NP-MRD: Showing NP-Card for (1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate (NP0149463)

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Record Information

Version

2.0

Created at

2022-09-02 05:21:31 UTC

Updated at

2022-09-02 05:21:31 UTC

NP-MRD ID

NP0149463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate

Description

MAYTANSINE, also known as soravtansine or dmmo-maytansine, 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. (1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate is found in Gymnosporia diversifolia. (1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate was first documented in 2021 (PMID: 34461087). Based on a literature review a significant number of articles have been published on MAYTANSINE (PMID: 35594923) (PMID: 35373789) (PMID: 35362385) (PMID: 35316825) (PMID: 35161302) (PMID: 35064993).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207212D          

 48 51  0  0  1  0            999 V2000
    2.5979   -4.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8654   -2.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2817   -1.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -0.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8760   -1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992   -1.7291    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3679   -0.6713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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  8  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
 34 40  1  0
  4  5  1  0
 29 26  1  0
 39 32  1  0
 42 84  1  0
 42 85  1  0
 42 86  1  0
 40 83  1  1
 43 87  1  0
 44 88  1  0
 45 89  1  0
 47 90  1  0
 47 91  1  0
 47 92  1  0
 48 93  1  0
 48 94  1  0
  6 53  1  0
 11 54  1  0
 11 55  1  0
 11 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  1
 19 60  1  1
 20 61  1  0
 20 62  1  0
 20 63  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 24 67  1  0
 24 68  1  0
 24 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  1
 30 74  1  1
 31 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  6
 33 79  1  0
 33 80  1  0
 35 81  1  0
 38 82  1  0
  1 49  1  0
  1 50  1  0
  1 51  1  0
  4 52  1  0
M  END


  Mrv1652309022207212D          

 48 51  0  0  1  0            999 V2000
    2.5979   -4.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -3.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -2.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2817   -1.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -0.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8760   -1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -1.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992   -1.7291    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3679   -0.6713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -0.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328    0.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -0.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8140    0.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1140    1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285    1.6843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430    1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430    0.4468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    1.6843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2575    2.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719    1.2718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719    0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6864    1.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4009    1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6864    2.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958    2.0940    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9184    2.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385    2.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634    2.6238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0947    3.3682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5171    4.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    3.3382    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0629    2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    2.2579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4877    1.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420    2.8221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1695    3.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813    4.1890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761    3.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7527    1.4237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5099    1.0964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1336    0.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0991    0.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663   -0.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780   -1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -1.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606   -1.3773    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 29 28  1  1  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 34 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
  5 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1\C=C\C=C(C)\CC2=CC(N(C)C(=O)CC(OC(=O)[C@H](C)N(C)C(C)=O)[C@]3(C)O[C@H]3[C@H](C)[C@@H]3C[C@@]1(O)N=C(O)O3)=C(Cl)C(OC)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11+/t19-,20+,25+,26-,27?,30+,33+,34+/m1/s1

> <INCHI_KEY>
WKPWGQKGSOKKOO-QVMUNQMUSA-N

> <FORMULA>
C34H46ClN3O10

> <MOLECULAR_WEIGHT>
692.2

> <EXACT_MASS>
691.2871724

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
70.06586784214468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3S,5S,16E,18E,20R,21S)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^{10,14}.0^{3,5}]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2S)-2-(N-methylacetamido)propanoate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.8128033696666632

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.719515679180244

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7486688745730805

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8728430845822293

> <JCHEM_POLAR_SURFACE_AREA>
159.95999999999998

> <JCHEM_REFRACTIVITY>
176.944

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,5S,16E,18E,20R,21S)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^{10,14}.0^{3,5}]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2S)-2-(N-methylacetamido)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.849  -7.489   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.747  -6.415   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.126  -4.922   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.349  -4.019   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.259  -2.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.996  -1.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.369  -2.453   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.533  -3.650   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       2.052  -3.228   0.000  0.00  0.00          Cl+0
HETATM   10  N   UNK     0       6.287  -1.253   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.825  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.475   0.078   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.026  -0.446   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.253   1.580   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.946   2.374   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.280   3.144   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.614   2.374   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.614   0.834   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.947   3.144   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.947   4.684   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       9.281   2.374   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       9.281   0.834   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.615   3.144   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.948   2.374   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.615   4.684   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.912   3.909   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.448   3.792   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.179   5.426   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.732   4.898   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.043   6.287   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.832   7.610   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.475   6.231   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.117   4.713   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.358   4.215   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.777   3.617   0.000  0.00  0.00           O+0
HETATM   36  N   UNK     0      -2.505   5.268   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      -2.183   6.786   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.325   7.820   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -0.702   7.259   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.405   2.658   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.819   2.047   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.996   0.517   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.249   1.634   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.185   0.105   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.057  -0.793   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.266  -2.298   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.151  -3.361   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.726  -2.571   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   48                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   15   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   26   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36   40                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   34   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46    5                                                       
MASTER        0    0    0    0    0    0    0    0   48    0  102    0
END

View in JSmol

Synonyms

Value	Source
DMMO-maytansine	MeSH
Maytansinoid DM1	MeSH
N2'-Deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)maytansine	MeSH
Soravtansine	MeSH
DM4, Maytansinoid	MeSH
Emtansine	MeSH
DM1, Maytansinoid	MeSH
Maitansine	MeSH
Maytansinoid DM4	MeSH
Mertansine	MeSH
DMMO maytansine	MeSH
Ravtansine	MeSH

Chemical Formula

C₃₄H₄₆ClN₃O₁₀

Average Mass

692.2000 Da

Monoisotopic Mass

691.28717 Da

IUPAC Name

(1S,2R,3S,5S,16E,18E,20R,21S)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^{10,14}.0^{3,5}]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2S)-2-(N-methylacetamido)propanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1\C=C\C=C(C)\CC2=CC(N(C)C(=O)CC(OC(=O)[C@H](C)N(C)C(C)=O)[C@]3(C)O[C@H]3[C@H](C)[C@@H]3C[C@@]1(O)N=C(O)O3)=C(Cl)C(OC)=C2

InChI Identifier

InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11+/t19-,20+,25+,26-,27?,30+,33+,34+/m1/s1

InChI Key

WKPWGQKGSOKKOO-QVMUNQMUSA-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
Maytenus diversifolia	LOTUS Database	35616633

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
Alpha-amino acid ester
Alanine or derivatives
Alpha-amino acid or derivatives
Anisole
Phenol ether
Alkyl aryl ether
1,3-oxazinane
Oxazinane
Aryl chloride
Benzenoid
Aryl halide
Tertiary carboxylic acid amide
Carbamic acid ester
Acetamide
Carboxylic acid ester
Carboxamide group
Lactam
Alkanolamine
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organochloride
Organohalogen compound
Organic oxide
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
logP	3.18	ALOGPS
logP	3.81	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	159.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	176.94 m³·mol⁻¹	ChemAxon
Polarizability	70.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002351

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101529024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bai R, Smith AB 3rd, Pettit GR, Hamel E: The interaction of spongistatin 1 with tubulin. Arch Biochem Biophys. 2022 Sep 30;727:109296. doi: 10.1016/j.abb.2022.109296. Epub 2022 May 17. [PubMed:35594923 ]
Eren E, Watts NR, Sackett DL, Wingfield PT: Conformational changes in tubulin upon binding cryptophycin-52 reveal its mechanism of action. J Biol Chem. 2021 Oct;297(4):101138. doi: 10.1016/j.jbc.2021.101138. Epub 2021 Aug 28. [PubMed:34461087 ]
Xie HN, Chen YY, Zhu GB, Han HH, Hu XL, Pan ZQ, Zang Y, Xie DH, He XP, Li J, James TD: Targeted delivery of maytansine to liver cancer cells via galactose-modified supramolecular two-dimensional glycomaterial. Chem Commun (Camb). 2022 Apr 19;58(32):5029-5032. doi: 10.1039/d1cc06809a. [PubMed:35373789 ]
Pathak K, Pathak MP, Saikia R, Gogoi U, Sahariah JJ, Zothantluanga JH, Samanta A, Das A: Cancer Chemotherapy via Natural Bioactive Compounds. Curr Drug Discov Technol. 2022;19(4):e310322202888. doi: 10.2174/1570163819666220331095744. [PubMed:35362385 ]
Cheng H, Xiong G, Li Y, Zhu J, Xiong X, Wang Q, Zhang L, Dong H, Zhu C, Liu G, Chen H: Increased yield of AP-3 by inactivation of asm25 in Actinosynnema pretiosum ssp. auranticum ATCC 31565. PLoS One. 2022 Mar 22;17(3):e0265517. doi: 10.1371/journal.pone.0265517. eCollection 2022. [PubMed:35316825 ]
Pitakbut T, Spiteller M, Kayser O: Genome Mining and Gene Expression Reveal Maytansine Biosynthetic Genes from Endophytic Communities Living inside Gymnosporia heterophylla (Eckl. and Zeyh.) Loes. and the Relationship with the Plant Biosynthetic Gene, Friedelin Synthase. Plants (Basel). 2022 Jan 25;11(3):321. doi: 10.3390/plants11030321. [PubMed:35161302 ]
Ma W, Yang Y, Zhu J, Jia W, Zhang T, Liu Z, Chen X, Lin Y: Biomimetic Nanoerythrosome-Coated Aptamer-DNA Tetrahedron/Maytansine Conjugates: pH-Responsive and Targeted Cytotoxicity for HER2-Positive Breast Cancer. Adv Mater. 2022 Nov;34(46):e2109609. doi: 10.1002/adma.202109609. Epub 2022 Feb 17. [PubMed:35064993 ]
Marzullo P, Boiarska Z, Perez-Pena H, Abel AC, Alvarez-Bernad B, Lucena-Agell D, Vasile F, Sironi M, Altmann KH, Prota AE, Diaz JF, Pieraccini S, Passarella D: Maytansinol Derivatives: Side Reactions as a Chance for New Tubulin Binders. Chemistry. 2022 Jan 10;28(2):e202103520. doi: 10.1002/chem.202103520. Epub 2021 Nov 29. [PubMed:34788896 ]
Cho N, Ko S, Shokeen M: Tissue biodistribution and tumor targeting of near-infrared labelled anti-CD38 antibody-drug conjugate in preclinical multiple myeloma. Oncotarget. 2021 Sep 28;12(20):2039-2050. doi: 10.18632/oncotarget.28074. eCollection 2021 Sep 28. [PubMed:34611478 ]
Huang YY, Chen L, Ma GX, Xu XD, Jia XG, Deng FS, Li XJ, Yuan JQ: A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies. Molecules. 2021 Jul 28;26(15):4563. doi: 10.3390/molecules26154563. [PubMed:34361712 ]
Kollmannsberger C, Britten CD, Olszanski AJ, Walker JA, Zang W, Willard MD, Radtke DB, Farrington DL, Bell-McGuinn KM, Patnaik A: A phase 1 study of LY3076226, a fibroblast growth factor receptor 3 (FGFR3) antibody-drug conjugate, in patients with advanced or metastatic cancer. Invest New Drugs. 2021 Dec;39(6):1613-1623. doi: 10.1007/s10637-021-01146-x. Epub 2021 Jul 15. [PubMed:34264412 ]
Li W, Huang M, Li Y, Xia A, Tan L, Zhang Z, Wang Y, Yang J: C3 ester side chain plays a pivotal role in the antitumor activity of Maytansinoids. Biochem Biophys Res Commun. 2021 Aug 20;566:197-203. doi: 10.1016/j.bbrc.2021.05.071. Epub 2021 Jun 15. [PubMed:34144258 ]
Anderson MG, Zhang Q, Rodriguez LE, Hecquet CM, Donawho CK, Ansell PJ, Reilly EB: ABBV-176, a PRLR antibody drug conjugate with a potent DNA-damaging PBD cytotoxin and enhanced activity with PARP inhibition. BMC Cancer. 2021 Jun 9;21(1):681. doi: 10.1186/s12885-021-08403-5. [PubMed:34107902 ]
Lombardi J, Lory P, Martin N, Mayeur D, Combret S, Grandvuillemin A, Boulay C, Schmitt A: Trastuzumab-emtansine induced pleural and pericardial effusions. J Oncol Pharm Pract. 2021 Dec;27(8):2041-2044. doi: 10.1177/10781552211015772. Epub 2021 May 18. [PubMed:34000917 ]
Tang SC, Capra CL, Ajebo GH, Meza-Junco J, Mairs S, Craft BS, Zhu X, Maihle N, Hillegass WB: Systemic toxicities of trastuzumab-emtansine predict tumor response in HER2+ metastatic breast cancer. Int J Cancer. 2021 Apr 12;149(4):909-16. doi: 10.1002/ijc.33597. [PubMed:33844843 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate (NP0149463)

MOL for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

3D MOL for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

3D SDF for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

3D-SDF for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

PDB for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

3D PDB for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

SMILES for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

INCHI for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

Structure for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)

3D Structure for NP0149463 ((1s,2r,3s,5s,16e,18e,20r,21s)-11-chloro-21,23-dihydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8-oxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1¹⁰,¹⁴.0³,⁵]hexacosa-10,12,14(26),16,18,22-hexaen-6-yl (2s)-2-(n-methylacetamido)propanoate)