NP-MRD: Showing NP-Card for Brunnesin (NP0333051)

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Record Information

Version

1.0

Created at

2024-05-04 03:43:46 UTC

Updated at

2024-05-06 00:10:52 UTC

NP-MRD ID

NP0333051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brunnesin

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01162306202D          

 36 39  0  0  1  0            999 V2000
    6.3109    0.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932    1.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4530    0.2175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0283   -0.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6364    0.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5037    0.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807    1.1833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9755    0.5354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3312    2.0274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3216    1.2261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6032    1.6317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2151    0.9047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3472    0.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633    1.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3031    0.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9772    2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367    1.8819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794    2.5378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8381    3.3506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3937    2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1597    2.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2776    1.6192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0501    1.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182    2.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336    1.4378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089    0.8465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9270    0.5833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6083    0.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888   -1.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306   -0.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1900    0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    2.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 16  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
  9 25  1  6  0  0  0
 25 26  1  0  0  0  0
 27 26  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 25 36  2  0  0  0  0
M  END


  Mrv2104 01162306202D          

 36 39  0  0  1  0            999 V2000
    6.3109    0.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932    1.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4530    0.2175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0283   -0.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6364    0.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5037    0.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6807    1.1833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9755    0.5354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3312    2.0274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3216    1.2261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6032    1.6317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2151    0.9047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3472    0.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8633    1.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3031    0.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9772    2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367    1.8819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794    2.5378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8381    3.3506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3937    2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1597    2.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2776    1.6192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0501    1.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182    2.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336    1.4378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089    0.8465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9270    0.5833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6083    0.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8489   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483   -1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888   -1.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306   -0.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1900    0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    2.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 16  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
  9 25  1  6  0  0  0
 25 26  1  0  0  0  0
 27 26  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 25 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C)[C@@H](C)[C@@]2([H])[C@]([H])(CC3=CC=CC=C3)NC(=O)[C@]22[C@H](O)\C=C\[C@H](C)[C@H](O)[C@@H](C)C\C=C\[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H37NO3/c1-17-9-8-12-22-15-19(3)20(4)25-23(16-21-10-6-5-7-11-21)29-27(32)28(22,25)24(30)14-13-18(2)26(17)31/h5-8,10-15,17-18,20,22-26,30-31H,9,16H2,1-4H3,(H,29,32)/b12-8+,14-13+/t17-,18-,20+,22?,23-,24+,25-,26?,28+/m0/s1

> <INCHI_KEY>
LMOPZIMULHEIJE-PZXJJAPDSA-N

> <FORMULA>
C28H37NO3

> <MOLECULAR_WEIGHT>
435.608

> <EXACT_MASS>
435.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.93763900347265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,6aS,10S,11R,12S,15R,15aS)-3-benzyl-11,15-dihydroxy-4,5,10,12-tetramethyl-1H,2H,3H,3aH,4H,6aH,9H,10H,11H,12H,15H-cycloundeca[d]isoindol-1-one

> <JCHEM_LOGP>
4.030889693333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.782179735909603

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.950294273638288

> <JCHEM_PKA_STRONGEST_BASIC>
-0.21798108149054782

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
131.35060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,6aS,10S,11R,12S,15R,15aS)-3-benzyl-11,15-dihydroxy-4,5,10,12-tetramethyl-2H,3H,3aH,4H,6aH,9H,10H,11H,12H,15H-cycloundeca[d]isoindol-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JAN-23         0                                  
HETATM    1  O   UNK     0      11.780   1.164   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.441   1.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.179   0.406   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.253  -0.698   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.655   0.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.407   1.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.871   2.209   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.554   0.999   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.218   3.785   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.200   2.289   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       4.859   3.046   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       7.868   1.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.115   0.169   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.078   2.641   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.899   1.339   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.291   4.114   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      10.708   3.513   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       7.428   4.737   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       7.164   6.254   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       8.620   4.194   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.068   5.118   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.498   4.547   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.718   3.023   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.160   2.482   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.701   4.046   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       3.983   2.684   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       5.057   1.580   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       3.597   1.089   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       4.869   0.052   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.451  -0.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.263  -2.079   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.846  -2.680   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.616  -1.753   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.804  -0.225   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.221   0.377   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.020   5.428   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18   25                                             
CONECT   10    9   11   12   27                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2   24                                                  
CONECT   24   23                                                            
CONECT   25    9   26   36                                                  
CONECT   26   25   27                                                       
CONECT   27   26   10   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   25                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₇NO₃

Average Mass

435.6080 Da

Monoisotopic Mass

435.27734 Da

IUPAC Name

(3S,3aR,4S,6aS,10S,11R,12S,15R,15aS)-3-benzyl-11,15-dihydroxy-4,5,10,12-tetramethyl-1H,2H,3H,3aH,4H,6aH,9H,10H,11H,12H,15H-cycloundeca[d]isoindol-1-one

Traditional Name

(3S,3aR,4S,6aS,10S,11R,12S,15R,15aS)-3-benzyl-11,15-dihydroxy-4,5,10,12-tetramethyl-2H,3H,3aH,4H,6aH,9H,10H,11H,12H,15H-cycloundeca[d]isoindol-1-one

CAS Registry Number

Not Available

SMILES

[H]C1=C(C)[C@@H](C)[C@@]2([H])[C@]([H])(CC3=CC=CC=C3)NC(=O)[C@]22[C@H](O)\C=C\[C@H](C)[C@H](O)[C@@H](C)C\C=C\[C@@]12[H]

InChI Identifier

InChI=1S/C28H37NO3/c1-17-9-8-12-22-15-19(3)20(4)25-23(16-21-10-6-5-7-11-21)29-27(32)28(22,25)24(30)14-13-18(2)26(17)31/h5-8,10-15,17-18,20,22-26,30-31H,9,16H2,1-4H3,(H,29,32)/b12-8+,14-13+/t17-,18-,20+,22?,23-,24+,25-,26?,28+/m0/s1

InChI Key

LMOPZIMULHEIJE-PZXJJAPDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Not Available	2024-05-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Not Available	2024-05-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Not Available	2024-05-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Not Available	2024-05-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Not Available	2024-05-04	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Not Available	2024-05-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D2O, experimental)	jittra.kor@biotec.or.th	Not Available	Not Available	2024-05-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
brunneum		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	4.03	ChemAxon
pKa (Strongest Acidic)	13.95	ChemAxon
pKa (Strongest Basic)	-0.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.35 m³·mol⁻¹	ChemAxon
Polarizability	49.94 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	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Brunnesin (NP0333051)

MOL for NP0333051 (Brunnesin)

3D MOL for NP0333051 (Brunnesin)

3D SDF for NP0333051 (Brunnesin)

3D-SDF for NP0333051 (Brunnesin)

PDB for NP0333051 (Brunnesin)

3D PDB for NP0333051 (Brunnesin)

SMILES for NP0333051 (Brunnesin)

INCHI for NP0333051 (Brunnesin)

Structure for NP0333051 (Brunnesin)

3D Structure for NP0333051 (Brunnesin)