NP-MRD: Showing NP-Card for (-)-Maremycin E (NP0068922)

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Record Information

Version

2.0

Created at

2022-04-28 14:11:41 UTC

Updated at

2022-04-28 14:11:41 UTC

NP-MRD ID

NP0068922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Maremycin E

Description

(5S,6S,6aS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulfanyl)methyl]-2',3-dioxo-1',2',3,4,5,6a,7,8-octahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-9-carboxylic acid belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (-)-Maremycin E is found in Streptomyces sp.(GT051237). Based on a literature review very few articles have been published on (5S,6S,6aS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulfanyl)methyl]-2',3-dioxo-1',2',3,4,5,6a,7,8-octahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-9-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216112D          

 32 36  0  0  1  0            999 V2000
    3.6087    0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1449   -0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9559   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308    0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    1.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835    1.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -1.0691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9119   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -1.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467   -0.0546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8677    0.7702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1640    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561    2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785    2.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199    2.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0088    2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    3.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -0.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219   -0.4487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8470   -1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934   -0.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103    0.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -0.3758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0108    0.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    1.2372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929    1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    0.8796    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    0.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857    0.6630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305   -1.8311    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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  6  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  6  0  0  0
 20 23  1  0  0  0  0
 23 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
 19 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 31  1  6  0  0  0
  7 32  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    4.6467    0.8628   -2.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5186    0.3281   -1.1771 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830    1.1785    0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5748    0.8346    0.6512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497   -0.0198   -0.1043 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -0.2702    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0113    0.3006    1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7259    1.1430    2.1523 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944    1.4104    1.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    2.1976    2.4546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3706   -0.1266    1.6653 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9457    0.7441    2.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618   -0.0162    0.3846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9751    1.3749   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262    1.9532   -0.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2439    1.9874   -0.1567 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5739    3.3509   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2070    1.0319    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    1.1222    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3445    0.0491    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846   -1.1277    1.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231   -1.2627    1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985   -0.1515    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -0.9094   -0.6906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8940   -0.3191   -1.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -2.2972   -0.7520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074   -2.8055   -1.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587   -2.2795   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432   -2.9067   -1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558   -2.4421   -0.8075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086   -4.0540   -2.1151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958   -1.1927   -0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    1.8943   -2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    0.7612   -3.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8223    0.1198   -2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6575    0.8513    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1195    2.2772    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544    1.6044    3.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3914   -1.1753    2.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    1.8056    2.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957    0.5470    2.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722    0.5201    3.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307    4.0533    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242    3.4072   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083    3.7052   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0927    2.0543    0.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4353    0.0899    0.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2475   -1.9988    1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -2.2060    1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0756    0.1489   -2.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -2.9205    0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2178   -2.4017   -1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -3.8899   -1.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4712   -2.2513   -2.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913   -4.6845   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 23  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 13 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 28 32  2  0
  9  4  1  0
 23 13  1  0
 32 24  1  0
 32  6  1  0
 19 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  8 38  1  0
 11 39  1  1
 12 40  1  0
 12 41  1  0
 12 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 22 49  1  0
 21 48  1  0
 20 47  1  0
 19 46  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 31 55  1  0
M  END


  Mrv1652304282216112D          

 32 36  0  0  1  0            999 V2000
    3.6087    0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1449   -0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9559   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308    0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    1.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8835    1.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -1.0691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9119   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -1.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8467   -0.0546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8677    0.7702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1640    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561    2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785    2.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199    2.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0088    2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    3.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -0.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219   -0.4487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8470   -1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934   -0.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103    0.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -0.3758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0108    0.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    1.2372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929    1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    0.8796    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    0.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857    0.6630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305   -1.8311    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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  6  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  6  0  0  0
 20 23  1  0  0  0  0
 23 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
 19 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 31  1  6  0  0  0
  7 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCC1=NC2=C(NC1=O)[C@@H](C)[C@@]1(C(=O)N(C)C3=C1C=CC=C3)[C@]1(O)CCC(C(O)=O)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C23H23N3O5S/c1-11-17-18(24-14(10-32-3)19(27)25-17)16-12(20(28)29)8-9-22(16,31)23(11)13-6-4-5-7-15(13)26(2)21(23)30/h4-7,11,31H,8-10H2,1-3H3,(H,25,27)(H,28,29)/t11-,22+,23-/m1/s1

> <INCHI_KEY>
HFXOVDHQTGZBCE-SZGOTMDKSA-N

> <FORMULA>
C23H23N3O5S

> <MOLECULAR_WEIGHT>
453.51

> <EXACT_MASS>
453.135842027

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
46.96154991099761

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6S,6aS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulfanyl)methyl]-2',3-dioxo-1',2',3,4,5,6a,7,8-octahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-9-carboxylic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
0.6120854036666679

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.122620569427985

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.163047899627488

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1018677668609995

> <JCHEM_POLAR_SURFACE_AREA>
119.30000000000001

> <JCHEM_REFRACTIVITY>
121.04319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S,6aS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulfanyl)methyl]-2',3-dioxo-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-9-carboxylic acid

> <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       6.736   0.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.737  -0.682   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.251  -0.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.764   1.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.763   2.222   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.249   1.940   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.933  -1.996   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.436  -1.637   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.265  -2.638   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.314  -0.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.353   1.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.039   2.241   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.398   3.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.933   3.861   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.523   2.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.397   4.909   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.883   4.628   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.910   6.361   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.687   1.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.647  -0.034   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.961  -0.838   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.448  -2.290   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.294  -0.769   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -0.019   0.034   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.372  -0.701   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.020   1.574   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       1.373   2.309   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -1.293   2.378   0.000  0.00  0.00           C+0
HETATM   29  S   UNK     0      -2.646   1.642   0.000  0.00  0.00           S+0
HETATM   30  C   UNK     0      -2.686   0.102   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.880   1.238   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.524  -3.418   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8   32                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    1   11   21                                             
CONECT   11   10   12   15   31                                             
CONECT   12   11   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12   20   27                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   10   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26   19                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   11                                                            
CONECT   32    7                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(5S,6S,6AS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulfanyl)methyl]-2',3-dioxo-1',2',3,4,5,6a,7,8-octahydrospiro[cyclopenta[F]quinoxaline-6,3'-indole]-9-carboxylate	Generator
(5S,6S,6AS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulphanyl)methyl]-2',3-dioxo-1',2',3,4,5,6a,7,8-octahydrospiro[cyclopenta[F]quinoxaline-6,3'-indole]-9-carboxylate	Generator
(5S,6S,6AS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulphanyl)methyl]-2',3-dioxo-1',2',3,4,5,6a,7,8-octahydrospiro[cyclopenta[F]quinoxaline-6,3'-indole]-9-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₃N₃O₅S

Average Mass

453.5100 Da

Monoisotopic Mass

453.13584 Da

IUPAC Name

(5S,6S,6aS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulfanyl)methyl]-2',3-dioxo-1',2',3,4,5,6a,7,8-octahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-9-carboxylic acid

Traditional Name

(5S,6S,6aS)-6a-hydroxy-1',5-dimethyl-2-[(methylsulfanyl)methyl]-2',3-dioxo-4,5,7,8-tetrahydrospiro[cyclopenta[f]quinoxaline-6,3'-indole]-9-carboxylic acid

CAS Registry Number

Not Available

SMILES

CSCC1=NC2=C(NC1=O)[C@@H](C)[C@@]1(C(=O)N(C)C3=C1C=CC=C3)[C@]1(O)CCC(C(O)=O)=C21

InChI Identifier

InChI=1S/C23H23N3O5S/c1-11-17-18(24-14(10-32-3)19(27)25-17)16-12(20(28)29)8-9-22(16,31)23(11)13-6-4-5-7-15(13)26(2)21(23)30/h4-7,11,31H,8-10H2,1-3H3,(H,25,27)(H,28,29)/t11-,22+,23-/m1/s1

InChI Key

HFXOVDHQTGZBCE-SZGOTMDKSA-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.(GT051237)	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Benzenoid
Pyrazine
Heteroaromatic compound
Tertiary carboxylic acid amide
Tertiary alcohol
Lactam
Carboxamide group
Azacycle
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.86	ALOGPS
logP	0.61	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	121.04 m³·mol⁻¹	ChemAxon
Polarizability	46.96 Å³	ChemAxon
Number of Rings	5	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

163048360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Maremycin E (NP0068922)

MOL for NP0068922 ((-)-Maremycin E)

3D MOL for NP0068922 ((-)-Maremycin E)

3D SDF for NP0068922 ((-)-Maremycin E)

3D-SDF for NP0068922 ((-)-Maremycin E)

PDB for NP0068922 ((-)-Maremycin E)

3D PDB for NP0068922 ((-)-Maremycin E)

SMILES for NP0068922 ((-)-Maremycin E)

INCHI for NP0068922 ((-)-Maremycin E)

Structure for NP0068922 ((-)-Maremycin E)

3D Structure for NP0068922 ((-)-Maremycin E)