NP-MRD: Showing NP-Card for Salinosporamide A (NP0004529)

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Record Information

Version

2.0

Created at

2020-12-09 02:00:02 UTC

Updated at

2021-07-15 16:49:26 UTC

NP-MRD ID

NP0004529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Salinosporamide A

Provided By

NPAtlas

Description

Marizomib is also known as ML 858 or npi 0052. Salinosporamide A is found in Salinispora and Salinispora tropica. Salinosporamide A was first documented in 2003 (PMID: 12548698). Based on a literature review a small amount of articles have been published on Marizomib (PMID: 15916417) (PMID: 17121896) (PMID: 17497868) (PMID: 17609425).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118073D          

 41 43  0  0  0  0            999 V2000
    1.6643    1.7699   -1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    0.7406   -0.0171 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6873    1.2627    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159    0.1936    1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764   -0.3977    2.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    0.1000    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8990    0.8739    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4082    1.0299   -1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    0.2756    1.1772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2489   -1.1329    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128   -1.3665    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043   -0.3487   -0.6781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9661    1.0096   -0.0810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1524    1.1527    1.1632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3850   -1.2397   -0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -1.6243   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -2.7987    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839   -0.4065   -0.3206 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7194   -0.3346    0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7518   -1.4150    0.4868 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4893   -1.3554   -1.1208 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.2815   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    2.3793   -0.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8361    2.4846   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474    1.9170    0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733    0.3316   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587    0.2937    2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.9353    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512   -2.4215   -0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -0.3275   -1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663   -0.7369   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222    1.7551   -0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    1.3176    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.9706    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889    2.1994    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -1.8310   -0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -0.3313   -1.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970   -0.3807    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2077    0.6760    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -2.4162    0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646   -1.2147    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
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 18 19  1  0  0  0  0
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 20 41  1  0  0  0  0
M  END

     RDKit          3D

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    1.6643    1.7699   -1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    0.7406   -0.0171 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6873    1.2627    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159    0.1936    1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764   -0.3977    2.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    0.1000    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8990    0.8739    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4082    1.0299   -1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    0.2756    1.1772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2489   -1.1329    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128   -1.3665    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043   -0.3487   -0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9661    1.0096   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524    1.1527    1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -1.2397   -0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -1.6243   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -2.7987    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839   -0.4065   -0.3206 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7194   -0.3346    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7518   -1.4150    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -1.3554   -1.1208 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.2815   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    2.3793   -0.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4512   -2.4215   -0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -0.3275   -1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663   -0.7369   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222    1.7551   -0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    1.3176    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.9706    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889    2.1994    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -1.8310   -0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -0.3313   -1.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970   -0.3807    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2077    0.6760    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -2.4162    0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646   -1.2147    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  4  1  1
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
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 16 17  2  0
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  6  2  1  0
 14  9  1  0
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  1 23  1  0
  1 24  1  0
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M  END


  Mrv1652306242118073D          

 41 43  0  0  0  0            999 V2000
    1.6643    1.7699   -1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    0.7406   -0.0171 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6873    1.2627    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159    0.1936    1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764   -0.3977    2.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    0.1000    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8990    0.8739    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4082    1.0299   -1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    0.2756    1.1772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2489   -1.1329    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128   -1.3665    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043   -0.3487   -0.6781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9661    1.0096   -0.0810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1524    1.1527    1.1632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3850   -1.2397   -0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -1.6243   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -2.7987    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839   -0.4065   -0.3206 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7194   -0.3346    0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7518   -1.4150    0.4868 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4893   -1.3554   -1.1208 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.2815   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    2.3793   -0.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0049    1.3176    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.9706    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 14  9  1  0  0  0  0
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  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  7 25  1  1  0  0  0
  8 26  1  0  0  0  0
  9 27  1  1  0  0  0
 10 28  1  0  0  0  0
 11 29  1  0  0  0  0
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 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 15 36  1  0  0  0  0
 18 37  1  6  0  0  0
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 20 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])([C@]1([H])C([H])=C([H])C([H])([H])C([H])([H])C1([H])[H])[C@@]12N([H])C(=O)[C@]([H])(C([H])([H])C([H])([H])Cl)[C@@]1(OC2=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1

> <INCHI_KEY>
NGWSFRIPKNWYAO-SHTIJGAHSA-N

> <FORMULA>
C15H20ClNO4

> <MOLECULAR_WEIGHT>
313.78

> <EXACT_MASS>
313.1080858

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.144602621799965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-[(1S)-cyclohex-2-en-1-yl](hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.2398347273333343

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.725089535119388

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.317678551607937

> <JCHEM_PKA_STRONGEST_BASIC>
-2.164533496620975

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
77.3853

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salinosporamide A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    1.6643    1.7699   -1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    0.7406   -0.0171 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6873    1.2627    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159    0.1936    1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764   -0.3977    2.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    0.1000    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8990    0.8739    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4082    1.0299   -1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    0.2756    1.1772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2489   -1.1329    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128   -1.3665    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043   -0.3487   -0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9661    1.0096   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524    1.1527    1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -1.2397   -0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -1.6243   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -2.7987    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839   -0.4065   -0.3206 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7194   -0.3346    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7518   -1.4150    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -1.3554   -1.1208 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.2815   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    2.3793   -0.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8361    2.4846   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474    1.9170    0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733    0.3316   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587    0.2937    2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.9353    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512   -2.4215   -0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -0.3275   -1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663   -0.7369   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222    1.7551   -0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    1.3176    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.9706    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889    2.1994    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -1.8310   -0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -0.3313   -1.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970   -0.3807    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2077    0.6760    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -2.4162    0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646   -1.2147    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  4  1  1
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6  2  1  0
 14  9  1  0
 18  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  7 25  1  1
  8 26  1  0
  9 27  1  1
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  6
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.664   1.770  -1.117  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.647   0.741  -0.017  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.687   1.263   1.274  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.916   0.194   1.704  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.776  -0.398   2.793  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.363   0.100   0.303  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.899   0.874   0.239  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.408   1.030  -1.044  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.918   0.276   1.177  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.249  -1.133   0.873  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.213  -1.367   0.016  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.004  -0.349  -0.678  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.966   1.010  -0.081  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.152   1.153   1.163  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.385  -1.240  -0.213  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.781  -1.624  -0.141  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.171  -2.799   0.041  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.584  -0.407  -0.321  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.719  -0.335   0.665  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.752  -1.415   0.487  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       5.489  -1.355  -1.121  0.00  0.00          Cl+0
HETATM   22  H   UNK     0       1.789   1.282  -2.087  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.601   2.379  -0.957  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.836   2.485  -1.072  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.647   1.917   0.596  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.073   0.332  -1.652  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.559   0.294   2.239  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.708  -1.935   1.361  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.451  -2.422  -0.205  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.683  -0.328  -1.742  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.066  -0.737  -0.733  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.622   1.755  -0.855  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.005   1.318   0.163  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.745   0.971   2.083  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.789   2.199   1.231  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.378  -1.831  -0.569  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.953  -0.331  -1.368  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.297  -0.381   1.697  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.208   0.676   0.606  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.353  -2.416   0.659  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.565  -1.215   1.240  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3    6   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15    2                                             
CONECT    7    6    8    9   25                                             
CONECT    8    7   26                                                       
CONECT    9    7   10   14   27                                             
CONECT   10    9   11   28                                                  
CONECT   11   10   12   29                                                  
CONECT   12   11   13   30   31                                             
CONECT   13   12   14   32   33                                             
CONECT   14   13    9   34   35                                             
CONECT   15    6   16   36                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19    2   37                                             
CONECT   19   18   20   38   39                                             
CONECT   20   19   21   40   41                                             
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    7                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   20                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    1.6643    1.7699   -1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    0.7406   -0.0171 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6873    1.2627    1.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159    0.1936    1.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7764   -0.3977    2.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    0.1000    0.3030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8990    0.8739    0.2392 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4082    1.0299   -1.0436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    0.2756    1.1772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2489   -1.1329    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128   -1.3665    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0043   -0.3487   -0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9661    1.0096   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524    1.1527    1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -1.2397   -0.2125 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -1.6243   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -2.7987    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5839   -0.4065   -0.3206 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7194   -0.3346    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7518   -1.4150    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -1.3554   -1.1208 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.2815   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    2.3793   -0.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8361    2.4846   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474    1.9170    0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733    0.3316   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587    0.2937    2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.9353    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512   -2.4215   -0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -0.3275   -1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0663   -0.7369   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222    1.7551   -0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049    1.3176    0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.9706    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889    2.1994    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -1.8310   -0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9526   -0.3313   -1.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970   -0.3807    1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2077    0.6760    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -2.4162    0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646   -1.2147    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  4  1  1
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6  2  1  0
 14  9  1  0
 18  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  7 25  1  1
  8 26  1  0
  9 27  1  1
 10 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  6
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Salinosporamide a	ChEBI
Marizomibum	ChEBI
ML 858	ChEBI
NPI 0052	ChEBI
NPI-0052	ChEBI
Marizomib	ChEBI
NPI-0052Salinisporamide a	ChEMBL
Homosalinosporamide a	MeSH
Salinosporamide a	MeSH

Chemical Formula

C₁₅H₂₀ClNO₄

Average Mass

313.7800 Da

Monoisotopic Mass

313.10809 Da

IUPAC Name

(1R,4R,5S)-4-(2-chloroethyl)-1-[(S)-[(1S)-cyclohex-2-en-1-yl](hydroxy)methyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

Traditional Name

salinosporamide A

CAS Registry Number

Not Available

SMILES

C[C@@]12OC(=O)[C@@]1(NC(=O)[C@@H]2CCCl)[C@@H](O)[C@H]1CCCC=C1

InChI Identifier

InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1

InChI Key

NGWSFRIPKNWYAO-SHTIJGAHSA-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
Salinispora	NPAtlas	12548698
Salinispora tropica	-	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Oxoproline
Para-oxazepine
2-pyrrolidone
Pyrrolidone
Beta_propiolactone
Pyrrolidine
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Oxetane
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organohalogen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Alkyl halide
Organochloride
Organonitrogen compound
Organooxygen compound
Alkyl chloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:48045 )
organic heterobicyclic compound (CHEBI:48045 )
beta-lactone (CHEBI:48045 )
gamma-lactam (CHEBI:48045 )
salinosporamide (CHEBI:48045 )

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	1.39	ALOGPS
logP	1.24	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.32	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.39 m³·mol⁻¹	ChemAxon
Polarizability	31.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011013

HMDB ID

Not Available

DrugBank ID

DB11762

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040190

Chemspider ID

9522473

KEGG Compound ID

Not Available

BioCyc ID

CPD-12674

BiGG ID

Not Available

Wikipedia Link

Salinosporamide_A

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

48045

Good Scents ID

Not Available

References

General References

Feling RH, Buchanan GO, Mincer TJ, Kauffman CA, Jensen PR, Fenical W: Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora. Angew Chem Int Ed Engl. 2003 Jan 20;42(3):355-7. doi: 10.1002/anie.200390115. [PubMed:12548698 ]
Macherla VR, Mitchell SS, Manam RR, Reed KA, Chao TH, Nicholson B, Deyanat-Yazdi G, Mai B, Jensen PR, Fenical WF, Neuteboom ST, Lam KS, Palladino MA, Potts BC: Structure-activity relationship studies of salinosporamide A (NPI-0052), a novel marine derived proteasome inhibitor. J Med Chem. 2005 Jun 2;48(11):3684-7. doi: 10.1021/jm048995+. [PubMed:15916417 ]
Cusack JC Jr, Liu R, Xia L, Chao TH, Pien C, Niu W, Palombella VJ, Neuteboom ST, Palladino MA: NPI-0052 enhances tumoricidal response to conventional cancer therapy in a colon cancer model. Clin Cancer Res. 2006 Nov 15;12(22):6758-64. doi: 10.1158/1078-0432.CCR-06-1151. [PubMed:17121896 ]
Ling T, Macherla VR, Manam RR, McArthur KA, Potts BC: Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052). Org Lett. 2007 Jun 7;9(12):2289-92. doi: 10.1021/ol0706051. Epub 2007 May 12. [PubMed:17497868 ]
Ahn KS, Sethi G, Chao TH, Neuteboom ST, Chaturvedi MM, Palladino MA, Younes A, Aggarwal BB: Salinosporamide A (NPI-0052) potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through down-modulation of NF-kappaB regulated gene products. Blood. 2007 Oct 1;110(7):2286-95. doi: 10.1182/blood-2007-04-084996. Epub 2007 Jul 3. [PubMed:17609425 ]

Showing NP-Card for Salinosporamide A (NP0004529)

MOL for NP0004529 (Salinosporamide A)

3D MOL for NP0004529 (Salinosporamide A)

3D SDF for NP0004529 (Salinosporamide A)

3D-SDF for NP0004529 (Salinosporamide A)

PDB for NP0004529 (Salinosporamide A)

3D PDB for NP0004529 (Salinosporamide A)

SMILES for NP0004529 (Salinosporamide A)

INCHI for NP0004529 (Salinosporamide A)

Structure for NP0004529 (Salinosporamide A)

3D Structure for NP0004529 (Salinosporamide A)