NP-MRD: Showing NP-Card for WS 009 B (NP0004758)

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Record Information

Version

1.0

Created at

2020-12-09 02:10:48 UTC

Updated at

2021-07-15 16:50:05 UTC

NP-MRD ID

NP0004758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

WS 009 B

Provided By

NPAtlas

Description

3-[(4A,6,8,12a,12b-pentahydroxy-3-methyl-1,7,12-trioxo-1,4,4a,5,6,6a,7,12,12a,12b-decahydrotetraphen-6a-yl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. WS 009 B is found in Streptomyces sp. It was first documented in 1992 (PMID: 1325433). Based on a literature review very few articles have been published on 3-[(4a,6,8,12a,12b-pentahydroxy-3-methyl-1,7,12-trioxo-1,4,4a,5,6,6a,7,12,12a,12b-decahydrotetraphen-6a-yl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid (PMID: 26389497) (PMID: 26389486) (PMID: 26389480) (PMID: 26389479).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 62 65  0  0  0  0            999 V2000
    5.6030    1.3283    2.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9227    1.3050    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030    2.4085    0.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215    0.0889    0.2222 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    0.0604   -1.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4493   -0.5271   -0.8451 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6317    0.5669    0.3096 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    0.0151    0.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.2213   -1.6766   -3.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242118093D          

 62 65  0  0  0  0            999 V2000
    5.6030    1.3283    2.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9227    1.3050    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5554   -1.5011   -2.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995   -0.0559   -0.5123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2787    0.8232   -1.4444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377    0.3418   -0.4165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0831   -0.8681   -0.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0368    3.1001   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042    4.5916   -0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    2.5665    0.6488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7847    1.0907    0.7851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0923    0.6631    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    0.7967    2.0253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5417    1.0374    1.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1921    0.8240    2.9133 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5989   -0.6954   -2.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6942   -1.2418   -1.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1100   -0.8258   -3.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493    2.0177    2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8744    1.6340    2.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9215    0.2935    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218   -0.7980    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    1.1197   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -1.5489   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -0.4968   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951   -4.3778    3.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543   -5.6812    1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -5.8006   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237   -3.7523   -1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5004    0.5337   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1828   -1.2265    0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1190    2.8548   -2.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7097    4.9917   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    5.1065    0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3684    4.6879   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656    3.0947    1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7103    2.9833    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7703    1.3010    0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0940   -0.2452    2.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    1.4840    2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608    2.0161    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249    1.6081    3.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2213   -1.6766   -3.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 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  0  0  0  0
 33 34  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 20  8  1  0  0  0  0
 30 22  1  0  0  0  0
 33  8  1  0  0  0  0
 17 11  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  6  0  0  0
  6 43  1  0  0  0  0
  6 44  1  0  0  0  0
 13 45  1  0  0  0  0
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 15 47  1  0  0  0  0
 16 48  1  0  0  0  0
 21 49  1  0  0  0  0
 23 50  1  0  0  0  0
 26 51  1  0  0  0  0
 28 52  1  0  0  0  0
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 29 56  1  0  0  0  0
 31 57  1  0  0  0  0
 32 58  1  0  0  0  0
 32 59  1  0  0  0  0
 33 60  1  6  0  0  0
 34 61  1  0  0  0  0
 37 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(N([H])C(=O)C([H])([H])[H])C([H])([H])S[C@]12C(=O)C3=C(O[H])C([H])=C([H])C([H])=C3C(=O)[C@@]1(O[H])[C@]1(O[H])C(=O)C([H])=C(C([H])([H])[H])C([H])([H])[C@]1(O[H])C([H])([H])[C@@]2([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H25NO11S/c1-10-6-15(28)23(35)21(34,7-10)8-16(29)22(37-9-13(20(32)33)25-11(2)26)19(31)17-12(4-3-5-14(17)27)18(30)24(22,23)36/h3-6,13,16,27,29,34-36H,7-9H2,1-2H3,(H,25,26)(H,32,33)/t13-,16-,21+,22-,23+,24+/m1/s1

> <INCHI_KEY>
JTSMUTXXQIUBJR-UHFFFAOYSA-N

> <FORMULA>
C24H25NO11S

> <MOLECULAR_WEIGHT>
535.52

> <EXACT_MASS>
535.114831803

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.514372018415585

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-{[(4aS,6R,6aS,12aS,12bS)-4a,6,8,12a,12b-pentahydroxy-3-methyl-1,7,12-trioxo-1,4,4a,5,6,6a,7,12,12a,12b-decahydrotetraphen-6a-yl]sulfanyl}-2-acetamidopropanoic acid

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-1.0425663686666653

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.094750698069166

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.093160188606472

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2414777611348873

> <JCHEM_POLAR_SURFACE_AREA>
218.75999999999996

> <JCHEM_REFRACTIVITY>
127.12519999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(4aS,6R,6aS,12aS,12bS)-4a,6,8,12a,12b-pentahydroxy-3-methyl-1,7,12-trioxo-5,6-dihydro-4H-tetraphen-6a-yl]sulfanyl}-2-acetamidopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    5.6030    1.3283    2.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9227    1.3050    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030    2.4085    0.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215    0.0889    0.2222 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    0.0604   -1.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4493   -0.5271   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317    0.5669    0.3096 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    0.0151    0.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0605   -1.2622    1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717   -1.2628    2.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -2.5270    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -3.6389    1.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1191   -3.5489    3.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691   -4.7865    1.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929   -4.8676   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -3.7632   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8894   -2.5852   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -1.3848   -1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.5011   -2.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995   -0.0559   -0.5123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2787    0.8232   -1.4444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377    0.3418   -0.4165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0831   -0.8681   -0.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7252    0.9784   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    0.2464   -2.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768    2.3865   -1.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368    3.1001   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042    4.5916   -0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    2.5665    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847    1.0907    0.7851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0923    0.6631    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    0.7967    2.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.0374    1.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1921    0.8240    2.9133 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5989   -0.6954   -2.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6942   -1.2418   -1.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1100   -0.8258   -3.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493    2.0177    2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8744    1.6340    2.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9215    0.2935    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218   -0.7980    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    1.1197   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -1.5489   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -0.4968   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951   -4.3778    3.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543   -5.6812    1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -5.8006   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237   -3.7523   -1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5004    0.5337   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1828   -1.2265    0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1190    2.8548   -2.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7097    4.9917   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    5.1065    0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3684    4.6879   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656    3.0947    1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7103    2.9833    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7703    1.3010    0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0940   -0.2452    2.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    1.4840    2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608    2.0161    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249    1.6081    3.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2213   -1.6766   -3.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  1
 30 32  1  0
 32 33  1  0
 33 34  1  0
  5 35  1  0
 35 36  2  0
 35 37  1  0
 20  8  1  0
 30 22  1  0
 33  8  1  0
 17 11  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  6
  6 43  1  0
  6 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 21 49  1  0
 23 50  1  0
 26 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
 33 60  1  6
 34 61  1  0
 37 62  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       5.603   1.328   2.138  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.923   1.305   0.829  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.703   2.409   0.254  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.521   0.089   0.222  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.854   0.060  -1.062  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.449  -0.527  -0.845  0.00  0.00           C+0
HETATM    7  S   UNK     0       1.632   0.567   0.310  0.00  0.00           S+0
HETATM    8  C   UNK     0      -0.078   0.015   0.706  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.061  -1.262   1.441  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.672  -1.263   2.537  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.471  -2.527   0.969  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.550  -3.639   1.811  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.119  -3.549   3.128  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.069  -4.787   1.255  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.493  -4.868  -0.047  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.407  -3.763  -0.861  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.889  -2.585  -0.338  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.769  -1.385  -1.140  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.555  -1.501  -2.367  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.900  -0.056  -0.512  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.279   0.823  -1.444  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.338   0.342  -0.417  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.083  -0.868  -0.436  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.725   0.978  -1.690  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.827   0.246  -2.708  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.977   2.386  -1.766  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.037   3.100  -0.687  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.304   4.592  -0.781  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.862   2.567   0.649  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.785   1.091   0.785  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.092   0.663   1.155  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.964   0.797   2.025  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.542   1.037   1.726  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.192   0.824   2.913  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.599  -0.695  -2.071  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.694  -1.242  -1.796  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.110  -0.826  -3.359  0.00  0.00           O+0
HETATM   38  H   UNK     0       6.449   2.018   2.090  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.874   1.634   2.925  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.922   0.294   2.373  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.722  -0.798   0.731  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.755   1.120  -1.396  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.595  -1.549  -0.503  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.939  -0.497  -1.827  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.195  -4.378   3.700  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.154  -5.681   1.862  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.905  -5.801  -0.467  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.724  -3.752  -1.913  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.500   0.534  -2.355  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.183  -1.226   0.460  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.119   2.855  -2.762  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.710   4.992  -1.642  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.111   5.106   0.157  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.368   4.688  -1.075  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.966   3.095   1.097  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.710   2.983   1.278  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.770   1.301   0.867  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.094  -0.245   2.361  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.330   1.484   2.834  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.261   2.016   1.355  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.725   1.608   3.159  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.221  -1.677  -3.894  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   41                                                  
CONECT    5    4    6   35   42                                             
CONECT    6    5    7   43   44                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   20   33                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   45                                                       
CONECT   14   12   15   46                                                  
CONECT   15   14   16   47                                                  
CONECT   16   15   17   48                                                  
CONECT   17   16   18   11                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22    8                                             
CONECT   21   20   49                                                       
CONECT   22   20   23   24   30                                             
CONECT   23   22   50                                                       
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   51                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   52   53   54                                             
CONECT   29   27   30   55   56                                             
CONECT   30   29   31   32   22                                             
CONECT   31   30   57                                                       
CONECT   32   30   33   58   59                                             
CONECT   33   32   34    8   60                                             
CONECT   34   33   61                                                       
CONECT   35    5   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   62                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   21                                                            
CONECT   50   23                                                            
CONECT   51   26                                                            
CONECT   52   28                                                            
CONECT   53   28                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
CONECT   56   29                                                            
CONECT   57   31                                                            
CONECT   58   32                                                            
CONECT   59   32                                                            
CONECT   60   33                                                            
CONECT   61   34                                                            
CONECT   62   37                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    5.6030    1.3283    2.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9227    1.3050    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030    2.4085    0.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215    0.0889    0.2222 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8541    0.0604   -1.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4493   -0.5271   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317    0.5669    0.3096 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    0.0151    0.7057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0605   -1.2622    1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717   -1.2628    2.5365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -2.5270    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499   -3.6389    1.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1191   -3.5489    3.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691   -4.7865    1.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929   -4.8676   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -3.7632   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8894   -2.5852   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691   -1.3848   -1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.5011   -2.3672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995   -0.0559   -0.5123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2787    0.8232   -1.4444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3377    0.3418   -0.4165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0831   -0.8681   -0.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7252    0.9784   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    0.2464   -2.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9768    2.3865   -1.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368    3.1001   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042    4.5916   -0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621    2.5665    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847    1.0907    0.7851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0923    0.6631    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    0.7967    2.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.0374    1.7265 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1921    0.8240    2.9133 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5989   -0.6954   -2.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6942   -1.2418   -1.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1100   -0.8258   -3.3589 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4493    2.0177    2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8744    1.6340    2.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9215    0.2935    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7218   -0.7980    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    1.1197   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5952   -1.5489   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393   -0.4968   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951   -4.3778    3.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543   -5.6812    1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049   -5.8006   -0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7237   -3.7523   -1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5004    0.5337   -2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1828   -1.2265    0.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1190    2.8548   -2.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7097    4.9917   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111    5.1065    0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3684    4.6879   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656    3.0947    1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7103    2.9833    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7703    1.3010    0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0940   -0.2452    2.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300    1.4840    2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608    2.0161    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249    1.6081    3.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2213   -1.6766   -3.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  1
 30 32  1  0
 32 33  1  0
 33 34  1  0
  5 35  1  0
 35 36  2  0
 35 37  1  0
 20  8  1  0
 30 22  1  0
 33  8  1  0
 17 11  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  6
  6 43  1  0
  6 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 21 49  1  0
 23 50  1  0
 26 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 32 59  1  0
 33 60  1  6
 34 61  1  0
 37 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-[(4a,6,8,12a,12b-Pentahydroxy-3-methyl-1,7,12-trioxo-1,4,4a,5,6,6a,7,12,12a,12b-decahydrotetraphen-6a-yl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoate	Generator
3-[(4a,6,8,12a,12b-Pentahydroxy-3-methyl-1,7,12-trioxo-1,4,4a,5,6,6a,7,12,12a,12b-decahydrotetraphen-6a-yl)sulphanyl]-2-[(1-hydroxyethylidene)amino]propanoate	Generator
3-[(4a,6,8,12a,12b-Pentahydroxy-3-methyl-1,7,12-trioxo-1,4,4a,5,6,6a,7,12,12a,12b-decahydrotetraphen-6a-yl)sulphanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid	Generator
WS 009b	MeSH

Chemical Formula

C₂₄H₂₅NO₁₁S

Average Mass

535.5200 Da

Monoisotopic Mass

535.11483 Da

IUPAC Name

(2S)-3-{[(4aS,6R,6aS,12aS,12bS)-4a,6,8,12a,12b-pentahydroxy-3-methyl-1,7,12-trioxo-1,4,4a,5,6,6a,7,12,12a,12b-decahydrotetraphen-6a-yl]sulfanyl}-2-acetamidopropanoic acid

Traditional Name

(2S)-3-{[(4aS,6R,6aS,12aS,12bS)-4a,6,8,12a,12b-pentahydroxy-3-methyl-1,7,12-trioxo-5,6-dihydro-4H-tetraphen-6a-yl]sulfanyl}-2-acetamidopropanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC(CSC12C(O)CC3(O)CC(C)=CC(=O)C3(O)C1(O)C(=O)C1=C(C(O)=CC=C1)C2=O)C(O)=O

InChI Identifier

InChI=1S/C24H25NO11S/c1-10-6-15(28)23(35)21(34,7-10)8-16(29)22(37-9-13(20(32)33)25-11(2)26)19(31)17-12(4-3-5-14(17)27)18(30)24(22,23)36/h3-6,13,16,27,29,34-36H,7-9H2,1-2H3,(H,25,26)(H,32,33)

InChI Key

JTSMUTXXQIUBJR-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, 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 sp.	NPAtlas	1325433

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid or derivatives
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
Quinone
Cyclohexenone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Cyclic alcohol
Tertiary alcohol
Acetamide
Vinylogous acid
Carboxamide group
Ketone
Secondary alcohol
Secondary carboxylic acid amide
Polyol
Thioether
Sulfenyl compound
Carboxylic acid derivative
Dialkylthioether
Carboxylic acid
Monocarboxylic acid or derivatives
Organosulfur compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Alcohol
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	0.02	ALOGPS
logP	-1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.09	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	218.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.13 m³·mol⁻¹	ChemAxon
Polarizability	50.51 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA016773

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9931638

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11756937

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miyata S, Ohhata N, Murai H, Masui Y, Ezaki M, Takase S, Nishikawa M, Kiyoto S, Okuhara M, Kohsaka M: WS009 A and B, new endothelin receptor antagonists isolated from Streptomyces sp. no. 89009. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1992 Jul;45(7):1029-40. doi: 10.7164/antibiotics.45.1029. [PubMed:1325433 ]
Authors unspecified: Lung Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389497 ]
Authors unspecified: Endometrial Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:26389486 ]
Authors unspecified: Ewing Sarcoma and Undifferentiated Small Round Cell Sarcomas of Bone and Soft Tissue Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389480 ]
Authors unspecified: Bladder Cancer Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389479 ]

Showing NP-Card for WS 009 B (NP0004758)

MOL for NP0004758 (WS 009 B)

3D MOL for NP0004758 (WS 009 B)

3D SDF for NP0004758 (WS 009 B)

3D-SDF for NP0004758 (WS 009 B)

PDB for NP0004758 (WS 009 B)

3D PDB for NP0004758 (WS 009 B)

SMILES for NP0004758 (WS 009 B)

INCHI for NP0004758 (WS 009 B)

Structure for NP0004758 (WS 009 B)

3D Structure for NP0004758 (WS 009 B)