NP-MRD: Showing NP-Card for Caulophylline A (NP0353553)

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Record Information

Version

2.0

Created at

2026-02-23 20:06:18 UTC

Updated at

2026-02-24 00:01:39 UTC

NP-MRD ID

NP0353553

Natural Product DOI

https://doi.org/10.57994/8091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caulophylline A

Description

Caulophylline A was first documented in 2011 (PMID: 21596111).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03242317182D          

 26 28  0  0  0  0            999 V2000
    1.9339    2.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573    2.9379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    3.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053    3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
  3 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
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 13 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END


  Mrv2104 03242317182D          

 26 28  0  0  0  0            999 V2000
    1.9339    2.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645   -0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573    2.9379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    3.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053    3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
  3 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
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 13 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0353553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=O)C3=C(C2=C1OC)C(O)=C(OC)C=C3CCN(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO5/c1-21(2)9-8-11-10-14(25-4)19(23)17-15(11)18(22)12-6-7-13(24-3)20(26-5)16(12)17/h6-7,10,23H,8-9H2,1-5H3

> <INCHI_KEY>
YCJMMOZHYTZHHN-UHFFFAOYSA-N

> <FORMULA>
C20H23NO5

> <MOLECULAR_WEIGHT>
357.406

> <EXACT_MASS>
357.157622845

$$$$

HEADER    PROTEIN                                 24-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAR-23         0                                  
HETATM    1  O   UNK     0       3.610   4.360   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.610   2.820   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.947  -1.519   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.454  -1.199   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.410  -0.695   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.935  -2.159   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.428  -2.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.285  -2.159   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.727  -1.519   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.234  -1.199   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.382   3.699   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.124   4.019   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -1.600   5.484   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -3.107   5.804   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.570   6.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    3   13                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20    2   13                                                  
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₅

Average Mass

357.4060 Da

Monoisotopic Mass

357.15762 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=O)C3=C(C2=C1OC)C(O)=C(OC)C=C3CCN(C)C

InChI Identifier

InChI=1S/C20H23NO5/c1-21(2)9-8-11-10-14(25-4)19(23)17-15(11)18(22)12-6-7-13(24-3)20(26-5)16(12)17/h6-7,10,23H,8-9H2,1-5H3

InChI Key

YCJMMOZHYTZHHN-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-23	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Caulophyllum robustum Maxim.		Not Available

Chemical Taxonomy

Classification

Not classified

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

Not Available

References

General References

Showing NP-Card for Caulophylline A (NP0353553)

MOL for NP0353553 (Caulophylline A)

3D MOL for NP0353553 (Caulophylline A)

3D SDF for NP0353553 (Caulophylline A)

3D-SDF for NP0353553 (Caulophylline A)

PDB for NP0353553 (Caulophylline A)

3D PDB for NP0353553 (Caulophylline A)

SMILES for NP0353553 (Caulophylline A)

INCHI for NP0353553 (Caulophylline A)

Structure for NP0353553 (Caulophylline A)

3D Structure for NP0353553 (Caulophylline A)