NPASS drugs

Drug Information

Drug ID:	NPD5544
Drug Name:	Clomocycline
Molecular Formula:	C23H25ClN2O9
Canonical SMILES:	OCN=C(C1=C(O)[C@@H](N(C)C)[C@H]2[C@](C1=O)(O)C(=C1[C@H](C2)[C@](C)(O)c2c(C1=O)c(O)ccc2Cl)O)O
Standard InCHI:	InChI=1S/C23H25ClN2O9/c1-22(34)8-6-9-16(26(2)3)18(30)14(21(33)25-7-27)20(32)23(9,35)19(31)12(8)17(29)13-11(28)5-4-10(24)15(13)22/h4-5,8-9,16,27-28,30-31,34-35H,6-7H2,1-3H3,(H,25,33)/t8-,9-,16-,22-,23-/m0/s1
Standard InCHIKey:	GJGDLRSSCNAKGL-KMVLDZISSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD5544

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	229
0.1-0.2	1122
0.2-0.3	3628
0.3-0.4	8582
0.4-0.5	7193
0.5-0.6	9334
0.6-0.7	796
0.7-0.8	1
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	0.9722	NPC96730
High Similarity	0.9719	NPC39528
High Similarity	0.8827	NPC291305
High Similarity	0.8791	NPC295531
High Similarity	0.8571	NPC469973
Intermediate Similarity	0.76	NPC317727
Remote Similarity	0.6976	NPC264938
Remote Similarity	0.6952	NPC68967
Remote Similarity	0.6919	NPC476444
Remote Similarity	0.681	NPC313274
Remote Similarity	0.6802	NPC12890
Remote Similarity	0.6762	NPC42286
Remote Similarity	0.6757	NPC297322
Remote Similarity	0.6698	NPC316164
Remote Similarity	0.6682	NPC314941
Remote Similarity	0.6667	NPC315889
Remote Similarity	0.665	NPC329790
Remote Similarity	0.6649	NPC29932
Remote Similarity	0.6635	NPC196231
Remote Similarity	0.663	NPC305060
Remote Similarity	0.662	NPC314596
Remote Similarity	0.6618	NPC209865
Remote Similarity	0.6616	NPC314693
Remote Similarity	0.6596	NPC143898
Remote Similarity	0.6591	NPC315253
Remote Similarity	0.6587	NPC453583
Remote Similarity	0.6587	NPC475336
Remote Similarity	0.6587	NPC473300
Remote Similarity	0.6579	NPC136878
Remote Similarity	0.6579	NPC285122
Remote Similarity	0.6574	NPC314946
Remote Similarity	0.6573	NPC1991
Remote Similarity	0.6566	NPC101207
Remote Similarity	0.6564	NPC314257
Remote Similarity	0.6562	NPC44378
Remote Similarity	0.6562	NPC280753
Remote Similarity	0.6555	NPC67246
Remote Similarity	0.6555	NPC33372
Remote Similarity	0.655	NPC329647
Remote Similarity	0.655	NPC470735
Remote Similarity	0.6538	NPC246693
Remote Similarity	0.6538	NPC242358
Remote Similarity	0.6538	NPC58685
Remote Similarity	0.6538	NPC110609
Remote Similarity	0.6536	NPC471530
Remote Similarity	0.6531	NPC280497
Remote Similarity	0.6526	NPC170055
Remote Similarity	0.6512	NPC286135
Remote Similarity	0.651	NPC94781
Remote Similarity	0.651	NPC112816
Remote Similarity	0.6507	NPC317882
Remote Similarity	0.6507	NPC471754
Remote Similarity	0.6495	NPC205918
Remote Similarity	0.6493	NPC289223
Remote Similarity	0.648	NPC3224
Remote Similarity	0.648	NPC231774
Remote Similarity	0.6478	NPC316461
Remote Similarity	0.6474	NPC79627
Remote Similarity	0.6474	NPC300684
Remote Similarity	0.6474	NPC48130
Remote Similarity	0.6474	NPC84568
Remote Similarity	0.6474	NPC218866
Remote Similarity	0.6473	NPC288854
Remote Similarity	0.6471	NPC474857
Remote Similarity	0.6465	NPC470559
Remote Similarity	0.6464	NPC278928
Remote Similarity	0.6462	NPC191193
Remote Similarity	0.6462	NPC321072
Remote Similarity	0.6462	NPC215892
Remote Similarity	0.6462	NPC242662
Remote Similarity	0.6456	NPC477816
Remote Similarity	0.6456	NPC298339
Remote Similarity	0.6455	NPC469520
Remote Similarity	0.6455	NPC85310
Remote Similarity	0.6448	NPC17843
Remote Similarity	0.6447	NPC470564
Remote Similarity	0.6439	NPC73555
Remote Similarity	0.6436	NPC131078
Remote Similarity	0.6436	NPC301846
Remote Similarity	0.6435	NPC97086
Remote Similarity	0.6432	NPC471606
Remote Similarity	0.6432	NPC208553
Remote Similarity	0.6432	NPC181964
Remote Similarity	0.6429	NPC191606
Remote Similarity	0.6429	NPC306001
Remote Similarity	0.6429	NPC70340
Remote Similarity	0.6429	NPC473400
Remote Similarity	0.6429	NPC275170
Remote Similarity	0.6429	NPC206211
Remote Similarity	0.6429	NPC324251
Remote Similarity	0.6429	NPC471629
Remote Similarity	0.6425	NPC470479
Remote Similarity	0.6421	NPC199936
Remote Similarity	0.6419	NPC261012
Remote Similarity	0.6419	NPC314738
Remote Similarity	0.6419	NPC109403
Remote Similarity	0.6409	NPC767
Remote Similarity	0.6409	NPC247250
Remote Similarity	0.6408	NPC264922
Remote Similarity	0.6402	NPC83019
Remote Similarity	0.6402	NPC473558
Remote Similarity	0.6402	NPC293624
Remote Similarity	0.64	NPC313582
Remote Similarity	0.6398	NPC272268
Remote Similarity	0.6398	NPC315275
Remote Similarity	0.6396	NPC68727
Remote Similarity	0.6389	NPC151470
Remote Similarity	0.6389	NPC64576
Remote Similarity	0.6389	NPC476662
Remote Similarity	0.6389	NPC201055
Remote Similarity	0.6389	NPC254045
Remote Similarity	0.6389	NPC306765
Remote Similarity	0.6387	NPC477409
Remote Similarity	0.6386	NPC163924
Remote Similarity	0.6386	NPC54661
Remote Similarity	0.6385	NPC473371
Remote Similarity	0.6382	NPC15506
Remote Similarity	0.6374	NPC146647
Remote Similarity	0.6374	NPC34414
Remote Similarity	0.6373	NPC256935
Remote Similarity	0.6373	NPC315406
Remote Similarity	0.6373	NPC108948
Remote Similarity	0.6373	NPC184518
Remote Similarity	0.6369	NPC74507
Remote Similarity	0.6369	NPC234890
Remote Similarity	0.6369	NPC310540
Remote Similarity	0.6368	NPC94499
Remote Similarity	0.6364	NPC472623
Remote Similarity	0.6364	NPC245923
Remote Similarity	0.6364	NPC147418
Remote Similarity	0.6364	NPC151292
Remote Similarity	0.6359	NPC67346
Remote Similarity	0.6359	NPC70622
Remote Similarity	0.6359	NPC243483
Remote Similarity	0.6359	NPC315520
Remote Similarity	0.6359	NPC232533
Remote Similarity	0.6355	NPC204580
Remote Similarity	0.6354	NPC471683
Remote Similarity	0.6351	NPC470103
Remote Similarity	0.6347	NPC475768
Remote Similarity	0.6347	NPC80472
Remote Similarity	0.6346	NPC132751
Remote Similarity	0.6345	NPC470408
Remote Similarity	0.6345	NPC474824
Remote Similarity	0.6345	NPC182921
Remote Similarity	0.6345	NPC312482
Remote Similarity	0.6345	NPC218870
Remote Similarity	0.6344	NPC473055
Remote Similarity	0.6344	NPC283088
Remote Similarity	0.6344	NPC473052
Remote Similarity	0.6343	NPC472392
Remote Similarity	0.6343	NPC476661
Remote Similarity	0.6343	NPC313541
Remote Similarity	0.6341	NPC277865
Remote Similarity	0.6341	NPC470580
Remote Similarity	0.6339	NPC55949
Remote Similarity	0.6337	NPC470081
Remote Similarity	0.6335	NPC471682
Remote Similarity	0.6333	NPC162694
Remote Similarity	0.6332	NPC252156
Remote Similarity	0.633	NPC230811
Remote Similarity	0.633	NPC173980
Remote Similarity	0.6327	NPC284236
Remote Similarity	0.6327	NPC316368
Remote Similarity	0.6326	NPC315351
Remote Similarity	0.6326	NPC473490
Remote Similarity	0.6326	NPC316412
Remote Similarity	0.6324	NPC115458
Remote Similarity	0.6324	NPC129578
Remote Similarity	0.6324	NPC171968
Remote Similarity	0.6324	NPC477115
Remote Similarity	0.6324	NPC4170
Remote Similarity	0.6319	NPC237225
Remote Similarity	0.6318	NPC472405
Remote Similarity	0.6316	NPC477275
Remote Similarity	0.6314	NPC213529
Remote Similarity	0.6313	NPC472391
Remote Similarity	0.6313	NPC3449
Remote Similarity	0.6311	NPC313708
Remote Similarity	0.631	NPC322526
Remote Similarity	0.631	NPC471201
Remote Similarity	0.631	NPC474813
Remote Similarity	0.631	NPC474311
Remote Similarity	0.6308	NPC477566
Remote Similarity	0.6308	NPC478219
Remote Similarity	0.6308	NPC477567
Remote Similarity	0.6308	NPC120171
Remote Similarity	0.6305	NPC73544
Remote Similarity	0.6304	NPC244699
Remote Similarity	0.6304	NPC205992
Remote Similarity	0.6304	NPC17083
Remote Similarity	0.6303	NPC471623
Remote Similarity	0.6302	NPC103910
Remote Similarity	0.6298	NPC328287
Remote Similarity	0.6296	NPC103337
Remote Similarity	0.6296	NPC114620
Remote Similarity	0.6294	NPC470337
Remote Similarity	0.6294	NPC478220
Remote Similarity	0.6294	NPC268992
Remote Similarity	0.6294	NPC470340

Drug Structure

NPD5544 OpenBabel08211708292D 42 45 0 0 1 0 0 0 0 0999 V2000 3.2333 -2.1591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2360 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2360 -2.4457 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 1.4674 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -2.4457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6378 -1.8418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 3.4239 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 1.9565 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -2.4457 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 1.9565 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 0.4891 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5101 -2.8116 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 2.4457 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 25 1 0 0 0 0 7 27 1 0 0 0 0 8 12 1 0 0 0 0 8 22 1 1 0 0 0 9 16 1 0 0 0 0 9 23 1 1 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 13 2 0 0 0 0 11 28 1 0 0 0 0 12 17 1 0 0 0 0 12 19 2 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 29 2 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 23 1 0 0 0 0 20 32 2 0 0 0 0 21 25 2 3 0 0 0 21 33 1 0 0 0 0 22 1 1 6 0 0 0 22 34 1 0 0 0 0 23 35 1 6 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 30 38 1 0 0 0 0 31 39 1 0 0 0 0 33 40 1 0 0 0 0 34 41 1 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000882
DrugBank	DB00453
ChEMBL	CHEMBL2106071
IUPHAR/BPS
PharmaGKB	PA164771235
KEGG Drug	D06885
PubChem CID
ChEBI	59589
CAS Number	1181-54-0

Drug Properties

Molecular Weight	508.12
ALogP	-3.6335
MLogP	2.67
XLogP	0.161
HDA	10
HBD	7
Rotatable Bonds	14
TPSA	191.35
RO5 Violation	1