MiMeDB: Showing metabocard for Penochalasin C (MMDBc0009115)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:44:27 UTC

Update Date

2022-08-31 06:29:35 UTC

Metabolite ID

MMDBc0009115

Metabolite Identification

Common Name

Penochalasin C

Description

Penochalasin C belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. Penochalasin C is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103442D          

 47 52  0  0  1  0            999 V2000
    1.5979   -3.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812   -2.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6394    1.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9591    3.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1499   -1.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7758    2.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -0.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4966    3.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455    0.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034    1.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4959   -1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0760    2.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515    4.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -2.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3188   -1.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1770    1.0957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5374    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    3.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3133    3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2520   -0.2707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6737    3.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    1.8056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9695    0.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541    1.1546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6792   -0.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749   -0.3296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9011    0.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084    0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0793    4.3934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -0.1528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285    1.5247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021   -0.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4353   -1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5520    0.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728   -1.7549    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -0.8949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730   -1.6370    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -3.0623    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9998    1.0368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124   -1.0128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573    1.9616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -0.3885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  6  1  0  0  0  0
 13 12  1  0  0  0  0
 17  1  1  1  0  0  0
 17  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  2  0  0  0  0
 19  3  1  1  0  0  0
 20  4  2  0  0  0  0
 20 19  1  0  0  0  0
 21 15  1  0  0  0  0
 21 16  2  0  0  0  0
 22  9  2  0  0  0  0
 22 21  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  2  0  0  0  0
 24 22  1  0  0  0  0
 25 12  2  0  0  0  0
 26 15  1  6  0  0  0
 27 13  2  0  0  0  0
 28 19  1  0  0  0  0
 28 26  1  0  0  0  0
 29 18  1  0  0  0  0
 29 25  1  0  0  0  0
 30 20  1  0  0  0  0
 30 23  1  0  0  0  0
 32 23  1  0  0  0  0
 32 27  1  6  0  0  0
 32 28  1  0  0  0  0
 32 31  1  0  0  0  0
 33 16  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  1  0  0  0  0
 34 27  1  0  0  0  0
 35 26  1  0  0  0  0
 35 31  2  0  0  0  0
 36 29  2  0  0  0  0
 30 37  1  6  0  0  0
 38 31  1  0  0  0  0
 39  7  1  0  0  0  0
 40 10  1  0  0  0  0
 41 14  1  0  0  0  0
 17 42  1  6  0  0  0
 19 43  1  6  0  0  0
 23 44  1  6  0  0  0
 26 45  1  1  0  0  0
 28 46  1  6  0  0  0
 30 47  1  1  0  0  0
M  END


  Mrv1652305152103442D          

 47 52  0  0  1  0            999 V2000
    1.5979   -3.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812   -2.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6394    1.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9591    3.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1499   -1.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7758    2.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -0.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4966    3.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455    0.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034    1.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4959   -1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0760    2.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515    4.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -2.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3188   -1.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1770    1.0957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5374    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    3.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3133    3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2520   -0.2707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6737    3.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    1.8056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9695    0.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541    1.1546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6792   -0.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749   -0.3296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9011    0.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1084    0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0793    4.3934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -0.1528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285    1.5247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021   -0.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4353   -1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5520    0.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728   -1.7549    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -0.8949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730   -1.6370    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -3.0623    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9998    1.0368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6124   -1.0128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6573    1.9616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -0.3885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  6  1  0  0  0  0
 13 12  1  0  0  0  0
 17  1  1  1  0  0  0
 17  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  2  0  0  0  0
 19  3  1  1  0  0  0
 20  4  2  0  0  0  0
 20 19  1  0  0  0  0
 21 15  1  0  0  0  0
 21 16  2  0  0  0  0
 22  9  2  0  0  0  0
 22 21  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  2  0  0  0  0
 24 22  1  0  0  0  0
 25 12  2  0  0  0  0
 26 15  1  6  0  0  0
 27 13  2  0  0  0  0
 28 19  1  0  0  0  0
 28 26  1  0  0  0  0
 29 18  1  0  0  0  0
 29 25  1  0  0  0  0
 30 20  1  0  0  0  0
 30 23  1  0  0  0  0
 32 23  1  0  0  0  0
 32 27  1  6  0  0  0
 32 28  1  0  0  0  0
 32 31  1  0  0  0  0
 33 16  1  0  0  0  0
 33 24  1  0  0  0  0
 34 25  1  0  0  0  0
 34 27  1  0  0  0  0
 35 26  1  0  0  0  0
 35 31  2  0  0  0  0
 36 29  2  0  0  0  0
 30 37  1  6  0  0  0
 38 31  1  0  0  0  0
 39  7  1  0  0  0  0
 40 10  1  0  0  0  0
 41 14  1  0  0  0  0
 17 42  1  6  0  0  0
 19 43  1  6  0  0  0
 23 44  1  6  0  0  0
 26 45  1  1  0  0  0
 28 46  1  6  0  0  0
 30 47  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009115

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C1=C([H])/[C@@]2([H])[C@]([H])(O)C(=C)[C@@]([H])(C)[C@@]3([H])[C@]([H])(CC4=CNC5=CC=CC=C45)N=C(O)[C@@]23C2=CC=C(N2)C(=O)C(C)=C([H])[C@@]([H])(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H35N3O3/c1-17-8-7-10-23-30(37)20(4)19(3)28-26(15-21-16-33-24-11-6-5-9-22(21)24)35-31(38)32(23,28)27-13-12-25(34-27)29(36)18(2)14-17/h5-7,9-14,16-17,19,23,26,28,30,33-34,37H,4,8,15H2,1-3H3,(H,35,38)/b10-7+,18-14+/t17-,19+,23-,26-,28-,30+,32+/m0/s1

> <INCHI_KEY>
CYRVQOQBMLPFPT-XJBGXHEWSA-N

> <FORMULA>
C32H35N3O3

> <MOLECULAR_WEIGHT>
509.65

> <EXACT_MASS>
509.267841999

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.94892544082093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,6R,7S,9S,10R,11E,14S,15E)-3,9-dihydroxy-5-[(1H-indol-3-yl)methyl]-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0^{2,6}.0^{2,10}]henicosa-1(20),3,11,15,18-pentaen-17-one

> <ALOGPS_LOGP>
5.03

> <JCHEM_LOGP>
4.245632854239527

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.378479540184678

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1506500962450223

> <JCHEM_PKA_STRONGEST_BASIC>
5.58851990045474

> <JCHEM_POLAR_SURFACE_AREA>
101.47

> <JCHEM_REFRACTIVITY>
151.4675

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,6R,7S,9S,10R,11E,14S,15E)-3,9-dihydroxy-5-(1H-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0^{2,6}.0^{2,10}]henicosa-1(20),3,11,15,18-pentaen-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       2.983  -5.606   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.192  -4.111   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.060   3.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.406   0.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.851   4.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.524   5.968   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.280  -3.166   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.583  -4.441   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.315   4.473   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.393  -1.781   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.660   7.243   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.192   1.427   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.806   2.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.792  -2.946   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.142   4.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.656   7.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.119  -4.331   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.328  -2.836   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.197   2.045   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.870   0.660   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.926   5.960   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.452   5.748   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.470  -0.505   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.124   7.133   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.138  -0.175   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.285   3.370   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.810   0.784   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.661   2.155   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.001  -1.451   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.006  -0.615   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.682   1.307   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.202   0.880   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       2.015   8.201   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       2.602  -0.285   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       1.733   2.846   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0       6.537  -1.341   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.679  -2.001   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.897   0.361   0.000  0.00  0.00           O+0
HETATM   39  H   UNK     0      -1.816  -3.276   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.929  -1.671   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.256  -3.056   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.447  -5.716   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.733   1.935   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.143  -1.891   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.227   3.662   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.543  -0.725   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5    6    9                                                       
CONECT    6    5   11                                                       
CONECT    7    8   10   39                                                  
CONECT    8    7   17                                                       
CONECT    9    5   22                                                       
CONECT   10    7   23   40                                                  
CONECT   11    6   24                                                       
CONECT   12   13   25                                                       
CONECT   13   12   27                                                       
CONECT   14   17   18   41                                                  
CONECT   15   21   26                                                       
CONECT   16   21   33                                                       
CONECT   17    1    8   14   42                                             
CONECT   18    2   14   29                                                  
CONECT   19    3   20   28   43                                             
CONECT   20    4   19   30                                                  
CONECT   21   15   16   22                                                  
CONECT   22    9   21   24                                                  
CONECT   23   10   30   32   44                                             
CONECT   24   11   22   33                                                  
CONECT   25   12   29   34                                                  
CONECT   26   15   28   35   45                                             
CONECT   27   13   32   34                                                  
CONECT   28   19   26   32   46                                             
CONECT   29   18   25   36                                                  
CONECT   30   20   23   37   47                                             
CONECT   31   32   35   38                                                  
CONECT   32   23   27   28   31                                             
CONECT   33   16   24                                                       
CONECT   34   25   27                                                       
CONECT   35   26   31                                                       
CONECT   36   29                                                            
CONECT   37   30                                                            
CONECT   38   31                                                            
CONECT   39    7                                                            
CONECT   40   10                                                            
CONECT   41   14                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   23                                                            
CONECT   45   26                                                            
CONECT   46   28                                                            
CONECT   47   30                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

Synonyms

Not Available

Molecular Formula

C₃₂H₃₅N₃O₃

Average Mass

509.65

Monoisotopic Mass

509.267841999

IUPAC Name

(2R,5S,6R,7S,9S,10R,11E,14S,15E)-3,9-dihydroxy-5-[(1H-indol-3-yl)methyl]-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0^{2,6}.0^{2,10}]henicosa-1(20),3,11,15,18-pentaen-17-one

Traditional Name

(2R,5S,6R,7S,9S,10R,11E,14S,15E)-3,9-dihydroxy-5-(1H-indol-3-ylmethyl)-7,14,16-trimethyl-8-methylidene-4,21-diazatetracyclo[16.2.1.0^{2,6}.0^{2,10}]henicosa-1(20),3,11,15,18-pentaen-17-one

CAS Registry Number

Not Available

SMILES

[H]\C1=C([H])/[C@@]2([H])[C@]([H])(O)C(=C)[C@@]([H])(C)[C@@]3([H])[C@]([H])(CC4=CNC5=CC=CC=C45)N=C(O)[C@@]23C2=CC=C(N2)C(=O)C(C)=C([H])[C@@]([H])(C)C1

InChI Identifier

InChI=1S/C32H35N3O3/c1-17-8-7-10-23-30(37)20(4)19(3)28-26(15-21-16-33-24-11-6-5-9-22(21)24)35-31(38)32(23,28)27-13-12-25(34-27)29(36)18(2)14-17/h5-7,9-14,16-17,19,23,26,28,30,33-34,37H,4,8,15H2,1-3H3,(H,35,38)/b10-7+,18-14+/t17-,19+,23-,26-,28-,30+,32+/m0/s1

InChI Key

CYRVQOQBMLPFPT-XJBGXHEWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Isoindolone
3-alkylindole
Indole
Indole or derivatives
Isoindoline
Isoindole or derivatives
Aryl ketone
Pyrrolidone
Benzenoid
2-pyrrolidone
Substituted pyrrole
Cyclic alcohol
Heteroaromatic compound
Pyrrole
Pyrrolidine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Ketone
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0021 g/L	ALOGPS
logP	5.03	ALOGPS
logP	4.25	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	5.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	101.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	151.47 m³·mol⁻¹	ChemAxon
Polarizability	56.95 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8499499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10324036

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Penochalasin C (MMDBc0009115)

MOL for #<Metabolite:0x00007fecd32363c0>

3D MOL for #<Metabolite:0x00007fecd32363c0>

3D SDF for #<Metabolite:0x00007fecd32363c0>

3D-SDF for #<Metabolite:0x00007fecd32363c0>

PDB for #<Metabolite:0x00007fecd32363c0>

3D PDB for #<Metabolite:0x00007fecd32363c0>

SMILES for #<Metabolite:0x00007fecd32363c0>

INCHI for #<Metabolite:0x00007fecd32363c0>

Structure for #<Metabolite:0x00007fecd32363c0>

3D Structure for #<Metabolite:0x00007fecd32363c0>