NP-MRD: Showing NP-Card for Bicyclomycin (NP0021428)

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Record Information

Version

2.0

Created at

2021-01-06 06:40:37 UTC

Updated at

2021-07-15 17:36:20 UTC

NP-MRD ID

NP0021428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bicyclomycin

Provided By

NPAtlas

Description

Bicozamycin is also known as bicyclomycin or aizumycin. Bicyclomycin is found in Streptomyces and Streptomyces sapporonensis. Bicyclomycin was first documented in 1972 (PMID: 4648311). Based on a literature review very few articles have been published on Bicozamycin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105153D          

 39 40  0  0  0  0            999 V2000
    4.3624    0.3000   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    0.1729   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.3471   -0.8764 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2924    1.9120    0.0367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0036    1.4820   -0.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485    0.1534    0.1891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4966   -0.2396    0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9004    0.6308    1.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228   -0.2660   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568    1.1186   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.0639   -1.3851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332   -0.7872    0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6311   -2.1100    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    0.0211    1.3844 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -0.8337    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -1.3186    2.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -1.1378    0.1597 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5180   -2.0733    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -1.5693   -0.7450 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -0.6665   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.5717   -2.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8421    1.2135   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714   -0.4942    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    1.1422   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    2.1370   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8014    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    3.0323   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.2320    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    1.5380    1.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    1.6999    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2648    1.6594   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8768    0.9488   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -0.6879   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635   -0.6187   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8403   -0.1876    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.6721    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    0.6266    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137   -1.9381    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948   -2.4689   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  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
  9 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 17  2  1  0  0  0  0
 20  6  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  7 28  1  1  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  0  0  0  0
M  END

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    4.3624    0.3000   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    0.1729   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.3471   -0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2924    1.9120    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036    1.4820   -0.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485    0.1534    0.1891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4966   -0.2396    0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9004    0.6308    1.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228   -0.2660   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568    1.1186   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.0639   -1.3851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332   -0.7872    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -2.1100    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    0.0211    1.3844 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -0.8337    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -1.3186    2.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -1.1378    0.1597 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5180   -2.0733    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -1.5693   -0.7450 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -0.6665   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.5717   -2.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8421    1.2135   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714   -0.4942    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    1.1422   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    2.1370   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8014    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    3.0323   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.2320    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    1.5380    1.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    1.6999    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2648    1.6594   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8768    0.9488   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -0.6879   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635   -0.6187   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8403   -0.1876    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.6721    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    0.6266    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137   -1.9381    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948   -2.4689   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  6  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  1
  8 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv1652306242105153D          

 39 40  0  0  0  0            999 V2000
    4.3624    0.3000   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    0.1729   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.3471   -0.8764 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2924    1.9120    0.0367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0036    1.4820   -0.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485    0.1534    0.1891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4966   -0.2396    0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9004    0.6308    1.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228   -0.2660   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568    1.1186   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.0639   -1.3851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332   -0.7872    0.5142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6311   -2.1100    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    0.0211    1.3844 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -0.8337    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -1.3186    2.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -1.1378    0.1597 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5180   -2.0733    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -1.5693   -0.7450 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -0.6665   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.5717   -2.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8421    1.2135   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714   -0.4942    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    1.1422   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    2.1370   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8014    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    3.0323   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.2320    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    1.5380    1.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    1.6999    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2648    1.6594   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8768    0.9488   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -0.6879   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635   -0.6187   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8403   -0.1876    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.6721    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    0.6266    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137   -1.9381    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948   -2.4689   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  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
  9 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 17  2  1  0  0  0  0
 20  6  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  7 28  1  1  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(O[H])[C@]12OC([H])([H])C([H])([H])C(=C([H])[H])[C@](O[H])(N([H])C1=O)C(=O)N2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O7/c1-6-3-4-21-12(7(16)10(2,19)5-15)9(18)13-11(6,20)8(17)14-12/h7,15-16,19-20H,1,3-5H2,2H3,(H,13,18)(H,14,17)/t7-,10-,11+,12-/m0/s1

> <INCHI_KEY>
WOUDXEYYJPOSNE-VKZDFBPFSA-N

> <FORMULA>
C12H18N2O7

> <MOLECULAR_WEIGHT>
302.2805

> <EXACT_MASS>
302.11140094

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.58893644561805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6R)-6-hydroxy-5-methylidene-1-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione

> <ALOGPS_LOGP>
-1.61

> <JCHEM_LOGP>
-2.3876340640000002

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.983974469922424

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.47241544436124

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1067071257329344

> <JCHEM_POLAR_SURFACE_AREA>
148.35

> <JCHEM_REFRACTIVITY>
67.50219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bicozamycin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    4.3624    0.3000   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    0.1729   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.3471   -0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2924    1.9120    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036    1.4820   -0.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485    0.1534    0.1891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4966   -0.2396    0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9004    0.6308    1.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228   -0.2660   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568    1.1186   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.0639   -1.3851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332   -0.7872    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -2.1100    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    0.0211    1.3844 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -0.8337    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -1.3186    2.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -1.1378    0.1597 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5180   -2.0733    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -1.5693   -0.7450 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -0.6665   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.5717   -2.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8421    1.2135   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714   -0.4942    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    1.1422   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    2.1370   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8014    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    3.0323   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.2320    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    1.5380    1.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    1.6999    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2648    1.6594   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8768    0.9488   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -0.6879   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635   -0.6187   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8403   -0.1876    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.6721    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    0.6266    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137   -1.9381    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948   -2.4689   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  6  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  1
  8 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  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       4.362   0.300  -0.203  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.062   0.173  -0.309  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.325   1.347  -0.876  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.292   1.912   0.037  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.004   1.482  -0.187  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.149   0.153   0.189  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.497  -0.240   0.665  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.900   0.631   1.729  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.623  -0.266  -0.289  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.057   1.119  -0.745  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.530  -1.064  -1.385  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.833  -0.787   0.514  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.631  -2.110   0.882  0.00  0.00           O+0
HETATM   14  N   UNK     0       0.724   0.021   1.384  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.826  -0.834   1.453  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.204  -1.319   2.547  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.527  -1.138   0.160  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.518  -2.073   0.321  0.00  0.00           O+0
HETATM   19  N   UNK     0       1.479  -1.569  -0.745  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.372  -0.667  -0.910  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.178  -0.572  -2.050  0.00  0.00           O+0
HETATM   22  H   UNK     0       4.842   1.214  -0.516  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.971  -0.494   0.195  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.957   1.142  -1.912  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.120   2.137  -1.028  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.646   1.801   1.077  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.267   3.032  -0.130  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.412  -1.232   1.154  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.608   1.538   1.548  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.510   1.700   0.083  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.265   1.659  -1.280  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.877   0.949  -1.483  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.995  -0.688  -2.180  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.763  -0.619  -0.025  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.840  -0.188   1.448  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.672  -2.672   0.073  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.441   0.627   2.193  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.914  -1.938   1.224  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.495  -2.469  -1.259  0.00  0.00           H+0
CONECT    1    2   22   23                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4   24   25                                             
CONECT    4    3    5   26   27                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   14   20                                             
CONECT    7    6    8    9   28                                             
CONECT    8    7   29                                                       
CONECT    9    7   10   11   12                                             
CONECT   10    9   30   31   32                                             
CONECT   11    9   33                                                       
CONECT   12    9   13   34   35                                             
CONECT   13   12   36                                                       
CONECT   14    6   15   37                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19    2                                             
CONECT   18   17   38                                                       
CONECT   19   17   20   39                                                  
CONECT   20   19   21    6                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
    4.3624    0.3000   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    0.1729   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.3471   -0.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2924    1.9120    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0036    1.4820   -0.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485    0.1534    0.1891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4966   -0.2396    0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9004    0.6308    1.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6228   -0.2660   -0.2889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568    1.1186   -0.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -1.0639   -1.3851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8332   -0.7872    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -2.1100    0.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    0.0211    1.3844 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -0.8337    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -1.3186    2.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -1.1378    0.1597 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5180   -2.0733    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794   -1.5693   -0.7450 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719   -0.6665   -0.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -0.5717   -2.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8421    1.2135   -0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714   -0.4942    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    1.1422   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    2.1370   -1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455    1.8014    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    3.0323   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.2320    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    1.5380    1.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    1.6999    0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2648    1.6594   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8768    0.9488   -1.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -0.6879   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635   -0.6187   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8403   -0.1876    1.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.6721    0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4413    0.6266    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137   -1.9381    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948   -2.4689   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  6  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  1
  8 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Aizumycin	ChEBI
Bicozamicina	ChEBI
Bicozamycine	ChEBI
Bicozamycinum	ChEBI
Bicyclomycin	ChEBI
CGP 3543E	MeSH
CGP 354E	MeSH

Chemical Formula

C₁₂H₁₈N₂O₇

Average Mass

302.2805 Da

Monoisotopic Mass

302.11140 Da

IUPAC Name

(1S,6R)-6-hydroxy-5-methylidene-1-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione

Traditional Name

bicozamycin

CAS Registry Number

Not Available

SMILES

C[C@](O)(CO)[C@H](O)[C@@]12NC(=O)[C@@](O)(NC1=O)C(=C)CCO2

InChI Identifier

InChI=1S/C12H18N2O7/c1-6-3-4-21-12(7(16)10(2,19)5-15)9(18)13-11(6,20)8(17)14-12/h7,15-16,19-20H,1,3-5H2,2H3,(H,13,18)(H,14,17)/t7-,10-,11+,12-/m0/s1

InChI Key

WOUDXEYYJPOSNE-VKZDFBPFSA-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	NPAtlas	4648311
Streptomyces cinnamoneus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces sapporonensis WS 4545	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tertiary alcohols. These are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic carboximidic acid
Secondary alcohol
Alkanolamine
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organonitrogen compound
Hydrocarbon derivative
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

azabicycloalkane (CHEBI:60584 )
bridged compound (CHEBI:60584 )

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	-1.6	ALOGPS
logP	-2.4	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	148.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.5 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009159

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018850

Chemspider ID

59222

KEGG Compound ID

C11259

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65807

PDB ID

BCM

ChEBI ID

60584

Good Scents ID

Not Available

References

General References

Miyoshi T, Miyairi N, Aoki H, Kosaka M, Sakai H: Bicyclomycin, a new antibiotic. I. Taxonomy, isolation and characterization. J Antibiot (Tokyo). 1972 Oct;25(10):569-75. doi: 10.7164/antibiotics.25.569. [PubMed:4648311 ]

Showing NP-Card for Bicyclomycin (NP0021428)

MOL for NP0021428 (Bicyclomycin)

3D MOL for NP0021428 (Bicyclomycin)

3D SDF for NP0021428 (Bicyclomycin)

3D-SDF for NP0021428 (Bicyclomycin)

PDB for NP0021428 (Bicyclomycin)

3D PDB for NP0021428 (Bicyclomycin)

SMILES for NP0021428 (Bicyclomycin)

INCHI for NP0021428 (Bicyclomycin)

Structure for NP0021428 (Bicyclomycin)

3D Structure for NP0021428 (Bicyclomycin)