NP-MRD: Showing NP-Card for Azythromycin (NP0334693)

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Record Information

Version

2.0

Created at

2024-09-10 19:33:11 UTC

Updated at

2024-09-10 19:33:12 UTC

NP-MRD ID

NP0334693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Azythromycin

Description

Azythromycin belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Azithromycin is an azalide, a subclass of macrolide antibiotics. Azythromycin is a very strong basic compound (based on its pKa). In humans, azythromycin is involved in azithromycin action pathway. Azithromycin is derived from erythromycin; however, it differs chemically from erythromycin in that a methyl-substituted nitrogen atom is incorporated into the lactone ring, thus making the lactone ring 15-membered. Azithromycin is sold under the brand names Zithromax ("Zmax") and Sumamed, and is one of the world's best-selling antibiotics. Azithromycin is used to treat certain bacterial infections, most often bacteria causing middle ear infections, tonsillitis, throat infections, laryngitis, bronchitis, pneumonia and sinusitis. It is also effective against certain sexually transmitted infectious diseases, such as non-gonococcal urethritis and cervicitis.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231219162D          

 52 54  0  0  1  0            999 V2000
   10.8409  -12.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4455  -10.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1931   -8.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2013   -7.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6146   -9.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7591  -12.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0411   -6.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4604   -8.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8620   -5.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7447  -12.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0680   -5.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6678   -5.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9345  -11.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5675   -4.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8380  -11.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394   -7.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3342   -9.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5139   -6.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0083  -10.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6264  -10.1643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.5751   -7.8768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4183   -8.6786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3388   -9.4907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6154  -11.9928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8654   -6.9099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1214   -6.5219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5747  -11.5733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0725   -7.6746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3392   -6.7838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1675   -9.4533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9237  -11.5247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3069   -6.2130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2282   -8.6626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1143  -10.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1748   -7.5922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5223   -9.4214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1311   -6.2468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2664  -12.0414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2857   -5.7134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2817  -11.4566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7212   -6.2372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0177  -12.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9241   -5.4821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610  -10.6784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8292   -8.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4994  -12.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3440   -5.2934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7928   -8.1388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2482   -7.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7855  -10.7630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6624   -8.8010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3925   -7.8541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
 20  2  1  6  0  0  0
 21  3  1  6  0  0  0
 22  4  1  1  0  0  0
 23  5  1  6  0  0  0
  6 24  1  0  0  0  0
 25  7  1  6  0  0  0
 36  8  1  6  0  0  0
 37  9  1  6  0  0  0
 38 10  1  1  0  0  0
 11 39  1  0  0  0  0
 12 39  1  0  0  0  0
 13 40  1  0  0  0  0
 14 47  1  0  0  0  0
 27 15  1  6  0  0  0
 16 26  1  0  0  0  0
 16 21  1  0  0  0  0
 17 20  1  0  0  0  0
 17 36  1  0  0  0  0
 18 28  1  0  0  0  0
 18 37  1  0  0  0  0
 19 40  1  0  0  0  0
 19 20  1  0  0  0  0
 21 48  1  0  0  0  0
 22 33  1  0  0  0  0
 22 30  1  0  0  0  0
 23 30  1  0  0  0  0
 23 34  1  0  0  0  0
 24 31  1  0  0  0  0
 24 40  1  1  0  0  0
 25 32  1  0  0  0  0
 25 49  1  0  0  0  0
 26 29  1  0  0  0  0
 26 39  1  6  0  0  0
 27 38  1  0  0  0  0
 27 50  1  0  0  0  0
 28 51  1  1  0  0  0
 28 49  1  0  0  0  0
 29 35  1  0  0  0  0
 29 41  1  1  0  0  0
 30 51  1  6  0  0  0
 31 38  1  0  0  0  0
 31 42  1  6  0  0  0
 32 37  1  0  0  0  0
 32 43  1  1  0  0  0
 33 36  1  0  0  0  0
 33 52  1  6  0  0  0
 34 44  2  0  0  0  0
 34 50  1  0  0  0  0
 35 52  1  6  0  0  0
 35 48  1  0  0  0  0
 36 45  1  0  0  0  0
 37 47  1  0  0  0  0
 38 46  1  0  0  0  0
M  END


  Mrv0541 02231219162D          

 52 54  0  0  1  0            999 V2000
   10.8409  -12.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4455  -10.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1931   -8.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2013   -7.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6146   -9.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7591  -12.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0411   -6.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4604   -8.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8620   -5.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7447  -12.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0680   -5.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6678   -5.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9345  -11.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5675   -4.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8380  -11.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7394   -7.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3342   -9.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5139   -6.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0083  -10.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6264  -10.1643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.5751   -7.8768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4183   -8.6786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3388   -9.4907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6154  -11.9928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8654   -6.9099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1214   -6.5219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5747  -11.5733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0725   -7.6746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3392   -6.7838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1675   -9.4533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9237  -11.5247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3069   -6.2130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2282   -8.6626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1143  -10.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1748   -7.5922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5223   -9.4214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1311   -6.2468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2664  -12.0414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2857   -5.7134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2817  -11.4566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7212   -6.2372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0177  -12.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9241   -5.4821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610  -10.6784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8292   -8.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4994  -12.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3440   -5.2934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7928   -8.1388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2482   -7.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7855  -10.7630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6624   -8.8010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3925   -7.8541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
 20  2  1  6  0  0  0
 21  3  1  6  0  0  0
 22  4  1  1  0  0  0
 23  5  1  6  0  0  0
  6 24  1  0  0  0  0
 25  7  1  6  0  0  0
 36  8  1  6  0  0  0
 37  9  1  6  0  0  0
 38 10  1  1  0  0  0
 11 39  1  0  0  0  0
 12 39  1  0  0  0  0
 13 40  1  0  0  0  0
 14 47  1  0  0  0  0
 27 15  1  6  0  0  0
 16 26  1  0  0  0  0
 16 21  1  0  0  0  0
 17 20  1  0  0  0  0
 17 36  1  0  0  0  0
 18 28  1  0  0  0  0
 18 37  1  0  0  0  0
 19 40  1  0  0  0  0
 19 20  1  0  0  0  0
 21 48  1  0  0  0  0
 22 33  1  0  0  0  0
 22 30  1  0  0  0  0
 23 30  1  0  0  0  0
 23 34  1  0  0  0  0
 24 31  1  0  0  0  0
 24 40  1  1  0  0  0
 25 32  1  0  0  0  0
 25 49  1  0  0  0  0
 26 29  1  0  0  0  0
 26 39  1  6  0  0  0
 27 38  1  0  0  0  0
 27 50  1  0  0  0  0
 28 51  1  1  0  0  0
 28 49  1  0  0  0  0
 29 35  1  0  0  0  0
 29 41  1  1  0  0  0
 30 51  1  6  0  0  0
 31 38  1  0  0  0  0
 31 42  1  6  0  0  0
 32 37  1  0  0  0  0
 32 43  1  1  0  0  0
 33 36  1  0  0  0  0
 33 52  1  6  0  0  0
 34 44  2  0  0  0  0
 34 50  1  0  0  0  0
 35 52  1  6  0  0  0
 35 48  1  0  0  0  0
 36 45  1  0  0  0  0
 37 47  1  0  0  0  0
 38 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2C[C@](C)(OC)[C@H](O)[C@@H](C)O2)[C@@H](C)[C@H](O[C@H]2O[C@@H](C)C[C@H]([C@@H]2O)N(C)C)[C@@](C)(O)C[C@H](C)CN(C)[C@@H](C)[C@@H](O)[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23+,24-,25+,26+,27-,28+,29-,30-,31+,32+,33-,35+,36-,37-,38+/m0/s1

> <INCHI_KEY>
MQTOSJVFKKJCRP-HHZDEWPHSA-N

> <FORMULA>
C38H72N2O12

> <MOLECULAR_WEIGHT>
748.9845

> <EXACT_MASS>
748.508525778

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
82.63374062539839

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5S,8S,10S,11S,12R,13S,14R)-11-{[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.4447815993333313

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.89815406880848

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.428323628576404

> <JCHEM_PKA_STRONGEST_BASIC>
9.569664875084948

> <JCHEM_POLAR_SURFACE_AREA>
180.07999999999996

> <JCHEM_REFRACTIVITY>
194.10820000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zithromax IV

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.236 -23.271   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.832 -18.790   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.227 -15.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.776 -14.714   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.814 -17.598   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.684 -24.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.877 -12.835   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.993 -16.733   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.142 -10.946   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.923 -24.021   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.994 -10.176   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.380  -9.645   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.878 -22.327   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.726  -8.964   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.231 -22.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.380 -13.194   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.757 -17.551   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.493 -13.025   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.149 -19.947   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.303 -18.973   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.074 -14.703   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.181 -16.200   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.166 -17.716   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.415 -22.387   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.415 -12.898   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.227 -12.174   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.606 -21.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.669 -14.326   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.767 -12.663   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.713 -17.646   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.124 -21.513   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.240 -11.598   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.693 -16.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      20.747 -19.219   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      26.460 -14.172   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      25.242 -17.587   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      20.778 -11.661   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.897 -22.477   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      28.533 -10.665   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0      26.659 -21.386   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0      25.613 -11.643   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      24.300 -23.017   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      18.525 -10.233   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      19.341 -19.933   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      25.815 -15.948   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      23.332 -24.096   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      21.175  -9.881   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      27.613 -15.192   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      19.130 -14.263   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      22.000 -20.091   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      21.770 -16.429   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      24.999 -14.661   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7   25                                                            
CONECT    8   36                                                            
CONECT    9   37                                                            
CONECT   10   38                                                            
CONECT   11   39                                                            
CONECT   12   39                                                            
CONECT   13   40                                                            
CONECT   14   47                                                            
CONECT   15    1   27                                                       
CONECT   16   26   21                                                       
CONECT   17   20   36                                                       
CONECT   18   28   37                                                       
CONECT   19   40   20                                                       
CONECT   20    2   17   19                                                  
CONECT   21    3   16   48                                                  
CONECT   22    4   33   30                                                  
CONECT   23    5   30   34                                                  
CONECT   24    6   31   40                                                  
CONECT   25    7   32   49                                                  
CONECT   26   16   29   39                                                  
CONECT   27   15   38   50                                                  
CONECT   28   18   51   49                                                  
CONECT   29   26   35   41                                                  
CONECT   30   22   23   51                                                  
CONECT   31   24   38   42                                                  
CONECT   32   25   37   43                                                  
CONECT   33   22   36   52                                                  
CONECT   34   23   44   50                                                  
CONECT   35   29   52   48                                                  
CONECT   36    8   17   33   45                                             
CONECT   37    9   18   32   47                                             
CONECT   38   10   27   31   46                                             
CONECT   39   11   12   26                                                  
CONECT   40   13   19   24                                                  
CONECT   41   29                                                            
CONECT   42   31                                                            
CONECT   43   32                                                            
CONECT   44   34                                                            
CONECT   45   36                                                            
CONECT   46   38                                                            
CONECT   47   14   37                                                       
CONECT   48   21   35                                                       
CONECT   49   25   28                                                       
CONECT   50   27   34                                                       
CONECT   51   28   30                                                       
CONECT   52   33   35                                                       
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

View in JSmol

Synonyms

Value	Source
Azithramycine	HMDB
Azithromycin	HMDB
Azithromycin (aids initiative)	HMDB
Azithromycin dihydrate	HMDB
Azithromycin plus tumor necrosis factor	HMDB
Azithromycin sterile	HMDB
Azithromycine	HMDB
N,N-Dimethyl-4-amino-benzaldehyde	HMDB
ZIT	HMDB
Zithromax	HMDB
Azithromycin monohydrate	MeSH
Goxal	MeSH
Azithromycin pfizer brand	MeSH
Dihydrate, azithromycin	MeSH
Pfizer brand OF azithromycin dihydrate	MeSH
Sumamed	MeSH
Toraseptol	MeSH
Zentavion	MeSH
Monohydrate, azithromycin	MeSH
Azadose	MeSH
Bayer brand OF azithromycin dihydrate	MeSH
Funk brand OF azithromycin dihydrate	MeSH
Pharmacia brand OF azithromycin dihydrate	MeSH
Mack brand OF azithromycin dihydrate	MeSH
Pfizer brand OF azithromycin	MeSH
Azitrocin	MeSH
Ultreon	MeSH
Lesvi brand OF azithromycin dihydrate	MeSH
Vinzam	MeSH
Vita brand OF azithromycin dihydrate	MeSH
Zitromax	MeSH

Chemical Formula

C₃₈H₇₂N₂O₁₂

Average Mass

748.9845 Da

Monoisotopic Mass

748.50853 Da

IUPAC Name

(2S,3S,4R,5S,8S,10S,11S,12R,13S,14R)-11-{[(2R,3S,4R,6S)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2S,4S,5R,6R)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

Traditional Name

zithromax IV

CAS Registry Number

Not Available

SMILES

CC[C@@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2C[C@](C)(OC)[C@H](O)[C@@H](C)O2)[C@@H](C)[C@H](O[C@H]2O[C@@H](C)C[C@H]([C@@H]2O)N(C)C)[C@@](C)(O)C[C@H](C)CN(C)[C@@H](C)[C@@H](O)[C@]1(C)O

InChI Identifier

InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23+,24-,25+,26+,27-,28+,29-,30-,31+,32+,33-,35+,36-,37-,38+/m0/s1

InChI Key

MQTOSJVFKKJCRP-HHZDEWPHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Azacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organopnictogen compound
Amine
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.03	ALOGPS
logP	2.44	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.43	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	194.11 m³·mol⁻¹	ChemAxon
Polarizability	82.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001916

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022735

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

53477736

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Azythromycin (NP0334693)

MOL for NP0334693 (Azythromycin)

3D MOL for NP0334693 (Azythromycin)

3D SDF for NP0334693 (Azythromycin)

3D-SDF for NP0334693 (Azythromycin)

PDB for NP0334693 (Azythromycin)

3D PDB for NP0334693 (Azythromycin)

SMILES for NP0334693 (Azythromycin)

INCHI for NP0334693 (Azythromycin)

Structure for NP0334693 (Azythromycin)

3D Structure for NP0334693 (Azythromycin)