NP-MRD: Showing NP-Card for 22-Demethylmaytansinol 3-isobutyrate (NP0062128)

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Record Information

Version

2.0

Created at

2022-04-28 06:47:26 UTC

Updated at

2022-04-28 06:47:26 UTC

NP-MRD ID

NP0062128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-Demethylmaytansinol 3-isobutyrate

Description

22-Demethylmaytansinol 3-isobutyrate is found in Streptomyces castaneus IFO 13670.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208472D          

 43 46  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282208472D          

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   10.9183    3.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0838    2.1265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5225    2.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9028    1.0116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4206    0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5995    0.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7615   -0.4225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447    1.7496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7706   -1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1942   -2.2136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0412   -2.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4070   -2.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9768   -3.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7784   -2.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7449   -3.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3146   -4.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9433   -4.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6017   -1.2736    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5834    0.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0697    0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  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
  2 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 25  1  6  0  0  0
 25 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 15 30  1  0  0  0  0
 17 31  1  6  0  0  0
 14 32  1  1  0  0  0
 13 33  1  6  0  0  0
 12 33  1  0  0  0  0
 12 34  1  6  0  0  0
 11 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
  5 41  1  0  0  0  0
  4 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062128

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H41ClN2O9/c1-16(2)28(36)42-24-14-25(35)33-20-12-19(13-21(39-6)26(20)32)11-17(3)9-8-10-23(40-7)31(38)15-22(41-29(37)34-31)18(4)27-30(24,5)43-27/h8-10,12-13,16,18,22-24,27,38H,11,14-15H2,1-7H3,(H,33,35)(H,34,37)/b10-8+,17-9-/t18-,22-,23+,24-,27-,30+,31-/m0/s1

> <INCHI_KEY>
BOYNDXJJKZMFBK-DZFAXLMPSA-N

> <FORMULA>
C31H41ClN2O9

> <MOLECULAR_WEIGHT>
621.12

> <EXACT_MASS>
620.2500586

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.683451913806984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,5R,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^{10,14}.0^{3,5}]hexacosa-10,12,14(26),16,18-pentaen-6-yl 2-methylpropanoate

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
4.718564897666664

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.677011569623346

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.354229682924467

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7417498386781625

> <JCHEM_POLAR_SURFACE_AREA>
144.95000000000002

> <JCHEM_REFRACTIVITY>
160.04480000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,5R,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^{10,14}.0^{3,5}]hexacosa-10,12,14(26),16,18-pentaen-6-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      22.465   0.676   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.541   1.974   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.984   1.672   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.412   0.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.379  -0.955   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.925  -0.789   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      21.897  -2.391   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      20.987  -3.702   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      21.819  -4.999   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      19.433  -3.980   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.993  -3.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.443  -3.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.979  -2.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.442  -2.150   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.307  -0.988   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.167   0.318   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.579   1.769   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.943   2.608   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.392   3.258   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.837   3.968   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.329   4.500   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.920   4.512   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.225   3.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.381   5.981   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.223   3.969   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.042   5.274   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      11.019   1.888   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      10.118   0.625   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.586   0.776   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.755  -0.789   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      12.217   3.266   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.639  -3.465   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.296  -4.132   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.877  -4.582   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      17.560  -4.831   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      18.623  -5.945   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      20.120  -5.581   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      18.190  -7.423   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.254  -8.537   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.694  -7.787   0.000  0.00  0.00           C+0
HETATM   41 Cl   UNK     0      19.790  -2.377   0.000  0.00  0.00          Cl+0
HETATM   42  O   UNK     0      17.889   0.018   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      16.930   1.223   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   42                                                  
CONECT    5    4    6   41                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13   33   34                                             
CONECT   13   12   14   33                                                  
CONECT   14   13   15   32                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27   31                                             
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22    2                                                       
CONECT   24   22                                                            
CONECT   25   18   26                                                       
CONECT   26   25                                                            
CONECT   27   17   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   15                                                       
CONECT   31   17                                                            
CONECT   32   14                                                            
CONECT   33   13   12                                                       
CONECT   34   12                                                            
CONECT   35   11   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41    5                                                            
CONECT   42    4   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₁ClN₂O₉

Average Mass

621.1200 Da

Monoisotopic Mass

620.25006 Da

IUPAC Name

(1S,2S,3S,5R,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,16-trimethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1^{10,14}.0^{3,5}]hexacosa-10,12,14(26),16,18-pentaen-6-yl 2-methylpropanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H41ClN2O9/c1-16(2)28(36)42-24-14-25(35)33-20-12-19(13-21(39-6)26(20)32)11-17(3)9-8-10-23(40-7)31(38)15-22(41-29(37)34-31)18(4)27-30(24,5)43-27/h8-10,12-13,16,18,22-24,27,38H,11,14-15H2,1-7H3,(H,33,35)(H,34,37)/b10-8+,17-9-/t18-,22-,23+,24-,27-,30+,31-/m0/s1

InChI Key

BOYNDXJJKZMFBK-DZFAXLMPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 castaneus IFO 13670	Bacteria	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	3.24	ALOGPS
logP	4.72	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	11.35	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	144.95 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	160.04 m³·mol⁻¹	ChemAxon
Polarizability	62.68 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	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for 22-Demethylmaytansinol 3-isobutyrate (NP0062128)

MOL for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

3D MOL for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

3D SDF for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

3D-SDF for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

PDB for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

3D PDB for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

SMILES for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

INCHI for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

Structure for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)

3D Structure for NP0062128 (22-Demethylmaytansinol 3-isobutyrate)