NP-MRD: Showing NP-Card for (+)-makassaric acid (NP0027626)

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Record Information

Version

2.0

Created at

2021-06-19 19:43:58 UTC

Updated at

2021-06-29 23:53:51 UTC

NP-MRD ID

NP0027626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-makassaric acid

Provided By

JEOL Database JEOL Logo

Description

(+)-makassaric acid is found in Acanthodendrilla sp. (+)-makassaric acid was first documented in 2004 (Williams, D. E., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121433D          

 68 71  0  0  0  0            999 V2000
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    1.4447   -2.3348   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192121433D          

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    2.6688   -0.7799    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6855   -1.9497    1.4592 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4409    1.4664   -2.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
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 26 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C(=C(O[H])C([H])=C1[H])C([H])([H])[C@@]1([H])C(=C([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O3/c1-17-7-10-23-26(4,14-11-22-25(2,3)12-6-13-27(22,23)5)20(17)16-19-15-18(24(29)30)8-9-21(19)28/h7-9,15,20,22-23,28H,6,10-14,16H2,1-5H3,(H,29,30)/t20-,22-,23-,26-,27-/m0/s1

> <INCHI_KEY>
VIOMEESUKISOEL-RMRWLJQJSA-N

> <FORMULA>
C27H38O3

> <MOLECULAR_WEIGHT>
410.598

> <EXACT_MASS>
410.282095084

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.47414462248404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(1S,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
6.66

> <JCHEM_LOGP>
6.954320621666668

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.916865618194882

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.375698126309246

> <JCHEM_PKA_STRONGEST_BASIC>
-6.062708426605323

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
122.45419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.83e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1S,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthren-1-yl]methyl}-4-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    2.3229   -3.3724   -0.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4409    1.4664   -2.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 31  1  0
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  1 33  1  0
 30 68  1  0
 26 65  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       2.323  -3.372  -0.900  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.445  -2.335  -0.259  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.439  -2.680   0.566  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.546  -1.713   1.161  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.331  -0.222   0.781  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.580   0.717   1.064  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.816   0.300   0.226  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.957   0.600   2.570  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.938   1.666   3.055  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.443   3.075   2.762  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.086   3.327   1.275  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.369   3.470   0.435  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.371   4.702   1.219  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.115   2.196   0.783  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.620   2.358  -0.669  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.574   1.441  -0.956  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.337  -0.059  -0.627  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.535  -0.635  -1.783  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.708  -0.870  -0.616  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.792  -0.321   0.366  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.221  -0.523  -0.099  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.066  -1.403   0.597  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.393  -1.598   0.189  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.233  -2.550   0.957  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.879  -3.196   1.926  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.484  -2.649   0.473  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.887  -0.900  -0.919  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.061  -0.011  -1.611  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.742   0.174  -1.196  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.937   1.058  -1.856  0.00  0.00           O+0
HETATM   31  H   UNK     0       1.971  -4.389  -0.693  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.328  -3.246  -1.987  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.349  -3.303  -0.536  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.271  -3.729   0.803  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.539  -2.060   0.868  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.498  -1.814   2.253  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.431   0.128   1.496  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.841  -0.769   0.010  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.759   0.502   0.740  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.878   0.817  -0.733  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.387  -0.388   2.779  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.048   0.676   3.182  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.930   1.516   2.617  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.072   1.555   4.138  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.199   3.797   3.099  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.554   3.256   3.382  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.942   4.350   0.752  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.142   3.602  -0.628  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.043   2.619   0.534  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.396   4.666   1.718  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.212   5.041   0.190  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.966   5.476   1.719  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.215   2.334   1.406  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.418   2.184  -1.395  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.281   3.384  -0.846  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.867   1.551  -2.009  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.407   1.849  -0.381  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.934  -1.629  -1.568  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.055  -0.716  -2.705  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.383   0.005  -2.030  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.096  -0.834  -1.643  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.688   0.748   0.559  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.669  -0.780   1.357  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.686  -1.950   1.459  0.00  0.00           H+0
HETATM   65  H   UNK     0       8.911  -3.299   1.069  0.00  0.00           H+0
HETATM   66  H   UNK     0       7.913  -1.038  -1.250  0.00  0.00           H+0
HETATM   67  H   UNK     0       6.463   0.527  -2.463  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.441   1.466  -2.579  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2   19    3    1                                                  
CONECT    3    2    4   34                                                  
CONECT    4    5    3   35   36                                             
CONECT    5   37   17    4    6                                             
CONECT    6    8   14    7    5                                             
CONECT    7    6   38   39   40                                             
CONECT    8    6    9   41   42                                             
CONECT    9   10    8   43   44                                             
CONECT   10    9   11   45   46                                             
CONECT   11   14   10   12   13                                             
CONECT   12   11   47   48   49                                             
CONECT   13   11   50   51   52                                             
CONECT   14   11    6   53   15                                             
CONECT   15   16   14   54   55                                             
CONECT   16   15   17   56   57                                             
CONECT   17   16    5   18   19                                             
CONECT   18   17   58   59   60                                             
CONECT   19    2   17   20   61                                             
CONECT   20   19   21   62   63                                             
CONECT   21   29   20   22                                                  
CONECT   22   23   21   64                                                  
CONECT   23   27   22   24                                                  
CONECT   24   23   26   25                                                  
CONECT   25   24                                                            
CONECT   26   24   65                                                       
CONECT   27   28   23   66                                                  
CONECT   28   29   27   67                                                  
CONECT   29   21   28   30                                                  
CONECT   30   29   68                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    9                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   16                                                            
CONECT   58   18                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   19                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   22                                                            
CONECT   65   26                                                            
CONECT   66   27                                                            
CONECT   67   28                                                            
CONECT   68   30                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

RDKit          3D

68 71  0  0  0  0  0  0  0  0999 V2000
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 30 68  1  0
 26 65  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₃

Average Mass

410.5980 Da

Monoisotopic Mass

410.28210 Da

IUPAC Name

3-{[(1S,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}-4-hydroxybenzoic acid

Traditional Name

3-{[(1S,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthren-1-yl]methyl}-4-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C(=C(O[H])C([H])=C1[H])C([H])([H])[C@@]1([H])C(=C([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H38O3/c1-17-7-10-23-26(4,14-11-22-25(2,3)12-6-13-27(22,23)5)20(17)16-19-15-18(24(29)30)8-9-21(19)28/h7-9,15,20,22-23,28H,6,10-14,16H2,1-5H3,(H,29,30)/t20-,22-,23-,26-,27-/m0/s1

InChI Key

VIOMEESUKISOEL-RMRWLJQJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthodendrilla sp.	JEOL database	Williams, D. E., et al, J. Nat. Prod. 67, 2127 (2004)

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	6.66	ALOGPS
logP	6.95	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	122.45 m³·mol⁻¹	ChemAxon
Polarizability	48.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Williams, D. E., et al. (2004). Williams, D. E., et al, J. Nat. Prod. 67, 2127 (2004). J. Nat. Prod..

Showing NP-Card for (+)-makassaric acid (NP0027626)

MOL for NP0027626 ((+)-makassaric acid)

3D MOL for NP0027626 ((+)-makassaric acid)

3D SDF for NP0027626 ((+)-makassaric acid)

3D-SDF for NP0027626 ((+)-makassaric acid)

PDB for NP0027626 ((+)-makassaric acid)

3D PDB for NP0027626 ((+)-makassaric acid)

SMILES for NP0027626 ((+)-makassaric acid)

INCHI for NP0027626 ((+)-makassaric acid)

Structure for NP0027626 ((+)-makassaric acid)

3D Structure for NP0027626 ((+)-makassaric acid)