NP-MRD: Showing NP-Card for Antibiotic OA 6129B1 (NP0062154)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 06:49:10 UTC

Updated at

2022-04-28 06:49:10 UTC

NP-MRD ID

NP0062154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Antibiotic OA 6129B1

Description

(5S,6S)-3-({2-[(1-hydroxy-3-{[(2R)-1,2,4-trihydroxy-3,3-dimethylbutylidene]amino}propylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. Antibiotic OA 6129B1 is found in Streptomyces sp. OA-6129. Based on a literature review very few articles have been published on (5S,6S)-3-({2-[(1-hydroxy-3-{[(2R)-1,2,4-trihydroxy-3,3-dimethylbutylidene]amino}propylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208492D          

 32 33  0  0  1  0            999 V2000
   -1.6026    1.3461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1901    0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4036   -0.1653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    1.0441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8881    1.7586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3361    2.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314    1.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444    0.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -0.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7291    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321    2.4486    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755    2.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899    3.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4189    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334    2.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8478    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8478    3.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5623    2.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2768    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9912    2.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7057    2.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8643    3.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6893    1.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5623    1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3995    1.5596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9828    0.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    2.3565    0.0000 O   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
  5  4  1  6  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 24 28  1  0  0  0  0
 23 29  1  1  0  0  0
  1 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  1  1  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    8.7976    1.2404    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2768    1.1135    0.1499 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9140    1.9580   -0.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9830   -0.3239   -0.1186 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0441   -1.2094    1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9420   -1.7689    1.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319   -1.1484    1.1202 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2717   -1.2098    1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360   -2.1137    2.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821   -2.2001    2.9925 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688   -2.9310    3.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5165   -0.3746    0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187    0.0222    0.8085 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588   -0.1032    2.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153    0.2723    1.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1408   -0.6266    0.7625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5573   -1.5080   -0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037   -1.7064   -1.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7794   -2.3897    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -2.4029   -1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3441   -1.1838   -1.4421 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9628    0.1154   -1.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069    0.4160   -1.7184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8207    1.3081   -1.9114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0715    2.4752   -1.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0437    1.4573   -1.1030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6352    2.8472   -1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1231    0.4642   -1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8712    1.4329    0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3025    0.2439    0.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4851    0.2994   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5356   -0.7235   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2930    0.4732   -0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1006    1.1004    1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1799    2.2168   -0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8331    1.4365    1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7076    2.3562   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5987   -0.7405   -0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6363   -3.9525    3.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5591   -1.1396    2.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139    0.5564    3.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7813    1.3336    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943    0.1205    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -0.1880   -0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3586   -2.0262    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3902   -3.3942    0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0864   -2.7198   -2.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4051   -3.2411   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4300   -1.3214   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1688    1.1894   -2.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5813    2.5281   -2.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0081    3.6062   -1.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6649    2.8358   -1.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7147    2.8965   -2.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8747    0.0294   -2.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3386   -0.2987   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0721    1.0608   -1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8909    1.4594    0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3307    2.3278    0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9902   -0.4135    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    1.1564    0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488    0.5599   -1.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3602   -1.5498   -1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4 32  1  0
 32 31  1  0
 31 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  1
 26 28  1  0
 26 29  1  0
 29 30  1  0
 12  8  2  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  5  4  1  0
  7 32  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  4 38  1  6
 32 63  1  6
 31 61  1  0
 31 62  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 24 50  1  6
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 11 39  1  0
M  END


  Mrv1652304282208492D          

 32 33  0  0  1  0            999 V2000
   -1.6026    1.3461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1901    0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4036   -0.1653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    1.0441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8881    1.7586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3361    2.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314    1.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444    0.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -0.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7291    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321    2.4486    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755    2.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899    3.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4189    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334    2.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8478    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8478    3.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5623    2.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2768    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9912    2.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7057    2.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8643    3.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6893    1.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5623    1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3995    1.5596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9828    0.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    2.3565    0.0000 O   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
  5  4  1  6  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 24 28  1  0  0  0  0
 23 29  1  1  0  0  0
  1 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@@H]1[C@@H]2CC(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO)=C(N2C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H31N3O8S/c1-10(25)14-11-8-12(15(19(30)31)23(11)18(14)29)32-7-6-21-13(26)4-5-22-17(28)16(27)20(2,3)9-24/h10-11,14,16,24-25,27H,4-9H2,1-3H3,(H,21,26)(H,22,28)(H,30,31)/t10-,11+,14-,16+/m1/s1

> <INCHI_KEY>
HNLNYXRYILRJHY-KTMIJUKYSA-N

> <FORMULA>
C20H31N3O8S

> <MOLECULAR_WEIGHT>
473.54

> <EXACT_MASS>
473.183186144

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.818865378867635

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6S)-3-[(2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}ethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.49

> <JCHEM_LOGP>
-3.359244368333333

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.682311088719697

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8114502347919714

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0126099842570673

> <JCHEM_POLAR_SURFACE_AREA>
176.49999999999997

> <JCHEM_REFRACTIVITY>
117.02209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S)-3-[(2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}ethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-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      -2.991   2.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.221   1.179   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.620  -0.309   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -0.888   1.949   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.658   3.283   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.627   4.427   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.780   3.801   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.619   2.269   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.763   1.239   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.443  -0.268   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.228   1.715   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0       2.113   4.571   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0       3.447   3.801   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.781   4.571   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       6.114   3.801   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       7.448   4.571   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.448   6.111   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.782   3.801   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.115   4.571   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      11.449   3.801   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      12.783   4.571   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.783   6.111   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.116   3.801   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.450   4.571   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.784   5.341   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      18.117   4.571   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.680   5.904   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.220   3.237   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.116   2.261   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.479   2.911   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.568   1.822   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.878   4.399   0.000  0.00  0.00           O+0
CONECT    1    2    5   30                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   27   28                                             
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24                                                            
CONECT   28   24                                                            
CONECT   29   23                                                            
CONECT   30    1   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
(5S,6S)-3-({2-[(1-hydroxy-3-{[(2R)-1,2,4-trihydroxy-3,3-dimethylbutylidene]amino}propylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
(5S,6S)-3-({2-[(1-hydroxy-3-{[(2R)-1,2,4-trihydroxy-3,3-dimethylbutylidene]amino}propylidene)amino]ethyl}sulphanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
(5S,6S)-3-({2-[(1-hydroxy-3-{[(2R)-1,2,4-trihydroxy-3,3-dimethylbutylidene]amino}propylidene)amino]ethyl}sulphanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator

Chemical Formula

C₂₀H₃₁N₃O₈S

Average Mass

473.5400 Da

Monoisotopic Mass

473.18319 Da

IUPAC Name

(5S,6S)-3-[(2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}ethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Traditional Name

(5S,6S)-3-[(2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}ethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@@H]1[C@@H]2CC(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO)=C(N2C1=O)C(O)=O

InChI Identifier

InChI=1S/C20H31N3O8S/c1-10(25)14-11-8-12(15(19(30)31)23(11)18(14)29)32-7-6-21-13(26)4-5-22-17(28)16(27)20(2,3)9-24/h10-11,14,16,24-25,27H,4-9H2,1-3H3,(H,21,26)(H,22,28)(H,30,31)/t10-,11+,14-,16+/m1/s1

InChI Key

HNLNYXRYILRJHY-KTMIJUKYSA-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. OA-6129	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Thienamycins

Alternative Parents

Substituents

Thienamycin
Alpha-amino acid or derivatives
Pyrroline carboxylic acid or derivatives
Pyrroline carboxylic acid
Azepine
Vinylogous thioester
Tertiary carboxylic acid amide
Pyrroline
Thioenolether
Secondary alcohol
Carboxamide group
Azetidine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.49	ALOGPS
logP	-3.4	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	176.5 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	117.02 m³·mol⁻¹	ChemAxon
Polarizability	48.82 Å³	ChemAxon
Number of Rings	2	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

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

162905570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Antibiotic OA 6129B1 (NP0062154)

MOL for NP0062154 (Antibiotic OA 6129B1)

3D MOL for NP0062154 (Antibiotic OA 6129B1)

3D SDF for NP0062154 (Antibiotic OA 6129B1)

3D-SDF for NP0062154 (Antibiotic OA 6129B1)

PDB for NP0062154 (Antibiotic OA 6129B1)

3D PDB for NP0062154 (Antibiotic OA 6129B1)

SMILES for NP0062154 (Antibiotic OA 6129B1)

INCHI for NP0062154 (Antibiotic OA 6129B1)

Structure for NP0062154 (Antibiotic OA 6129B1)

3D Structure for NP0062154 (Antibiotic OA 6129B1)