NP-MRD: Showing NP-Card for Carabrolate D (NP0333304)

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Record Information

Version

2.0

Created at

2024-05-27 09:01:24 UTC

Updated at

2024-09-03 04:21:54 UTC

NP-MRD ID

NP0333304

Natural Product DOI

https://doi.org/10.57994/2661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carabrolate D

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02082311372D          

 32 35  0  0  1  0            999 V2000
   -3.4826    3.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695    3.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557    4.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020    5.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    5.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    3.7934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5474    3.1260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    4.5079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2375    3.7934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.7934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.0789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.6664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    3.0789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8250    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    3.0789    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  1  0  0  0  0
  3  5  2  0  0  0  0
  6  2  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  4  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 17 27  2  0  0  0  0
 15 28  1  6  0  0  0
 11 29  1  1  0  0  0
 11 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  6 32  1  0  0  0  0
M  END


  Mrv2104 02082311372D          

 32 35  0  0  1  0            999 V2000
   -3.4826    3.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695    3.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557    4.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020    5.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    5.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    3.7934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5474    3.1260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    4.5079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2375    3.7934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.7934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.0789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.6664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    3.0789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8250    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    3.0789    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  1  0  0  0  0
  3  5  2  0  0  0  0
  6  2  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  4  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 17 27  2  0  0  0  0
 15 28  1  6  0  0  0
 11 29  1  1  0  0  0
 11 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  6 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]3([H])C(=C)C(=O)O[C@]3([H])C[C@]1(C)[C@H]2CC[C@@H](C)OC(=O)CC1=C(C)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O5/c1-13-9-17(25)7-6-16(13)10-22(26)28-14(2)5-8-19-20-11-18-15(3)23(27)29-21(18)12-24(19,20)4/h6-7,9,14,18-21,25H,3,5,8,10-12H2,1-2,4H3/t14-,18-,19+,20+,21-,24-/m1/s1

> <INCHI_KEY>
XOAOJZFILQBSDI-VINORDOSSA-N

> <FORMULA>
C24H30O5

> <MOLECULAR_WEIGHT>
398.499

> <EXACT_MASS>
398.209324066

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.33585900588116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.726270173666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.619186294031834

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958823381522777

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
109.06190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-FEB-23         0                                  
HETATM    1  C   UNK     0      -6.501   6.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.356   7.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.517   8.933   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.110   9.559   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -6.851   9.703   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.850   7.081   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      -4.755   5.835   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      -3.080   8.415   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -2.310   7.081   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0      -1.540   8.415   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770   7.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   5.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   4.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   5.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   4.977   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   5.747   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668   4.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   5.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   4.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   5.747   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   7.287   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003   4.977   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003   3.437   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.337   2.667   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669   2.667   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   3.437   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668   3.437   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001   3.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.564   7.851   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.540   5.747   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      -1.540   4.207   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      -3.080   5.747   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    8                                                       
CONECT    5    3                                                            
CONECT    6    2    7    8   32                                             
CONECT    7    6                                                            
CONECT    8    6    4    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   29   30                                             
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19                                                       
CONECT   27   17                                                            
CONECT   28   15                                                            
CONECT   29   11                                                            
CONECT   30   11   12   31   32                                             
CONECT   31   30                                                            
CONECT   32   30    6                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Carabrolic acid D	Generator

Chemical Formula

C₂₄H₃₀O₅

Average Mass

398.4990 Da

Monoisotopic Mass

398.20932 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]3([H])C(=C)C(=O)O[C@]3([H])C[C@]1(C)[C@H]2CC[C@@H](C)OC(=O)CC1=C(C)C=C(O)C=C1

InChI Identifier

InChI=1S/C24H30O5/c1-13-9-17(25)7-6-16(13)10-22(26)28-14(2)5-8-19-20-11-18-15(3)23(27)29-21(18)12-24(19,20)4/h6-7,9,14,18-21,25H,3,5,8,10-12H2,1-2,4H3/t14-,18-,19+,20+,21-,24-/m1/s1

InChI Key

XOAOJZFILQBSDI-VINORDOSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	Not Available	Lu Fu	2024-05-27	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	Not Available	Lu Fu	2024-05-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	Not Available	Lu Fu	2024-05-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	Not Available	Lu Fu	2024-05-27	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	lufu_kclz110@126.com	Not Available	Lu Fu	2024-05-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	lufu_kclz110@126.com	Not Available	Lu Fu	2024-05-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	lufu_kclz110@126.com	Not Available	Lu Fu	2024-05-27	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
Fatty alcohol ester
M-cresol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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)	9.62	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.06 m³·mol⁻¹	ChemAxon
Polarizability	42.34 Å³	ChemAxon
Number of Rings	4	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 D (NP0333304)

MOL for NP0333304 (Carabrolate D)

3D MOL for NP0333304 (Carabrolate D)

3D SDF for NP0333304 (Carabrolate D)

3D-SDF for NP0333304 (Carabrolate D)

PDB for NP0333304 (Carabrolate D)

3D PDB for NP0333304 (Carabrolate D)

SMILES for NP0333304 (Carabrolate D)

INCHI for NP0333304 (Carabrolate D)

Structure for NP0333304 (Carabrolate D)

3D Structure for NP0333304 (Carabrolate D)