NPASS drugs

Drug Information

Drug ID:	NPD8368
Drug Name:	BMS-275183
Molecular Formula:	C43H59NO16
Canonical SMILES:	COC(=O)O[C@@]12CO[C@@H]1C[C@@H]([C@@]1([C@@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@@H]([C@H](C(C)(C)C)N=C(OC(C)(C)C)O)O)C(=C(C2(C)C)[C@H](C1=O)OC(=O)C)C)C)O
Standard InCHI:	"InChI=1S/C43H59NO16/c1-21-24(57-35(50)28(47)31(38(3,4)5)44-36(51)59-39(6,7)8)19-43(53)33(58-34(49)23-16-14-13-15-17-23)30-41(11,32(48)29(56-22(2)45)27(21)40(43,9)10)25(46)18-26-42(30,20-55-26)60-37(52)54-12/h13-17,24-26,28-31,33,46-47,53H,18-20H2,1-12H3,(H,44,51)/t24-,25-,26+,28+,29+,30-,31+,33-,41+,42-,43+/m0/s1"
Standard InCHIKey:	AHXICHPPXIGCBN-GPWPDEGDSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD8368

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	55960
0.1-0.2	150626
0.2-0.3	4811
0.3-0.4	203
0.4-0.5	53
0.5-0.6	43
0.6-0.7	42
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
Intermediate Similarity	0.7212	NPC471623
Remote Similarity	0.6733	NPC34333
Remote Similarity	0.6733	NPC579874
Remote Similarity	0.6733	NPC603140
Remote Similarity	0.6667	NPC324251
Remote Similarity	0.6667	NPC206211
Remote Similarity	0.6604	NPC537050
Remote Similarity	0.6574	NPC208553
Remote Similarity	0.6574	NPC181964
Remote Similarity	0.6574	NPC317140
Remote Similarity	0.6574	NPC184289
Remote Similarity	0.6574	NPC307628
Remote Similarity	0.6514	NPC33372
Remote Similarity	0.6514	NPC52912
Remote Similarity	0.6514	NPC67246
Remote Similarity	0.6505	NPC204918
Remote Similarity	0.6455	NPC487360
Remote Similarity	0.6455	NPC479182
Remote Similarity	0.6455	NPC479180
Remote Similarity	0.6455	NPC215025
Remote Similarity	0.6455	NPC471629
Remote Similarity	0.6455	NPC306001
Remote Similarity	0.6422	NPC326042
Remote Similarity	0.6389	NPC36607
Remote Similarity	0.6389	NPC594728
Remote Similarity	0.6364	NPC317994
Remote Similarity	0.6364	NPC328571
Remote Similarity	0.6364	NPC514212
Remote Similarity	0.6364	NPC588327
Remote Similarity	0.6339	NPC275170
Remote Similarity	0.6283	NPC486061
Remote Similarity	0.6283	NPC486060
Remote Similarity	0.6273	NPC327158
Remote Similarity	0.6273	NPC533612
Remote Similarity	0.6273	NPC558987
Remote Similarity	0.6273	NPC601797
Remote Similarity	0.6273	NPC603171
Remote Similarity	0.6239	NPC295149
Remote Similarity	0.6228	NPC487361
Remote Similarity	0.6228	NPC22933
Remote Similarity	0.6	NPC155329
Remote Similarity	0.6	NPC114357
Remote Similarity	0.6	NPC25820
Remote Similarity	0.5982	NPC519154
Remote Similarity	0.5913	NPC471606
Remote Similarity	0.5893	NPC102167
Remote Similarity	0.5893	NPC488127
Remote Similarity	0.5877	NPC514511
Remote Similarity	0.5842	NPC582276
Remote Similarity	0.5619	NPC275802
Remote Similarity	0.5619	NPC211426
Remote Similarity	0.5478	NPC599799
Remote Similarity	0.5437	NPC94567
Remote Similarity	0.5437	NPC593428
Remote Similarity	0.5437	NPC605573
Remote Similarity	0.5431	NPC49524
Remote Similarity	0.5431	NPC453583
Remote Similarity	0.5431	NPC453588
Remote Similarity	0.5431	NPC179899
Remote Similarity	0.5431	NPC166498
Remote Similarity	0.5345	NPC200927
Remote Similarity	0.5345	NPC14752
Remote Similarity	0.5345	NPC321072
Remote Similarity	0.5345	NPC215892
Remote Similarity	0.5345	NPC242662
Remote Similarity	0.5339	NPC478329
Remote Similarity	0.5304	NPC327675
Remote Similarity	0.5299	NPC191193
Remote Similarity	0.5283	NPC259144
Remote Similarity	0.5283	NPC127672
Remote Similarity	0.5283	NPC257170
Remote Similarity	0.5259	NPC473300
Remote Similarity	0.5259	NPC327024
Remote Similarity	0.5254	NPC471754
Remote Similarity	0.5254	NPC479183
Remote Similarity	0.5254	NPC298358
Remote Similarity	0.5254	NPC479181
Remote Similarity	0.5214	NPC327699
Remote Similarity	0.521	NPC3125
Remote Similarity	0.5169	NPC317882
Remote Similarity	0.514	NPC219419
Remote Similarity	0.5126	NPC327764
Remote Similarity	0.5085	NPC473490
Remote Similarity	0.5085	NPC324957
Remote Similarity	0.5042	NPC328084
Remote Similarity	0.5042	NPC512088

Drug Structure

NPD8368 OpenBabel08211713012D 64 68 0 0 1 0 0 0 0 0999 V2000 -3.0729 -0.5505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3156 -1.5215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8638 3.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4228 2.2901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6642 2.5216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1689 3.7850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6997 4.3935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6658 2.5854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4623 -3.1071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5521 -3.2269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2389 -0.8482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0637 -3.3098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1658 -3.0330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8144 -2.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6069 -3.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9042 -2.0650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6966 -3.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7951 1.3772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0871 -1.3893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9181 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4359 -1.2118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4054 -1.6413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3452 -2.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7187 -0.9758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5903 0.9181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6985 -1.9196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9039 0.7010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9362 -1.0328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7951 -0.4591 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6323 1.2599 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4771 -0.2376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5575 -1.3459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4350 -2.6735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0557 1.0524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2090 1.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0608 -2.1853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5125 2.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8175 2.9367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9034 -2.3787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5903 0.0000 0.0000 C 0 0 1 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 -1.0166 -2.1410 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4806 0.9086 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0540 -2.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3854 1.3772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0238 -0.2093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0360 0.4908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8760 -3.4019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9358 1.9626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0572 1.1162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9477 -1.9477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6900 -2.9991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8232 -3.0721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9181 0.9181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8464 -0.9129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5989 -0.0655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0836 -1.8253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0891 2.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2376 -0.8868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3854 2.2953 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8720 -0.5606 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7856 1.6751 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2698 -3.7110 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 38 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 6 39 1 0 0 0 0 7 39 1 0 0 0 0 8 39 1 0 0 0 0 9 40 1 0 0 0 0 10 40 1 0 0 0 0 12 54 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 43 1 0 0 0 0 20 42 1 0 0 0 0 20 55 1 0 0 0 0 21 24 1 0 0 0 0 21 27 2 0 0 0 0 22 45 2 0 0 0 0 22 56 1 0 0 0 0 23 34 1 0 0 0 0 24 57 1 1 0 0 0 25 41 1 1 0 0 0 25 46 1 0 0 0 0 26 42 1 1 0 0 0 26 55 1 0 0 0 0 27 29 1 0 0 0 0 27 40 1 0 0 0 0 28 31 1 0 0 0 0 28 35 1 6 0 0 0 28 47 1 0 0 0 0 29 32 1 0 0 0 0 29 56 1 1 0 0 0 30 33 1 0 0 0 0 30 41 1 1 0 0 0 30 42 1 0 0 0 0 31 38 1 0 0 0 0 31 44 1 1 0 0 0 32 41 1 0 0 0 0 32 48 2 0 0 0 0 33 43 1 6 0 0 0 33 58 1 0 0 0 0 34 49 2 0 0 0 0 34 58 1 0 0 0 0 35 50 2 0 0 0 0 35 57 1 0 0 0 0 36 44 2 3 0 0 0 36 51 1 0 0 0 0 36 59 1 0 0 0 0 37 52 2 0 0 0 0 37 54 1 0 0 0 0 37 60 1 0 0 0 0 39 59 1 0 0 0 0 40 43 1 0 0 0 0 41 11 1 1 0 0 0 42 60 1 6 0 0 0 43 53 1 6 0 0 0 46 61 1 0 0 0 0 47 62 1 0 0 0 0 51 63 1 0 0 0 0 53 64 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB011554
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

Drug Properties

Molecular Weight	845.38
ALogP	2.1606
MLogP	4.32
XLogP	4.097
HDA	17
HBD	4
Rotatable Bonds	32
TPSA	243.24
RO5 Violation	2