NPASS drugs

Drug Information

Drug ID:	NPD5035
Drug Name:	doxycycline
Molecular Formula:	C22H24N2O8
Canonical SMILES:	CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1[C@@H](O)[C@@H]1[C@@H](C)c3cccc(c3C(=C1C2=O)O)O)O)O)C(=N)O)C
Standard InCHI:	InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
Standard InCHIKey:	SGKRLCUYIXIAHR-AKNGSSGZSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5035

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	176
0.1-0.2	879
0.2-0.3	2124
0.3-0.4	6091
0.4-0.5	7563
0.5-0.6	8741
0.6-0.7	5262
0.7-0.8	50
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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	0.8895	NPC469973
High Similarity	0.88	NPC295531
High Similarity	0.8514	NPC291305
Intermediate Similarity	0.8	NPC96730
Intermediate Similarity	0.7789	NPC39528
Intermediate Similarity	0.7656	NPC317727
Intermediate Similarity	0.7363	NPC314693
Intermediate Similarity	0.7318	NPC314257
Intermediate Similarity	0.7308	NPC101207
Intermediate Similarity	0.7283	NPC54661
Intermediate Similarity	0.7283	NPC163924
Intermediate Similarity	0.7268	NPC289223
Intermediate Similarity	0.7259	NPC313274
Intermediate Similarity	0.7257	NPC136878
Intermediate Similarity	0.7208	NPC42286
Intermediate Similarity	0.72	NPC314941
Intermediate Similarity	0.7198	NPC313582
Intermediate Similarity	0.7188	NPC329790
Intermediate Similarity	0.7167	NPC472211
Intermediate Similarity	0.7151	NPC205918
Intermediate Similarity	0.7143	NPC79627
Intermediate Similarity	0.7143	NPC29932
Intermediate Similarity	0.7143	NPC17843
Intermediate Similarity	0.7135	NPC44378
Intermediate Similarity	0.7135	NPC280753
Intermediate Similarity	0.7118	NPC473052
Intermediate Similarity	0.7118	NPC473055
Intermediate Similarity	0.7097	NPC329647
Intermediate Similarity	0.7097	NPC470735
Intermediate Similarity	0.7094	NPC315889
Intermediate Similarity	0.7088	NPC474861
Intermediate Similarity	0.7085	NPC261012
Intermediate Similarity	0.7085	NPC314738
Intermediate Similarity	0.7085	NPC109403
Intermediate Similarity	0.7079	NPC94781
Intermediate Similarity	0.7079	NPC112816
Intermediate Similarity	0.7079	NPC68967
Intermediate Similarity	0.7076	NPC322526
Intermediate Similarity	0.7062	NPC285122
Intermediate Similarity	0.7062	NPC209865
Intermediate Similarity	0.705	NPC316164
Intermediate Similarity	0.7033	NPC68727
Intermediate Similarity	0.702	NPC281629
Intermediate Similarity	0.7017	NPC51824
Intermediate Similarity	0.7017	NPC113608
Intermediate Similarity	0.7017	NPC470337
Intermediate Similarity	0.7017	NPC180944
Intermediate Similarity	0.7017	NPC470340
Intermediate Similarity	0.7017	NPC268992
Intermediate Similarity	0.7017	NPC470338
Intermediate Similarity	0.7011	NPC15506
Intermediate Similarity	0.7006	NPC170055
Intermediate Similarity	0.7005	NPC12890
Intermediate Similarity	0.7	NPC294501
Remote Similarity	0.6985	NPC316412
Remote Similarity	0.6985	NPC315351
Remote Similarity	0.6984	NPC315406
Remote Similarity	0.6982	NPC328070
Remote Similarity	0.6979	NPC477816
Remote Similarity	0.6978	NPC155686
Remote Similarity	0.6978	NPC218870
Remote Similarity	0.6978	NPC182921
Remote Similarity	0.6978	NPC474824
Remote Similarity	0.6978	NPC470408
Remote Similarity	0.6977	NPC315275
Remote Similarity	0.6961	NPC314596
Remote Similarity	0.6949	NPC471906
Remote Similarity	0.6949	NPC2672
Remote Similarity	0.6949	NPC84568
Remote Similarity	0.6949	NPC469856
Remote Similarity	0.6949	NPC48130
Remote Similarity	0.6949	NPC218866
Remote Similarity	0.6949	NPC469854
Remote Similarity	0.6949	NPC300684
Remote Similarity	0.6949	NPC244691
Remote Similarity	0.6948	NPC252156
Remote Similarity	0.6947	NPC470580
Remote Similarity	0.6947	NPC478021
Remote Similarity	0.694	NPC156348
Remote Similarity	0.694	NPC69043
Remote Similarity	0.694	NPC478230
Remote Similarity	0.6939	NPC473300
Remote Similarity	0.6939	NPC475336
Remote Similarity	0.6939	NPC453583
Remote Similarity	0.6936	NPC305060
Remote Similarity	0.6935	NPC316457
Remote Similarity	0.6932	NPC85310
Remote Similarity	0.6932	NPC291078
Remote Similarity	0.6932	NPC474961
Remote Similarity	0.6932	NPC469520
Remote Similarity	0.6931	NPC477115
Remote Similarity	0.6923	NPC478220
Remote Similarity	0.6915	NPC471031
Remote Similarity	0.6915	NPC469689
Remote Similarity	0.6912	NPC314946
Remote Similarity	0.6911	NPC473113
Remote Similarity	0.6911	NPC313708
Remote Similarity	0.6906	NPC225854
Remote Similarity	0.6905	NPC247250
Remote Similarity	0.6905	NPC767
Remote Similarity	0.6904	NPC67246
Remote Similarity	0.6904	NPC33372
Remote Similarity	0.6893	NPC143898
Remote Similarity	0.6891	NPC298339
Remote Similarity	0.6885	NPC312482
Remote Similarity	0.6885	NPC478231
Remote Similarity	0.6885	NPC137301
Remote Similarity	0.6882	NPC472055
Remote Similarity	0.6882	NPC284495
Remote Similarity	0.6879	NPC471201
Remote Similarity	0.6875	NPC91019
Remote Similarity	0.6875	NPC106519
Remote Similarity	0.6872	NPC471970
Remote Similarity	0.6868	NPC132990
Remote Similarity	0.6868	NPC46882
Remote Similarity	0.6865	NPC29552
Remote Similarity	0.6865	NPC472889
Remote Similarity	0.6862	NPC328494
Remote Similarity	0.686	NPC175870
Remote Similarity	0.6853	NPC471754
Remote Similarity	0.6853	NPC70340
Remote Similarity	0.6853	NPC317882
Remote Similarity	0.6851	NPC120171
Remote Similarity	0.6851	NPC477221
Remote Similarity	0.6848	NPC208173
Remote Similarity	0.6848	NPC471456
Remote Similarity	0.6848	NPC474501
Remote Similarity	0.6848	NPC472890
Remote Similarity	0.6848	NPC170189
Remote Similarity	0.6842	NPC110609
Remote Similarity	0.6842	NPC478190
Remote Similarity	0.6842	NPC246693
Remote Similarity	0.6842	NPC242358
Remote Similarity	0.6842	NPC473094
Remote Similarity	0.6839	NPC19056
Remote Similarity	0.6839	NPC475957
Remote Similarity	0.6839	NPC470583
Remote Similarity	0.6836	NPC30846
Remote Similarity	0.6836	NPC471971
Remote Similarity	0.6836	NPC471972
Remote Similarity	0.6836	NPC193555
Remote Similarity	0.6836	NPC469855
Remote Similarity	0.6836	NPC135524
Remote Similarity	0.6836	NPC137649
Remote Similarity	0.6836	NPC248068
Remote Similarity	0.6832	NPC108487
Remote Similarity	0.6831	NPC76041
Remote Similarity	0.6831	NPC115249
Remote Similarity	0.6831	NPC478224
Remote Similarity	0.6831	NPC184284
Remote Similarity	0.6828	NPC314795
Remote Similarity	0.6828	NPC470339
Remote Similarity	0.6826	NPC127975
Remote Similarity	0.6825	NPC472049
Remote Similarity	0.6823	NPC270027
Remote Similarity	0.6818	NPC136649
Remote Similarity	0.6813	NPC48949
Remote Similarity	0.6813	NPC315520
Remote Similarity	0.6811	NPC478027
Remote Similarity	0.6811	NPC313299
Remote Similarity	0.6809	NPC315772
Remote Similarity	0.6809	NPC472059
Remote Similarity	0.6806	NPC473096
Remote Similarity	0.6806	NPC473095
Remote Similarity	0.6802	NPC279045
Remote Similarity	0.6802	NPC471749
Remote Similarity	0.6802	NPC113325
Remote Similarity	0.68	NPC215892
Remote Similarity	0.68	NPC321072
Remote Similarity	0.68	NPC242662
Remote Similarity	0.68	NPC251439
Remote Similarity	0.68	NPC173980
Remote Similarity	0.68	NPC191193
Remote Similarity	0.6798	NPC64576
Remote Similarity	0.6798	NPC254045
Remote Similarity	0.6798	NPC201055
Remote Similarity	0.6798	NPC151470
Remote Similarity	0.6793	NPC476194
Remote Similarity	0.6793	NPC478218
Remote Similarity	0.6791	NPC323965
Remote Similarity	0.6789	NPC178173
Remote Similarity	0.6788	NPC469393
Remote Similarity	0.6788	NPC154986
Remote Similarity	0.6786	NPC71610
Remote Similarity	0.6782	NPC86524
Remote Similarity	0.678	NPC305845
Remote Similarity	0.678	NPC204045
Remote Similarity	0.6778	NPC314437
Remote Similarity	0.6778	NPC470330
Remote Similarity	0.6778	NPC143685
Remote Similarity	0.6774	NPC478225
Remote Similarity	0.6774	NPC474637
Remote Similarity	0.6772	NPC476931
Remote Similarity	0.6772	NPC472053
Remote Similarity	0.6769	NPC115447
Remote Similarity	0.6769	NPC470582
Remote Similarity	0.6769	NPC470581
Remote Similarity	0.6769	NPC266513
Remote Similarity	0.6768	NPC206211
Remote Similarity	0.6768	NPC473400

Drug Structure

NPD5035 OpenBabel08211706322D 39 42 0 0 1 0 0 0 0 0999 V2000 2.5377 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3835 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3835 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5377 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 0.4884 0.0000 C 0 0 0 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 -3.3835 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -2.4419 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2294 0.4884 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -2.9302 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4419 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 7 1 1 6 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 1 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 12 16 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 1 0 0 0 15 18 1 0 0 0 0 15 24 1 6 0 0 0 16 26 1 0 0 0 0 17 27 1 6 0 0 0 18 28 2 0 0 0 0 19 22 1 0 0 0 0 19 29 2 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 23 2 0 0 0 0 21 31 1 0 0 0 0 22 32 1 6 0 0 0 23 33 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 30 37 1 0 0 0 0 31 38 1 0 0 0 0 32 39 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP100399
DrugBank
ChEMBL
IUPHAR/BPS	6464
PharmaGKB
KEGG Drug
PubChem CID	54671203
ChEBI
CAS Number

Drug Properties

Molecular Weight	444.15
ALogP	-3.0535
MLogP	2.78
XLogP	1.137
HDA	9
HBD	7
Rotatable Bonds	11
TPSA	182.61
RO5 Violation	1