NP-MRD: Showing NP-Card for Carabrolate J (NP0333510)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-06-25 12:28:15 UTC

Updated at

2024-09-03 04:22:44 UTC

NP-MRD ID

NP0333510

Natural Product DOI

https://doi.org/10.57994/2964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carabrolate J

Description

Carabrolate J is also known as carabrolic acid J. Based on a literature review very few articles have been published on Carabrolate J.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03092315032D          

 33 35  0  0  1  0            999 V2000
    0.3020   -1.9520    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
   -0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4205   -1.0799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751    0.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7425   -0.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432    0.9920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035    1.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    1.4289    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9849   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1296   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -2.3645    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
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  2  0  0  0  0
  8 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 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
 25 26  1  0  0  0  0
 26 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
 29 31  2  0  0  0  0
 21 32  2  0  0  0  0
 19 33  1  6  0  0  0
M  END


  Mrv2104 03092315032D          

 33 35  0  0  1  0            999 V2000
    0.3020   -1.9520    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
   -0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4205   -1.0799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751    0.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8287    0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7425   -0.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5432    0.9920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035    1.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    1.4289    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9849   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1296   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -2.3645    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
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  2  0  0  0  0
  8 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 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
 25 26  1  0  0  0  0
 26 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
 29 31  2  0  0  0  0
 21 32  2  0  0  0  0
 19 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0333510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]3([H])C(=C)C(=O)O[C@]3([H])C[C@]1(C)C2CC[C@@H](C)OC(=O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O6/c1-15(29-22(27)10-8-6-4-5-7-9-21(25)26)11-12-18-19-13-17-16(2)23(28)30-20(17)14-24(18,19)3/h15,17-20H,2,4-14H2,1,3H3,(H,25,26)/t15-,17-,18?,19+,20-,24-/m1/s1

> <INCHI_KEY>
UFFPXKADNLELRM-ITGBXOGYSA-N

> <FORMULA>
C24H36O6

> <MOLECULAR_WEIGHT>
420.546

> <EXACT_MASS>
420.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.148828721349986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-{[(2R)-4-[(1R,3S,5R,7R)-5-methyl-10-methylidene-9-oxo-8-oxatricyclo[5.3.0.0^{3,5}]decan-4-yl]butan-2-yl]oxy}-9-oxononanoic acid

> <JCHEM_LOGP>
4.729780358333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.448840510551538

> <JCHEM_PKA_STRONGEST_BASIC>
-6.642881891781947

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
111.21619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-{[(2R)-4-[(1R,3S,5R,7R)-5-methyl-10-methylidene-9-oxo-8-oxatricyclo[5.3.0.0^{3,5}]decan-4-yl]butan-2-yl]oxy}-9-oxononanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAR-23         0                                  
HETATM    1  C   UNK     0       0.564  -3.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.746  -0.770   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0      -2.652  -2.016   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0      -0.976   0.564   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      -0.206  -0.770   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      -2.007   1.708   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.414   1.082   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.253  -0.450   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.747   1.852   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.687   3.214   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564   0.564   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       2.667   0.000   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       2.104  -2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.771  -2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.438  -2.104   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.772  -2.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.106  -2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.439  -2.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.773  -2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.107  -2.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.440  -2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.774  -2.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.108  -2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.442  -2.874   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      20.775  -2.104   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      19.442  -4.414   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.772  -4.414   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.105  -4.414   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6   10                                             
CONECT    5    4                                                            
CONECT    6    4    7    8   14                                             
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    2   14   15   16                                             
CONECT   14   13    6                                                       
CONECT   15   13                                                            
CONECT   16   13    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   21                                                            
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Carabrolic acid J	Generator

Chemical Formula

C₂₄H₃₆O₆

Average Mass

420.5460 Da

Monoisotopic Mass

420.25119 Da

IUPAC Name

9-{[(2R)-4-[(1R,3S,5R,7R)-5-methyl-10-methylidene-9-oxo-8-oxatricyclo[5.3.0.0^{3,5}]decan-4-yl]butan-2-yl]oxy}-9-oxononanoic acid

Traditional Name

9-{[(2R)-4-[(1R,3S,5R,7R)-5-methyl-10-methylidene-9-oxo-8-oxatricyclo[5.3.0.0^{3,5}]decan-4-yl]butan-2-yl]oxy}-9-oxononanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]3([H])C(=C)C(=O)O[C@]3([H])C[C@]1(C)C2CC[C@@H](C)OC(=O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C24H36O6/c1-15(29-22(27)10-8-6-4-5-7-9-21(25)26)11-12-18-19-13-17-16(2)23(28)30-20(17)14-24(18,19)3/h15,17-20H,2,4-14H2,1,3H3,(H,25,26)/t15-,17-,18?,19+,20-,24-/m1/s1

InChI Key

UFFPXKADNLELRM-ITGBXOGYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	20081993fulu	Lu Fu	2024-06-25	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	20081993fulu	Lu Fu	2024-06-25	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	20081993fulu	Lu Fu	2024-06-25	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	20081993fulu	Lu Fu	2024-06-25	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	lufu_kclz110@126.com	20081993fulu	Lu Fu	2024-06-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	lufu_kclz110@126.com	20081993fulu	Lu Fu	2024-06-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	20081993fulu	Lu Fu	2024-06-25	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Carpesium. abrotanoides		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Xanthanolides

Alternative Parents

Substituents

Xanthanolide-skeleton
Carabrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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
logP	4.73	ChemAxon
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	111.22 m³·mol⁻¹	ChemAxon
Polarizability	47.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Carabrolate J (NP0333510)

MOL for NP0333510 (Carabrolate J)

3D MOL for NP0333510 (Carabrolate J)

3D SDF for NP0333510 (Carabrolate J)

3D-SDF for NP0333510 (Carabrolate J)

PDB for NP0333510 (Carabrolate J)

3D PDB for NP0333510 (Carabrolate J)

SMILES for NP0333510 (Carabrolate J)

INCHI for NP0333510 (Carabrolate J)

Structure for NP0333510 (Carabrolate J)

3D Structure for NP0333510 (Carabrolate J)