NP-MRD: Showing NP-Card for 9-Aminocamptothecin (NP0137176)

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Record Information

Version

2.0

Created at

2022-05-30 16:44:03 UTC

Updated at

2022-05-30 16:44:03 UTC

NP-MRD ID

NP0137176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Aminocamptothecin

Description

9-Aminocamptothecin belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). 9-Aminocamptothecin was first documented in 2013 (PMID: 23791639). Based on a literature review a small amount of articles have been published on 9-Aminocamptothecin (PMID: 26824303) (PMID: 25277385) (PMID: 24889073) (PMID: 24297599).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305302218442D          

 27 31  0  0  0  0            999 V2000
    5.4176   -1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9255   -1.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6165   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9168   -0.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9755   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784    0.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1264    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    1.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929    1.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255    1.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8804    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.0694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    2.4233    0.0000 O   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 15 25  1  0  0  0  0
 13 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -3.5336   -1.6785    1.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9298   -1.5033    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9038   -0.0813   -0.4543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3019   -0.0991   -1.8117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8775    0.7646    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7647    0.2427    0.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7819    2.1363    0.1273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381    2.7318   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4967    1.9222   -0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5834    0.5446   -0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.1811   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959    0.4922   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1535    1.8229   -0.3315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940    2.5773   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    3.8267   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136    2.2442   -0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    1.0004   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696    0.7930    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7833   -0.5216    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608   -0.7583    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0746    0.3311    0.2481 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6543   -2.0347    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7634   -3.1006    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4072   -2.8667    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9064   -1.5864    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783   -1.3535    0.0530 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1448   -0.0798   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4451   -1.6854    2.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0278   -2.6588    1.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825   -0.8649    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9828   -1.8660   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071   -2.1412   -0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5539   -0.3341   -2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961    2.7412   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5427    3.7366   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212   -1.2496   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5282    2.6824   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4060    2.9711    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0634    1.6251   -0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5653    0.6233    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2885    0.8704   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7198   -2.2037    0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0982   -4.1157    0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7098   -3.7156    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 16  1  0
 16 17  1  0
 17 27  2  0
 27 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 18  2  0
 13 14  1  0
 14 15  2  0
 10  3  1  0
 27 12  1  0
 19 25  1  0
 14  9  1  0
 18 17  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  4 33  1  0
  8 34  1  0
  8 35  1  0
 11 36  1  0
 16 37  1  0
 16 38  1  0
 24 44  1  0
 23 43  1  0
 22 42  1  0
 21 40  1  0
 21 41  1  0
 18 39  1  0
M  END


  Mrv1652305302218442D          

 27 31  0  0  0  0            999 V2000
    5.4176   -1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9255   -1.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6165   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9168   -0.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9755   -0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784    0.5840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1264    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    1.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929    1.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255    1.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8804    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284    0.0694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046    1.9817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    2.4233    0.0000 O   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 15 25  1  0  0  0  0
 13 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC=C(N)C1=C3)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3

> <INCHI_KEY>
FUXVKZWTXQUGMW-UHFFFAOYSA-N

> <FORMULA>
C20H17N3O4

> <MOLECULAR_WEIGHT>
363.373

> <EXACT_MASS>
363.121906039

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.8635704839629

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

> <JCHEM_LOGP>
0.391317284

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.710530193261718

> <JCHEM_PKA_STRONGEST_BASIC>
3.9144057675558748

> <JCHEM_POLAR_SURFACE_AREA>
105.75000000000001

> <JCHEM_REFRACTIVITY>
99.19290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-22         0                                  
HETATM    1  C   UNK     0      10.113  -3.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.061  -2.122   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.484  -0.695   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.178  -1.511   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.990  -0.374   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.021  -1.519   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.466   1.090   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.436   2.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.930   1.914   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.454   0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.947   0.130   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.917   1.274   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       7.393   2.739   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.147   3.644   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.901   2.739   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.377   1.274   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.346   0.130   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.173   1.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       0.382   3.699   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.395   3.059   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.899   3.059   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.375   4.524   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   10                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18   25                                                  
CONECT   25   24   15                                                       
CONECT   26   13    9   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₇N₃O₄

Average Mass

363.3730 Da

Monoisotopic Mass

363.12191 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC=C(N)C1=C3)C2=O

InChI Identifier

InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3

InChI Key

FUXVKZWTXQUGMW-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Camptothecins

Sub Class

Not Available

Direct Parent

Camptothecins

Alternative Parents

Substituents

Camptothecin
Aminoquinoline
Pyranopyridine
Quinoline
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Lactam
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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

External Links

HMDB ID

HMDB0247579

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

115975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rubitecan

METLIN ID

Not Available

PubChem Compound

131182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Prijovich ZM, Burnouf PA, Chou HC, Huang PT, Chen KC, Cheng TL, Leu YL, Roffler SR: Synthesis and Antitumor Properties of BQC-Glucuronide, a Camptothecin Prodrug for Selective Tumor Activation. Mol Pharm. 2016 Apr 4;13(4):1242-50. doi: 10.1021/acs.molpharmaceut.5b00771. Epub 2016 Mar 8. [PubMed:26824303 ]
Su YC, Cheng TC, Leu YL, Roffler SR, Wang JY, Chuang CH, Kao CH, Chen KC, Wang HE, Cheng TL: PET imaging of beta-glucuronidase activity by an activity-based 124I-trapping probe for the personalized glucuronide prodrug targeted therapy. Mol Cancer Ther. 2014 Dec;13(12):2852-63. doi: 10.1158/1535-7163.MCT-14-0212. Epub 2014 Oct 2. [PubMed:25277385 ]
Maier-Salamon A, Thalhammer T, Reznicek G, Bohmdorfer M, Zupko I, Hartl A, Jaeger W: Cytochrome P450 3A-mediated metabolism of the topoisomerase I inhibitor 9-aminocamptothecin: impact on cancer therapy. Int J Oncol. 2014 Aug;45(2):877-86. doi: 10.3892/ijo.2014.2473. Epub 2014 May 29. [PubMed:24889073 ]
Rahman S, Patel D, Savva M: Physicochemical characterization of 9-aminocamptothecin in aqueous solutions. AAPS PharmSciTech. 2014 Feb;15(1):223-9. doi: 10.1208/s12249-013-0046-y. Epub 2013 Dec 3. [PubMed:24297599 ]
Patel D, Rahman S, Savva M: Kinetic and thermodynamic studies of 9-aminocamptothecin hydrolysis at physiological pH in the presence of human serum albumin. Eur J Pharm Sci. 2013 Aug 16;49(5):858-63. doi: 10.1016/j.ejps.2013.06.005. Epub 2013 Jun 19. [PubMed:23791639 ]

Showing NP-Card for 9-Aminocamptothecin (NP0137176)

MOL for NP0137176 (9-Aminocamptothecin)

3D MOL for NP0137176 (9-Aminocamptothecin)

3D SDF for NP0137176 (9-Aminocamptothecin)

3D-SDF for NP0137176 (9-Aminocamptothecin)

PDB for NP0137176 (9-Aminocamptothecin)

3D PDB for NP0137176 (9-Aminocamptothecin)

SMILES for NP0137176 (9-Aminocamptothecin)

INCHI for NP0137176 (9-Aminocamptothecin)

Structure for NP0137176 (9-Aminocamptothecin)

3D Structure for NP0137176 (9-Aminocamptothecin)