MiMeDB: Showing metabocard for Fredericamycin A (MMDBc0016675)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:16:05 UTC

Update Date

2025-10-07 16:06:35 UTC

Metabolite ID

MMDBc0016675

Metabolite Identification

Common Name

Fredericamycin A

Description

Fredericamycin A is a natural antibiotic belonging to the chemical class of spirocyclic hydroquinones. Its unique structure features a quasi-symmetrical spirocyclic framework, which presents challenges for chemical synthesis (PMID:40271023 ). The total synthesis of fredericamycin A has been achieved through various innovative methods, including the assembly of multicyclic isoquinoline scaffolds from pyridines (PMID:34377413 ) and the use of stereoselective reactions (PMID:33522232 ). Notably, the first asymmetric synthesis of fredericamycin A has been reported alongside the synthesis of several other anthracycline antibiotics (PMID:32999145 ). Furthermore, synthetic approaches to its ABCD ring system have employed Claisen rearrangement and ring-closing metathesis as key steps (PMID:31656883 ). The production of fredericamycin A has also been enhanced in the deep-sea-derived Streptomyces somaliensis SCSIO ZH66 through ribosome engineering and response surface methodology, which activated its cryptic gene cluster (PMID:25927229 ). This compound is structurally related to fredericamycin C2 and is considered a potent lead in anticancer drug development (PMID:32481766 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109162D          

 44 49  0  0  1  0            999 V2000
    1.0733    4.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0035    3.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    4.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913    3.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118    2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3300   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1437   -0.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1503    0.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1311    1.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1171    2.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9491    0.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298    1.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106    2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6738    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7361    2.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5080    1.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8496    1.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4686    2.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5822    0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2012    1.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5273    0.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9119    2.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4064    0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6444    2.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3068    1.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0040    0.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875    1.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875    2.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2656    0.5987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4888    2.9698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0548    0.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5309    3.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7874    0.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2634    2.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8850    2.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1402   -0.5831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7991    1.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8657    3.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1793    3.5664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4503    4.9728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144    3.0009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4695    3.9713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336    1.9994    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 11  2  0  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 12  1  0  0  0  0
 23 16  1  0  0  0  0
 23 19  1  0  0  0  0
 24 18  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 21  1  0  0  0  0
 26 17  1  0  0  0  0
 26 22  2  0  0  0  0
 27 20  2  0  0  0  0
 28 21  2  0  0  0  0
 29 17  2  0  0  0  0
 30  8  1  1  0  0  0
 30 22  1  0  0  0  0
 30 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 14  2  0  0  0  0
 31 29  1  0  0  0  0
 32 15  2  0  0  0  0
 33 23  2  0  0  0  0
 34 24  2  0  0  0  0
 35 25  2  0  0  0  0
 36 26  1  0  0  0  0
 37 27  1  0  0  0  0
 38 28  1  0  0  0  0
 39 29  1  0  0  0  0
 40  2  1  0  0  0  0
 40 16  1  0  0  0  0
 41  3  1  0  0  0  0
 42  4  1  0  0  0  0
 43  5  1  0  0  0  0
 44  6  1  0  0  0  0
M  END


  Mrv1652305152109162D          

 44 49  0  0  1  0            999 V2000
    1.0733    4.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0035    3.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    4.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913    3.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118    2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3300   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1437   -0.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1503    0.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1311    1.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1171    2.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9491    0.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298    1.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106    2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6738    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7361    2.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5080    1.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8496    1.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4686    2.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5822    0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2012    1.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5273    0.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9119    2.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4064    0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6444    2.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3068    1.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0040    0.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875    1.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875    2.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2656    0.5987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4888    2.9698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0548    0.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5309    3.6383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7874    0.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2634    2.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8850    2.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1402   -0.5831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7991    1.9929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8657    3.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1793    3.5664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4503    4.9728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144    3.0009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4695    3.9713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5336    1.9994    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 11  2  0  0  0  0
 17 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 12  1  0  0  0  0
 23 16  1  0  0  0  0
 23 19  1  0  0  0  0
 24 18  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 21  1  0  0  0  0
 26 17  1  0  0  0  0
 26 22  2  0  0  0  0
 27 20  2  0  0  0  0
 28 21  2  0  0  0  0
 29 17  2  0  0  0  0
 30  8  1  1  0  0  0
 30 22  1  0  0  0  0
 30 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 14  2  0  0  0  0
 31 29  1  0  0  0  0
 32 15  2  0  0  0  0
 33 23  2  0  0  0  0
 34 24  2  0  0  0  0
 35 25  2  0  0  0  0
 36 26  1  0  0  0  0
 37 27  1  0  0  0  0
 38 28  1  0  0  0  0
 39 29  1  0  0  0  0
 40  2  1  0  0  0  0
 40 16  1  0  0  0  0
 41  3  1  0  0  0  0
 42  4  1  0  0  0  0
 43  5  1  0  0  0  0
 44  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016675

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C)=C(\[H])/C(/[H])=C(\[H])C1=NC(O)=C2C(O)=C3C(CC[C@@]33C(O)=C4C(=C3O)C(=O)C3=C(C(=O)C=C(OC)C3=O)C4=O)=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H21NO9/c1-3-4-5-6-14-10-13-9-12-7-8-30(22(12)26(36)17(13)29(39)31-14)27(37)20-21(28(30)38)25(35)19-18(24(20)34)15(32)11-16(40-2)23(19)33/h3-6,9-11,36-38H,7-8H2,1-2H3,(H,31,39)/b4-3+,6-5+/t30-/m0/s1

> <INCHI_KEY>
NJLAGDPRCAPJIF-MHSJTTIKSA-N

> <FORMULA>
C30H21NO9

> <MOLECULAR_WEIGHT>
539.496

> <EXACT_MASS>
539.12163126

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
55.67785428035616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-4,5,6',7',8,9-hexahydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.683203527666667

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.234400931129455

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6812606466671403

> <JCHEM_PKA_STRONGEST_BASIC>
5.523866777962565

> <JCHEM_POLAR_SURFACE_AREA>
171.31999999999996

> <JCHEM_REFRACTIVITY>
148.88960000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

> <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       2.004   8.570   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.407   6.590   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.495   8.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.906   6.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.397   6.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.809   4.831   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.816  -0.660   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.335  -0.406   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.614   1.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.711   2.961   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.752   3.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.105   0.706   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.202   2.576   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.300   4.445   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.925   2.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.041   5.358   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.282   3.674   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.386   2.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.675   4.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.020   1.529   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.309   2.895   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.184   1.805   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.502   5.426   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.559   1.462   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.136   4.194   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.773   3.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.941   0.430   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.790   2.641   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.870   5.158   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.562   1.118   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       8.379   5.544   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0      20.636   1.328   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.791   6.792   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      18.270   0.096   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      15.425   5.560   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      12.852   4.387   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.195  -1.088   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      12.692   3.720   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.949   6.257   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      20.868   6.657   0.000  0.00  0.00           O+0
HETATM   41  H   UNK     0       4.574   9.283   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.827   5.602   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.476   7.413   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.729   3.732   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   40                                                            
CONECT    3    1    4   41                                                  
CONECT    4    3    5   42                                                  
CONECT    5    4    6   43                                                  
CONECT    6    5   14   44                                                  
CONECT    7    8   12                                                       
CONECT    8    7   30                                                       
CONECT    9   12   13                                                       
CONECT   10   13   14                                                       
CONECT   11   15   16                                                       
CONECT   12    7    9   22                                                  
CONECT   13    9   10   17                                                  
CONECT   14    6   10   31                                                  
CONECT   15   11   18   32                                                  
CONECT   16   11   23   40                                                  
CONECT   17   13   26   29                                                  
CONECT   18   15   19   24                                                  
CONECT   19   18   23   25                                                  
CONECT   20   21   24   27                                                  
CONECT   21   20   25   28                                                  
CONECT   22   12   26   30                                                  
CONECT   23   16   19   33                                                  
CONECT   24   18   20   34                                                  
CONECT   25   19   21   35                                                  
CONECT   26   17   22   36                                                  
CONECT   27   20   30   37                                                  
CONECT   28   21   30   38                                                  
CONECT   29   17   31   39                                                  
CONECT   30    8   22   27   28                                             
CONECT   31   14   29                                                       
CONECT   32   15                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   25                                                            
CONECT   36   26                                                            
CONECT   37   27                                                            
CONECT   38   28                                                            
CONECT   39   29                                                            
CONECT   40    2   16                                                       
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    5                                                            
CONECT   44    6                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

Synonyms

Value	Source
FCRC-a48	MeSH

Molecular Formula

C₃₀H₂₁NO₉

Average Mass

539.496

Monoisotopic Mass

539.12163126

IUPAC Name

(2S)-1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-4,5,6',7',8,9-hexahydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

Traditional Name

(2S)-1,1',3,9'-tetrahydroxy-6-methoxy-3'-[(1E,3E)-penta-1,3-dien-1-yl]-6',7'-dihydrospiro[cyclopenta[b]naphthalene-2,8'-cyclopenta[g]isoquinoline]-4,5,8,9-tetrone

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(\[H])/C(/[H])=C(\[H])C1=NC(O)=C2C(O)=C3C(CC[C@@]33C(O)=C4C(=C3O)C(=O)C3=C(C(=O)C=C(OC)C3=O)C4=O)=CC2=C1

InChI Identifier

InChI=1S/C30H21NO9/c1-3-4-5-6-14-10-13-9-12-7-8-30(22(12)26(36)17(13)29(39)31-14)27(37)20-21(28(30)38)25(35)19-18(24(20)34)15(32)11-16(40-2)23(19)33/h3-6,9-11,36-38H,7-8H2,1-2H3,(H,31,39)/b4-3+,6-5+/t30-/m0/s1

InChI Key

NJLAGDPRCAPJIF-MHSJTTIKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Not Available

Direct Parent

Isoquinolines and derivatives

Alternative Parents

Substituents

Naphthalene
Isoquinoline
Indene
Indane
Anisole
1-hydroxy-4-unsubstituted benzenoid
Hydroxypyridine
Alkyl aryl ether
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Azacycle
Polyol
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	0.017 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.68	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	5.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	171.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	148.89 m³·mol⁻¹	ChemAxon
Polarizability	55.68 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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Bacteria	Actinobacteria	1		Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	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

C00018380

Chemspider ID

78439808

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135427349

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 Fredericamycin A (MMDBc0016675)

MOL for #<Metabolite:0x00007f8dc4a64178>

3D MOL for #<Metabolite:0x00007f8dc4a64178>

3D SDF for #<Metabolite:0x00007f8dc4a64178>

3D-SDF for #<Metabolite:0x00007f8dc4a64178>

PDB for #<Metabolite:0x00007f8dc4a64178>

3D PDB for #<Metabolite:0x00007f8dc4a64178>

SMILES for #<Metabolite:0x00007f8dc4a64178>

INCHI for #<Metabolite:0x00007f8dc4a64178>

Structure for #<Metabolite:0x00007f8dc4a64178>

3D Structure for #<Metabolite:0x00007f8dc4a64178>