NP-MRD: Showing NP-Card for n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid (NP0223384)

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Record Information

Version

2.0

Created at

2022-09-06 01:27:43 UTC

Updated at

2022-09-06 01:27:43 UTC

NP-MRD ID

NP0223384

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid

Description

Dactinomycin, also known as cosmegen or actd, belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Dactinomycin is a drug which is used for the treatment of wilms' tumor, childhood rhabdomyosarcoma, ewing's sarcoma and metastatic, nonseminomatous testicular cancer as part of a combination chemotherapy and/or multi-modality treatment regimen. Dactinomycin is in the cytotoxic antibiotic family of medications. Dactinomycin is an extremely weak basic (essentially neutral) compound (based on its pKa). Because actinomycin can bind DNA duplexes, it can also interfere with DNA replication, although other chemicals such as hydroxyurea are better suited for use in the laboratory as inhibitors of DNA synthesis. Actinomycin D does this by binding DNA at the transcription initiation complex and preventing elongation of RNA chain by RNA polymerase. It was first isolated by Selman Waksman and his co-worker H. Boyd Woodruff in 1940. Use in pregnancy may harm the baby. n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid is found in Streptomyces anulatus, Streptomyces flavogriseus, Streptomyces flavovirens, Streptomyces heliomycini, Streptomyces lividans, Streptomyces mutabilis, Streptomyces parvulus and Streptomyces violascens. n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid was first documented in 1985 (PMID: 2410919). The wholesale cost in the developing world is about US$24.73 Per 500 mcg vial (PMID: 15543019) (PMID: 16803542) (PMID: 17102824).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04191212152D          

 92 98  0  0  0  0            999 V2000
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M  END

     RDKit          3D

176182  0  0  0  0  0  0  0  0999 V2000
   -2.0810   -3.7045    6.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 04191212152D          

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    2.8579    7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0223384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@H](NC(=O)[C@@H](NC(=O)C1=C3N=C4C(OC3=C(C)C=C1)=C(C)C(=O)C(N)=C4C(=O)N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@]3([H])CCCN3C(=O)[C@H](NC1=O)C(C)C)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C2=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1

> <INCHI_KEY>
RJURFGZVJUQBHK-IIXSONLDSA-N

> <FORMULA>
C62H86N12O16

> <MOLECULAR_WEIGHT>
1255.417

> <EXACT_MASS>
1254.628474764

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
129.20305434085913

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N1,N9-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-bis(propan-2-yl)-hexadecahydro-1H-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
-0.09688245333333306

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.098483446604181

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.516916377159324

> <JCHEM_PKA_STRONGEST_BASIC>
-0.12943168000481753

> <JCHEM_POLAR_SURFACE_AREA>
355.53999999999996

> <JCHEM_REFRACTIVITY>
326.17160000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
actinomycin D

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      -4.001   3.850   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.668   5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -9.336  13.090   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -9.656  14.596   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.669  12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -11.187  14.757   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -11.814  13.350   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0     -11.945  11.457   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0     -12.003  10.010   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -13.337  10.780   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -10.669   7.700   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -9.336   8.470   0.000  0.00  0.00           O+0
HETATM   41  N   UNK     0     -10.669   6.160   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0     -12.003   5.390   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -9.336   5.390   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -10.669   3.080   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.002   3.080   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -9.336  10.010   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -8.002   7.700   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   52  N   UNK     0      -2.667  12.320   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -6.668  16.170   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -4.001  16.170   0.000  0.00  0.00           C+0
HETATM   58  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   59  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   64  N   UNK     0       9.336  13.090   0.000  0.00  0.00           N+0
HETATM   65  C   UNK     0       9.656  14.596   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      10.669  12.320   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      11.187  14.757   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      11.814  13.350   0.000  0.00  0.00           C+0
HETATM   69  H   UNK     0      11.945  11.457   0.000  0.00  0.00           H+0
HETATM   70  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   71  N   UNK     0      12.003  10.010   0.000  0.00  0.00           N+0
HETATM   72  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      10.669   7.700   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   76  N   UNK     0      10.669   6.160   0.000  0.00  0.00           N+0
HETATM   77  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   82  O   UNK     0       9.336  10.010   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0       8.002   7.700   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   87  N   UNK     0       2.667  12.320   0.000  0.00  0.00           N+0
HETATM   88  C   UNK     0       8.002  12.320   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0       6.668  16.170   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0       5.335  15.400   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0       4.001  16.170   0.000  0.00  0.00           C+0
CONECT    1    7    2    6                                                  
CONECT    2    1    8    3                                                  
CONECT    3    2    5                                                       
CONECT    4   15    5    6                                                  
CONECT    5    3    4   16                                                  
CONECT    6    4    1                                                       
CONECT    7    1    9   10                                                  
CONECT    8    2   11   12                                                  
CONECT    9    7   58   13                                                  
CONECT   10    7   14   11                                                  
CONECT   11    8   10   17                                                  
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15    4   18   19                                                  
CONECT   16    5   20   21                                                  
CONECT   17   11                                                            
CONECT   18   15   23   22                                                  
CONECT   19   15   20                                                       
CONECT   20   16   19                                                       
CONECT   21   16                                                            
CONECT   22   18                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   51   52                                                  
CONECT   26   24   49   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   48   43                                                  
CONECT   29   53   30   31                                                  
CONECT   30   29   32                                                       
CONECT   31   29   33   34   35                                             
CONECT   32   30   33                                                       
CONECT   33   31   32                                                       
CONECT   34   31                                                            
CONECT   35   31   47   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36   39                                                       
CONECT   38   36                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   28   41   44                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   35                                                            
CONECT   48   28                                                            
CONECT   49   26                                                            
CONECT   50   53                                                            
CONECT   51   25                                                            
CONECT   52   25   54                                                       
CONECT   53   29   50   54                                                  
CONECT   54   52   53   56                                                  
CONECT   55   56                                                            
CONECT   56   54   55   57                                                  
CONECT   57   56                                                            
CONECT   58    9   59                                                       
CONECT   59   58   60   61                                                  
CONECT   60   59   86   87                                                  
CONECT   61   59   84   62                                                  
CONECT   62   61   63                                                       
CONECT   63   62   83   78                                                  
CONECT   64   88   65   66                                                  
CONECT   65   64   67                                                       
CONECT   66   64   68   69   70                                             
CONECT   67   65   68                                                       
CONECT   68   66   67                                                       
CONECT   69   66                                                            
CONECT   70   66   82   71                                                  
CONECT   71   70   72   73                                                  
CONECT   72   71   74                                                       
CONECT   73   71                                                            
CONECT   74   72   75   76                                                  
CONECT   75   74                                                            
CONECT   76   74   77   78                                                  
CONECT   77   76                                                            
CONECT   78   63   76   79                                                  
CONECT   79   78   80   81                                                  
CONECT   80   79                                                            
CONECT   81   79                                                            
CONECT   82   70                                                            
CONECT   83   63                                                            
CONECT   84   61                                                            
CONECT   85   88                                                            
CONECT   86   60                                                            
CONECT   87   60   89                                                       
CONECT   88   64   85   89                                                  
CONECT   89   87   88   91                                                  
CONECT   90   91                                                            
CONECT   91   89   90   92                                                  
CONECT   92   91                                                            
MASTER        0    0    0    0    0    0    0    0   92    0  196    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-N,n'-bis(hexadecahydro-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxo-1H-pyrrolo(2,1-i)(1,4,7,10,13)oxatetra-azacyclohexadecin-10-yl)-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide	ChEBI
ActD	ChEBI
Actinomycin C1	ChEBI
Actinomycin IV	ChEBI
Actinomycin D	HMDB
Ac-de	HMDB
Cosmegen	HMDB
Lyovac, cosmegen	HMDB
MSD Brand OF dactinomycin	HMDB
Lemery brand OF dactinomycin	HMDB
Lyovac-cosmegen	HMDB
Merck brand OF dactinomycin	HMDB
Merck sharp and dohme brand OF dactinomycin	HMDB
Cosmegen lyovac	HMDB
Meractinomycin	HMDB
Actinomycin	HMDB
Merck frosst brand OF dactinomycin	HMDB
Lyovac cosmegen	HMDB
LyovacCosmegen	HMDB
Dactinomycin	ChEBI

Chemical Formula

C₆₂H₈₆N₁₂O₁₆

Average Mass

1255.4170 Da

Monoisotopic Mass

1254.62847 Da

IUPAC Name

N1,N9-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-bis(propan-2-yl)-hexadecahydro-1H-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide

Traditional Name

actinomycin D

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCCN1C(=O)[C@H](NC(=O)[C@@H](NC(=O)C1=C3N=C4C(OC3=C(C)C=C1)=C(C)C(=O)C(N)=C4C(=O)N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@]3([H])CCCN3C(=O)[C@H](NC1=O)C(C)C)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C2=O)C(C)C

InChI Identifier

InChI=1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1

InChI Key

RJURFGZVJUQBHK-IIXSONLDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Streptomyces anulatus	LOTUS Database	35616633
Streptomyces flavogriseus	LOTUS Database	35616633
Streptomyces flavovirens	LOTUS Database	35616633
Streptomyces heliomycini	LOTUS Database	35616633
Streptomyces lividans	LOTUS Database	35616633
Streptomyces mutabilis	LOTUS Database	35616633
Streptomyces parvulus	LOTUS Database	35616633
Streptomyces violascens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Phenoxazine
Alpha-amino acid ester
Macrolactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Vinylogous amide
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Cyclic ketone
Secondary carboxylic acid amide
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

actinomycin (CHEBI:27666 )

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	2.76	ALOGPS
logP	-0.097	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.52	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	355.54 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	326.17 m³·mol⁻¹	ChemAxon
Polarizability	129.2 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015105

DrugBank ID

DB00970

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10482167

KEGG Compound ID

C06770

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dactinomycin

METLIN ID

Not Available

PubChem Compound

457193

PDB ID

Not Available

ChEBI ID

27666

Good Scents ID

Not Available

References

General References

Sobell HM: Actinomycin and DNA transcription. Proc Natl Acad Sci U S A. 1985 Aug;82(16):5328-31. doi: 10.1073/pnas.82.16.5328. [PubMed:2410919 ]
Khatua S, Nair CN, Ghosh K: Immune-mediated thrombocytopenia following dactinomycin therapy in a child with alveolar rhabdomyosarcoma: the unresolved issues. J Pediatr Hematol Oncol. 2004 Nov;26(11):777-9. doi: 10.1097/00043426-200411000-00020. [PubMed:15543019 ]
Turan T, Karacay O, Tulunay G, Boran N, Koc S, Bozok S, Kose MF: Results with EMA/CO (etoposide, methotrexate, actinomycin D, cyclophosphamide, vincristine) chemotherapy in gestational trophoblastic neoplasia. Int J Gynecol Cancer. 2006 May-Jun;16(3):1432-8. doi: 10.1111/j.1525-1438.2006.00606.x. [PubMed:16803542 ]
Abd El-Aal HH, Habib EE, Mishrif MM: Wilms' tumor: the experience of the pediatric unit of Kasr El-Aini center of radiation oncology and nuclear medicine (NEMROCK). J Egypt Natl Canc Inst. 2005 Dec;17(4):308-14. [PubMed:17102824 ]
LOTUS database [Link]

Showing NP-Card for n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid (NP0223384)

MOL for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

3D MOL for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

3D SDF for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

3D-SDF for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

PDB for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

3D PDB for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

SMILES for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

INCHI for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

Structure for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)

3D Structure for NP0223384 (n1,n9-bis[(6s,9r,10s,13r,18as)-11-hydroxy-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,14-tetraoxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxophenoxazine-1,9-dicarboximidic acid)