  -4.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.537  -5.846   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.050  -6.247   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.655  -7.735   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.959  -5.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.473  -5.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.506  -6.760   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.067  -6.211   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.145  -4.673   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.382  -4.475   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.777  -2.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.270  -2.185   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.303  -3.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.264  -2.585   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.660  -1.097   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.146  -0.695   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.510   0.801   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.391  -1.832   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.559  -0.301   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.361  -0.635   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.813  -3.308   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    4                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₇NO₅

Average Mass

337.4160 Da

Monoisotopic Mass

337.18892 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1C\C(C)=C\C(=O)O[C@@H]2CCN3CC[C@H](COC(=O)[C@]1(C)O)[C@H]23

InChI Identifier

InChI=1S/C18H27NO5/c1-11-8-12(2)18(3,22)17(21)23-10-13-4-6-19-7-5-14(16(13)19)24-15(20)9-11/h9,12-14,16,22H,4-8,10H2,1-3H3/b11-9+/t12-,13-,14-,16-,18-/m1/s1

InChI Key

KUYRTCOXLIWTED-SXBDOOTDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 90.9, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.63, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-23	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Senecio doronicum		Not Available
Senecio nemorensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Pyrrolizidine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Amine
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Organopnictogen compound
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

Not Available

Chemspider ID

4947253

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

P rez-Castorena AL, Arciniegas A, P rez R, Gutierrez H, Toscano RA, Villasenor JL, Romo de Vivar A: Iodanthine, a pyrrolizidine alkaloid from senecio iodanthus and senecio bracteatus. J Nat Prod. 1999 Jul;62(7):1039-43. doi: 10.1021/np980562k. [PubMed:10425138 ]
Barthlott W: The purity of sacred lotus: superhydrophobic self-cleaning plant surfaces and the consequences revisited. Planta. 2026 Feb 22;263(3):80. doi: 10.1007/s00425-026-04937-9. [PubMed:41723793 ]
DOI: 10.1016/0031-9422(80)83116-5

Showing NP-Card for Bulgarsenine (NP0140903)

MOL for NP0140903 (Bulgarsenine)

3D MOL for NP0140903 (Bulgarsenine)

3D SDF for NP0140903 (Bulgarsenine)

3D-SDF for NP0140903 (Bulgarsenine)

PDB for NP0140903 (Bulgarsenine)

3D PDB for NP0140903 (Bulgarsenine)

SMILES for NP0140903 (Bulgarsenine)

INCHI for NP0140903 (Bulgarsenine)

Structure for NP0140903 (Bulgarsenine)

3D Structure for NP0140903 (Bulgarsenine)