NP-MRD: Showing NP-Card for (4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid (NP0179495)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 17:41:31 UTC

Updated at

2022-09-03 17:41:31 UTC

NP-MRD ID

NP0179495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid

Description

(4S,4aS,6S,12aR)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-1,4,4a,5,6,11,12,12a-octahydrotetracene-2-carboximidic acid, also known as dehydrochlortetracycline, belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups. (4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid is found in Apis cerana. Based on a literature review very few articles have been published on (4S,4aS,6S,12aR)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-1,4,4a,5,6,11,12,12a-octahydrotetracene-2-carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219412D          

 33 36  0  0  1  0            999 V2000
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
  4 20  1  0  0  0  0
 13 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -6.0276    1.6826    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5016    2.5314    1.2315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176    2.7470    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9451    4.1211    0.8696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    1.7370    0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5034    0.4355    0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602   -0.0325    0.9550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4882   -0.5977    0.3407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9067   -1.6103   -0.5397 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1717   -2.8102   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -1.3661   -1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1363   -0.0886   -0.0401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1643   -0.0997    1.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2197    0.0349    0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    1.0516   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063    1.3673   -0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    2.3475   -1.5892 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8140    0.5394   -0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916    0.8740   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2299    1.9548   -1.7269 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1859    0.1466   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0075   -0.9106    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291   -1.2363    0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5340   -2.5742    1.9170 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6205   -0.5184    0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -0.9190    0.9159 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9951   -2.2920    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -1.0413    2.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118    1.8378   -0.6379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716    3.0241   -0.9998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    1.3156   -0.6016 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7147    1.3686   -1.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536    2.2215    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117    3.3006    0.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1168    4.6458    0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9226   -0.8613    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3364   -1.1119    1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7205   -3.5643   -1.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9745   -3.1623    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855   -2.6183   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6411   -0.6284   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404   -2.3504   -1.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3635   -1.0236   -2.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555   -0.6900   -0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -1.1253    1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3764    0.6755    1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1280    2.2206   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1749    0.4163   -0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8514   -1.5128    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3388   -2.1352   -0.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5344   -2.9147    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364   -2.7531   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -1.9076    2.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060    1.8591   -2.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9 11  1  0
  9  8  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  1
 15 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  6
 31 33  1  0
 33 34  2  0
 33  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
 31 12  1  0
 26 14  1  0
 25 18  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
  8 37  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 27 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 32 54  1  0
  4 35  1  0
  2  1  1  0
  7 36  1  0
M  END


  Mrv1652309032219412D          

 33 36  0  0  1  0            999 V2000
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
  4 20  1  0  0  0  0
 13 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0179495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)[C@H]1[C@@H]2CC3=C(C(=O)C4=C(O)C=CC(Cl)=C4[C@@]3(C)O)C(=O)[C@]2(O)C(=O)C(C(O)=N)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H21ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,8,15,26,28,32-33H,6H2,1-3H3,(H2,24,31)/t8-,15-,21-,22-/m0/s1

> <INCHI_KEY>
ZWVGXYMEBVFNGR-GUQUGOGCSA-N

> <FORMULA>
C22H21ClN2O8

> <MOLECULAR_WEIGHT>
476.87

> <EXACT_MASS>
476.0986433

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.34819114147504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,4aS,6S,12aR)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-1,4,4a,5,6,11,12,12a-octahydrotetracene-2-carboximidic acid

> <JCHEM_LOGP>
-4.178229022184996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
1.3317313047742028

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.9164118150905196

> <JCHEM_PKA_STRONGEST_BASIC>
13.907722853442968

> <JCHEM_POLAR_SURFACE_AREA>
179.45

> <JCHEM_REFRACTIVITY>
128.4388

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aS,6S,12aR)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4H-tetracene-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.336  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      13.337   1.540   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.991  -1.950   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.011  -1.950   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   27  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   32                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19    4   13                                                  
CONECT   21   18   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   31                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31   17   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Dehydrochlortetracycline	Kegg
5a,11a-Dehydro-7-chlorotetracycline	Kegg
(4S,4AS,6S,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-1,4,4a,5,6,11,12,12a-octahydrotetracene-2-carboximidate	Generator

Chemical Formula

C₂₂H₂₁ClN₂O₈

Average Mass

476.8700 Da

Monoisotopic Mass

476.09864 Da

IUPAC Name

(4S,4aS,6S,12aR)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-1,4,4a,5,6,11,12,12a-octahydrotetracene-2-carboximidic acid

Traditional Name

(4S,4aS,6S,12aR)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4H-tetracene-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

CN(C)[C@H]1[C@@H]2CC3=C(C(=O)C4=C(O)C=CC(Cl)=C4[C@@]3(C)O)C(=O)[C@]2(O)C(=O)C(C(O)=N)=C1O

InChI Identifier

InChI=1S/C22H21ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,8,15,26,28,32-33H,6H2,1-3H3,(H2,24,31)/t8-,15-,21-,22-/m0/s1

InChI Key

ZWVGXYMEBVFNGR-GUQUGOGCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tetracyclines

Sub Class

Not Available

Direct Parent

Tetracyclines

Alternative Parents

Substituents

Tetracycline
Naphthalene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aryl chloride
Aryl halide
Benzenoid
Tertiary alcohol
Vinylogous acid
Ketone
Tertiary aliphatic amine
Tertiary amine
Carboximidic acid
Carboximidic acid derivative
Enol
Polyol
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Amine
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tetracyclines (CHEBI:81649 )

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	-4.2	ChemAxon
pKa (Strongest Acidic)	-2.9	ChemAxon
pKa (Strongest Basic)	13.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	128.44 m³·mol⁻¹	ChemAxon
Polarizability	45.35 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30791385

KEGG Compound ID

C18298

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid (NP0179495)

MOL for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

3D MOL for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

3D SDF for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

3D-SDF for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

PDB for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

3D PDB for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

SMILES for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

INCHI for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

Structure for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)

3D Structure for NP0179495 ((4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-3,6,10,12a-tetrahydroxy-6-methyl-1,11,12-trioxo-4a,5-dihydro-4h-tetracene-2-carboximidic acid)