NP-MRD: Showing NP-Card for Carabrolate H (NP0333508)

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Record Information

Version

2.0

Created at

2024-06-25 12:12:24 UTC

Updated at

2024-09-03 04:22:44 UTC

NP-MRD ID

NP0333508

Natural Product DOI

https://doi.org/10.57994/2962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carabrolate H

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03092314472D          

 32 34  0  0  1  0            999 V2000
   -0.6928   -6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -5.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4073   -5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8362   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2651   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9796   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6941   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1230   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8375   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5520   -5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217   -6.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756   -5.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8631   -4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1487   -4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756   -6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5131   -4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9980   -5.3668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006   -3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6881   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527   -3.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -3.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201   -4.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -3.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -2.5648    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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 18 22  1  1  0  0  0
 18 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 21  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
 29 31  2  0  0  0  0
 28 32  2  0  0  0  0
M  END


  Mrv2104 03092314472D          

 32 34  0  0  1  0            999 V2000
   -0.6928   -6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -5.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4073   -5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8362   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2651   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9796   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6941   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4086   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1230   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8375   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5520   -5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217   -6.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7362   -5.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4506   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756   -5.4138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8631   -4.6993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1487   -4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756   -6.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006   -5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5131   -4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9980   -5.3668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006   -3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6881   -4.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527   -3.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -3.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201   -4.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -3.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -2.5648    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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 18 22  1  1  0  0  0
 18 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 21  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
 29 31  2  0  0  0  0
 28 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333508

> <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)CCCCCCCCO

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O5/c1-16(28-22(26)10-8-6-4-5-7-9-13-25)11-12-19-20-14-18-17(2)23(27)29-21(18)15-24(19,20)3/h16,18-21,25H,2,4-15H2,1,3H3/t16-,18-,19?,20+,21-,24-/m1/s1

> <INCHI_KEY>
PCDCQULQISVAFR-FKXKYRGJSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.563

> <EXACT_MASS>
406.271924324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.958106787993344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(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 9-hydroxynonanoate

> <JCHEM_LOGP>
4.613343506666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.84394282199191

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922497010525435

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
111.47949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(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 9-hydroxynonanoate

> <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      -1.293 -12.416   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.293 -10.876   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.627 -10.106   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.961 -10.876   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.294 -10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.628 -10.876   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.962 -10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.295 -10.876   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.629 -10.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.963 -10.876   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.296 -10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -14.630 -10.876   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -15.964 -10.106   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.961 -12.416   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.040 -10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.374 -10.876   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.708 -10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.248 -10.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.478  -8.772   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       2.144  -8.002   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       4.248  -7.438   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.248 -11.646   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.788 -10.106   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.558  -8.772   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       7.463 -10.018   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       5.788  -7.438   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       5.018  -8.772   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       6.818  -6.294   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.225  -6.920   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.064  -8.452   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.559  -6.150   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.498  -4.788   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
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                                                       
CONECT   13   12                                                            
CONECT   14    4                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   19   22   23                                             
CONECT   19   18   17   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   26                                                       
CONECT   22   18                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26   30                                             
CONECT   25   24                                                            
CONECT   26   24   21   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   24                                                       
CONECT   31   29                                                            
CONECT   32   28                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₈O₅

Average Mass

406.5630 Da

Monoisotopic Mass

406.27192 Da

IUPAC Name

(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 9-hydroxynonanoate

Traditional Name

(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 9-hydroxynonanoate

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)CCCCCCCCO

InChI Identifier

InChI=1S/C24H38O5/c1-16(28-22(26)10-8-6-4-5-7-9-13-25)11-12-19-20-14-18-17(2)23(27)29-21(18)15-24(19,20)3/h16,18-21,25H,2,4-15H2,1,3H3/t16-,18-,19?,20+,21-,24-/m1/s1

InChI Key

PCDCQULQISVAFR-FKXKYRGJSA-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

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	4.61	ChemAxon
pKa (Strongest Acidic)	16.84	ChemAxon
pKa (Strongest Basic)	-2	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	13	ChemAxon
Refractivity	111.48 m³·mol⁻¹	ChemAxon
Polarizability	46.96 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

Not Available

References

General References

Not Available

Showing NP-Card for Carabrolate H (NP0333508)

MOL for NP0333508 (Carabrolate H)

3D MOL for NP0333508 (Carabrolate H)

3D SDF for NP0333508 (Carabrolate H)

3D-SDF for NP0333508 (Carabrolate H)

PDB for NP0333508 (Carabrolate H)

3D PDB for NP0333508 (Carabrolate H)

SMILES for NP0333508 (Carabrolate H)

INCHI for NP0333508 (Carabrolate H)

Structure for NP0333508 (Carabrolate H)

3D Structure for NP0333508 (Carabrolate H)