NP-MRD: Showing NP-Card for Cyrneine A (NP0006487)

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Record Information

Version

1.0

Created at

2020-12-09 03:29:31 UTC

Updated at

2021-07-15 16:54:56 UTC

NP-MRD ID

NP0006487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyrneine A

Provided By

NPAtlas

Description

Cyrneine A is found in Sarcodon cyrneus. It was first documented in 2006 (PMID: 16881016). Based on a literature review a significant number of articles have been published on Cyrneine a (PMID: 17320402) (PMID: 30793912) (PMID: 29858575) (PMID: 22431475) (PMID: 17337280).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118283D          

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     RDKit          3D

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   -3.5488   -0.7886   -0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23  4  1  0  0  0  0
 19  5  1  0  0  0  0
 15  6  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  2 27  1  6  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8 32  1  0  0  0  0
 10 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  6  0  0  0
 14 37  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 21 48  1  1  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])C(=C2C3=C([H])C([H])=C(C([H])=O)C([H])([H])[C@]([H])(O[H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-12(2)14-10-17(23)20(4)8-7-19(3)15(18(14)20)6-5-13(11-21)9-16(19)22/h5-6,11-12,16-17,22-23H,7-10H2,1-4H3/t16-,17+,19+,20-/m0/s1

> <INCHI_KEY>
IXBCZHOTZLYJDA-CUDHKJQZSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.06566970819283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR,5aR,6S)-3,6-dihydroxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
1.8830893680000003

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.535208155337724

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.5483745583253

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8150287637361436

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
93.90319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyrneine A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -2.8829    2.5922    0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353    1.8938   -0.0508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9353    2.0017   -1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    0.4663    0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7873   -0.2453    0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    0.0400    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    1.2429    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809    1.8746    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440    1.5717    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118    2.3717    0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993    3.2455    1.3600 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692    0.6169   -0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3538   -0.2953   -1.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4697    0.4366   -2.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6610   -0.9590   -0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7136   -1.1322    0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943   -2.3017   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -2.6154    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144   -1.7180    0.3136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8156   -1.9722   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3610   -1.6054    1.2156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1890   -2.6982    1.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800   -0.4349    0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7267    3.7025    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798    2.3534    2.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9652    2.4260    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1733    2.4640   -0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8072    1.3551   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874    3.0534   -1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3148    1.7255   -2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018    1.7209    1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2351    2.6345    1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727    2.2551   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    0.1186   -0.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744    1.2390   -1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065   -1.0749   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657    0.6224   -3.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809   -2.1060    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6671   -1.3371    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -0.3025    1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -2.4579   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8572   -3.0780   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -2.6210    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3942   -3.6577    0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9486   -1.0460   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739   -2.5276   -1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511   -2.6299   -1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -1.2016    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9249   -3.2732    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056    0.0549    1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488   -0.7886   -0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23  4  1  0
 19  5  1  0
 15  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  6
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.883   2.592   0.981  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.035   1.894  -0.051  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.935   2.002  -1.347  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.876   0.466   0.186  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.787  -0.245   0.295  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.618   0.040   0.257  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.852   1.243   0.753  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.181   1.875   0.858  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.244   1.572   0.110  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.412   2.372   0.455  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.399   3.245   1.360  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.469   0.617  -0.969  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.354  -0.295  -1.332  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.470   0.437  -2.152  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.661  -0.959  -0.206  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.714  -1.132   0.911  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.094  -2.302  -0.393  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.102  -2.615   0.482  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.214  -1.718   0.314  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.816  -1.972  -1.096  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.361  -1.605   1.216  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.189  -2.698   1.278  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.080  -0.435   0.469  0.00  0.00           C+0
HETATM   24  H   UNK     0      -2.727   3.703   0.847  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.580   2.353   2.018  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.965   2.426   0.842  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.173   2.464  -0.419  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.807   1.355  -1.230  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.287   3.053  -1.371  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.315   1.726  -2.222  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.002   1.721   1.147  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.235   2.635   1.611  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.373   2.255  -0.059  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.446   0.119  -0.782  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.674   1.239  -1.897  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.807  -1.075  -2.015  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.966   0.622  -3.005  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.481  -2.106   1.427  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.667  -1.337   0.380  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.739  -0.303   1.611  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.801  -2.458  -1.444  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.857  -3.078  -0.179  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.265  -2.621   1.528  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.394  -3.658   0.244  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.949  -1.046  -1.645  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.774  -2.528  -1.016  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.151  -2.630  -1.688  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.097  -1.202   2.225  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.925  -3.273   2.039  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.806   0.055   1.113  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.549  -0.789  -0.437  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3    4   27                                             
CONECT    3    2   28   29   30                                             
CONECT    4    2    5   23                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   31                                                  
CONECT    8    7    9   32                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11   33                                                  
CONECT   11   10                                                            
CONECT   12    9   13   34   35                                             
CONECT   13   12   14   15   36                                             
CONECT   14   13   37                                                       
CONECT   15   13   16   17    6                                             
CONECT   16   15   38   39   40                                             
CONECT   17   15   18   41   42                                             
CONECT   18   17   19   43   44                                             
CONECT   19   18   20   21    5                                             
CONECT   20   19   45   46   47                                             
CONECT   21   19   22   23   48                                             
CONECT   22   21   49                                                       
CONECT   23   21    4   50   51                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33   10                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   16                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

RDKit          3D

51 53  0  0  0  0  0  0  0  0999 V2000
   -2.8829    2.5922    0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0353    1.8938   -0.0508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9353    2.0017   -1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    0.4663    0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7873   -0.2453    0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6175    0.0400    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    1.2429    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809    1.8746    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440    1.5717    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118    2.3717    0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993    3.2455    1.3600 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692    0.6169   -0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3538   -0.2953   -1.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4697    0.4366   -2.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6610   -0.9590   -0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7136   -1.1322    0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943   -2.3017   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -2.6154    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144   -1.7180    0.3136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8156   -1.9722   -1.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3610   -1.6054    1.2156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1890   -2.6982    1.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800   -0.4349    0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7267    3.7025    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798    2.3534    2.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9652    2.4260    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1733    2.4640   -0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8072    1.3551   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874    3.0534   -1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3148    1.7255   -2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0018    1.7209    1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2351    2.6345    1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3727    2.2551   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463    0.1186   -0.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744    1.2390   -1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065   -1.0749   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657    0.6224   -3.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809   -2.1060    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6671   -1.3371    0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -0.3025    1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -2.4579   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8572   -3.0780   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -2.6210    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3942   -3.6577    0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9486   -1.0460   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739   -2.5276   -1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511   -2.6299   -1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -1.2016    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9249   -3.2732    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056    0.0549    1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5488   -0.7886   -0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23  4  1  0
 19  5  1  0
 15  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  6
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
1,14-Dihydroxycyantha-3,5(10),11-triene-12-carbaldehyde	MeSH

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(3R,3aR,5aR,6S)-3,6-dihydroxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde

Traditional Name

cyrneine A

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2C3=CC=C(C[C@H](O)[C@]3(C)CC[C@@]2(C)[C@H](O)C1)C=O

InChI Identifier

InChI=1S/C20H28O3/c1-12(2)14-10-17(23)20(4)8-7-19(3)15(18(14)20)6-5-13(11-21)9-16(19)22/h5-6,11-12,16-17,22-23H,7-10H2,1-4H3/t16-,17+,19+,20-/m0/s1

InChI Key

IXBCZHOTZLYJDA-CUDHKJQZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sarcodon cyrneus	NPAtlas	16881016

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	3.37	ALOGPS
logP	1.88	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	-0.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.9 m³·mol⁻¹	ChemAxon
Polarizability	36.07 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	No	ChemAxon

External Links

NPAtlas ID

NPA011935

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10172891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12000424

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Marcotullio MC, Pagiott R, Maltese F, Obara Y, Hoshino T, Nakahata N, Curini M: Neurite outgrowth activity of cyathane diterpenes from Sarcodon cyrneus, cyrneines A and B. Planta Med. 2006 Jul;72(9):819-23. doi: 10.1055/s-2006-946681. [PubMed:16881016 ]
Marcotullio MC, Pagiotti R, Maltese F, Oball-Mond Mwankie GN, Hoshino T, Obara Y, Nakahata N: Cyathane diterpenes from Sarcodon cyrneus and evaluation of their activities of neuritegenesis and nerve growth factor production. Bioorg Med Chem. 2007 Apr 15;15(8):2878-82. doi: 10.1016/j.bmc.2007.02.019. Epub 2007 Feb 13. [PubMed:17320402 ]
Wu GJ, Zhang YH, Tan DX, He L, Cao BC, He YP, Han FS: Synthetic Studies on Enantioselective Total Synthesis of Cyathane Diterpenoids: Cyrneines A and B, Glaucopine C, and (+)-Allocyathin B2. J Org Chem. 2019 Mar 15;84(6):3223-3238. doi: 10.1021/acs.joc.8b03138. Epub 2019 Mar 4. [PubMed:30793912 ]
Wu GJ, Zhang YH, Tan DX, Han FS: Total synthesis of cyrneines A-B and glaucopine C. Nat Commun. 2018 Jun 1;9(1):2148. doi: 10.1038/s41467-018-04480-6. [PubMed:29858575 ]
Elamparuthi E, Fellay C, Neuburger M, Gademann K: Total synthesis of cyrneine A. Angew Chem Int Ed Engl. 2012 Apr 23;51(17):4071-3. doi: 10.1002/anie.201200515. Epub 2012 Mar 16. [PubMed:22431475 ]
Obara Y, Hoshino T, Marcotullio MC, Pagiotti R, Nakahata N: A novel cyathane diterpene, cyrneine A, induces neurite outgrowth in a Rac1-dependent mechanism in PC12 cells. Life Sci. 2007 Apr 10;80(18):1669-77. doi: 10.1016/j.lfs.2007.01.057. Epub 2007 Feb 12. [PubMed:17337280 ]

Showing NP-Card for Cyrneine A (NP0006487)

MOL for NP0006487 (Cyrneine A)

3D MOL for NP0006487 (Cyrneine A)

3D SDF for NP0006487 (Cyrneine A)

3D-SDF for NP0006487 (Cyrneine A)

PDB for NP0006487 (Cyrneine A)

3D PDB for NP0006487 (Cyrneine A)

SMILES for NP0006487 (Cyrneine A)

INCHI for NP0006487 (Cyrneine A)

Structure for NP0006487 (Cyrneine A)

3D Structure for NP0006487 (Cyrneine A)