NP-MRD: Showing NP-Card for Carabrolate B (NP0333302)

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Record Information

Version

2.0

Created at

2024-05-27 08:52:18 UTC

Updated at

2024-09-03 04:21:54 UTC

NP-MRD ID

NP0333302

Natural Product DOI

https://doi.org/10.57994/2659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carabrolate B

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02082311282D          

 37 40  0  0  1  0            999 V2000
   -0.8842   -5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8842   -5.1118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5987   -4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1711   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6000   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3145   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0289   -5.1118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1152   -5.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9221   -6.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3346   -5.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7826   -4.7763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.9541   -3.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2577   -6.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1698   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2592   -4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0842   -4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6717   -3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9572   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8066   -4.6523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4967   -3.9849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612   -2.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2149   -2.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1287   -3.8133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9294   -2.5803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897   -1.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 14 18  2  0  0  0  0
  4 19  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 23 27  1  1  0  0  0
 23 28  1  0  0  0  0
 29 28  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 26  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 34 36  2  0  0  0  0
 33 37  2  0  0  0  0
M  END


  Mrv2104 02082311282D          

 37 40  0  0  1  0            999 V2000
   -0.8842   -5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8842   -5.1118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5987   -4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1711   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6000   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3145   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0289   -5.1118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1152   -5.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9221   -6.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3346   -5.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7826   -4.7763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.9541   -3.9693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2577   -6.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1698   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2592   -4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0842   -4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6717   -3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9572   -3.5724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217   -3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8066   -4.6523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4967   -3.9849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612   -2.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2149   -2.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1287   -3.8133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9294   -2.5803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897   -1.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 14 18  2  0  0  0  0
  4 19  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 23 27  1  1  0  0  0
 23 28  1  0  0  0  0
 29 28  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 26  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 34 36  2  0  0  0  0
 33 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333302

> <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)CCCCCCC[C@@H]1OC(=O)C[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O7/c1-16(11-12-19-20-13-18-17(2)26(31)34-23(18)15-27(19,20)3)32-24(29)10-8-6-4-5-7-9-22-21(28)14-25(30)33-22/h16,18-23,28H,2,4-15H2,1,3H3/t16-,18-,19+,20+,21-,22+,23-,27-/m1/s1

> <INCHI_KEY>
KRRGPZSMGZTOKC-OCUFPGIESA-N

> <FORMULA>
C27H40O7

> <MOLECULAR_WEIGHT>
476.61

> <EXACT_MASS>
476.277403628

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.906498749593595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <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 8-[(2S,3R)-3-hydroxy-5-oxooxolan-2-yl]octanoate

> <JCHEM_LOGP>
4.422242803999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.911102713266903

> <JCHEM_PKA_STRONGEST_BASIC>
-3.275083673217057

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
124.40399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <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 8-[(2S,3R)-3-hydroxy-5-oxooxolan-2-yl]octanoate

> <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      -1.651 -11.082   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.651  -9.542   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.984  -8.772   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.318  -9.542   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.652  -8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.985  -9.542   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.319  -8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.653  -9.542   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.986  -8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.320  -9.542   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.654  -8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -14.987  -9.542   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -15.148 -11.074   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -16.655 -11.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -17.425 -10.060   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -16.394  -8.916   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -16.714  -7.409   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -17.281 -12.801   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.318 -11.082   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.317  -8.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.017  -9.542   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.350  -8.772   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.890  -8.772   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.120  -7.438   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.787  -6.668   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       3.890  -6.105   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.890 -10.312   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.430  -8.772   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.200  -7.438   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       7.106  -8.684   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       5.430  -6.105   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       4.660  -7.438   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       6.461  -4.960   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.868  -5.587   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.707  -7.118   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.201  -4.817   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.141  -3.454   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16                                                            
CONECT   18   14                                                            
CONECT   19    4                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   24   27   28                                             
CONECT   24   23   22   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   31                                                       
CONECT   27   23                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30   31   35                                             
CONECT   30   29                                                            
CONECT   31   29   26   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   29                                                       
CONECT   36   34                                                            
CONECT   37   33                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₇

Average Mass

476.6100 Da

Monoisotopic Mass

476.27740 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 8-[(2S,3R)-3-hydroxy-5-oxooxolan-2-yl]octanoate

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 8-[(2S,3R)-3-hydroxy-5-oxooxolan-2-yl]octanoate

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)CCCCCCC[C@@H]1OC(=O)C[C@H]1O

InChI Identifier

InChI=1S/C27H40O7/c1-16(11-12-19-20-13-18-17(2)26(31)34-23(18)15-27(19,20)3)32-24(29)10-8-6-4-5-7-9-22-21(28)14-25(30)33-22/h16,18-23,28H,2,4-15H2,1,3H3/t16-,18-,19+,20+,21-,22+,23-,27-/m1/s1

InChI Key

KRRGPZSMGZTOKC-OCUFPGIESA-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	Not Available	Lu Fu	2024-05-27	View Spectrum
HMBC NMR	[¹H, ¹³C] 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

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
logP	4.42	ChemAxon
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	124.4 m³·mol⁻¹	ChemAxon
Polarizability	52.91 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Carabrolate B (NP0333302)

MOL for NP0333302 (Carabrolate B)

3D MOL for NP0333302 (Carabrolate B)

3D SDF for NP0333302 (Carabrolate B)

3D-SDF for NP0333302 (Carabrolate B)

PDB for NP0333302 (Carabrolate B)

3D PDB for NP0333302 (Carabrolate B)

SMILES for NP0333302 (Carabrolate B)

INCHI for NP0333302 (Carabrolate B)

Structure for NP0333302 (Carabrolate B)

3D Structure for NP0333302 (Carabrolate B)