NPASS drugs

Drug Information

Drug ID:	NPD8361
Drug Name:	Docetaxel
Molecular Formula:	C43H53NO14
Canonical SMILES:	CC(=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](c3ccccc3)N=C(OC(C)(C)C)O)O)C(=C(C2(C)C)[C@H](C1=O)O)C)C)O
Standard InCHI:	"InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1"
Standard InCHIKey:	ZDZOTLJHXYCWBA-VCVYQWHSSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD8361

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	42507
0.1-0.2	161997
0.2-0.3	6798
0.3-0.4	248
0.4-0.5	70
0.5-0.6	60
0.6-0.7	28
0.7-0.8	14
0.8-0.85	8
0.85-0.9	5
0.9-0.95	0
0.95-1	2

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
High Similarity	1.0	NPC102167
High Similarity	1.0	NPC488127
High Similarity	0.8526	NPC200927
High Similarity	0.8526	NPC14752
High Similarity	0.8526	NPC321072
High Similarity	0.8526	NPC215892
High Similarity	0.8526	NPC242662
Intermediate Similarity	0.8438	NPC49524
Intermediate Similarity	0.8438	NPC453583
Intermediate Similarity	0.8438	NPC179899
Intermediate Similarity	0.8351	NPC471754
Intermediate Similarity	0.8351	NPC479183
Intermediate Similarity	0.8351	NPC298358
Intermediate Similarity	0.8351	NPC479181
Intermediate Similarity	0.8247	NPC471623
Intermediate Similarity	0.7426	NPC599799
Intermediate Similarity	0.7228	NPC327675
Intermediate Similarity	0.7184	NPC317882
Intermediate Similarity	0.7157	NPC473300
Intermediate Similarity	0.7157	NPC327024
Intermediate Similarity	0.7115	NPC33372
Intermediate Similarity	0.7115	NPC52912
Intermediate Similarity	0.7115	NPC67246
Intermediate Similarity	0.7048	NPC478329
Intermediate Similarity	0.7019	NPC208553
Intermediate Similarity	0.7019	NPC181964
Intermediate Similarity	0.7019	NPC184289
Intermediate Similarity	0.7019	NPC307628
Intermediate Similarity	0.7019	NPC191193
Remote Similarity	0.6952	NPC324251
Remote Similarity	0.6952	NPC206211
Remote Similarity	0.6923	NPC478328
Remote Similarity	0.6887	NPC487360
Remote Similarity	0.6887	NPC479182
Remote Similarity	0.6887	NPC3125
Remote Similarity	0.6887	NPC479180
Remote Similarity	0.6887	NPC215025
Remote Similarity	0.6887	NPC471629
Remote Similarity	0.6887	NPC306001
Remote Similarity	0.6759	NPC275170
Remote Similarity	0.6697	NPC486061
Remote Similarity	0.6697	NPC486060
Remote Similarity	0.6636	NPC487361
Remote Similarity	0.6636	NPC22933
Remote Similarity	0.6604	NPC327699
Remote Similarity	0.6325	NPC472375
Remote Similarity	0.6316	NPC32519
Remote Similarity	0.6316	NPC289383
Remote Similarity	0.6293	NPC289155
Remote Similarity	0.625	NPC229545
Remote Similarity	0.625	NPC316568
Remote Similarity	0.625	NPC248265
Remote Similarity	0.625	NPC134685
Remote Similarity	0.625	NPC585150
Remote Similarity	0.625	NPC603810
Remote Similarity	0.6154	NPC479186
Remote Similarity	0.602	NPC175014
Remote Similarity	0.5979	NPC305902
Remote Similarity	0.5963	NPC537050
Remote Similarity	0.5946	NPC326042
Remote Similarity	0.5905	NPC34333
Remote Similarity	0.5905	NPC579874
Remote Similarity	0.5905	NPC603140
Remote Similarity	0.5893	NPC317994
Remote Similarity	0.5893	NPC328571
Remote Similarity	0.5893	NPC327764
Remote Similarity	0.5893	NPC514212
Remote Similarity	0.5893	NPC588327
Remote Similarity	0.5804	NPC453588
Remote Similarity	0.5804	NPC317140
Remote Similarity	0.5804	NPC166498
Remote Similarity	0.5766	NPC36607
Remote Similarity	0.5766	NPC594728
Remote Similarity	0.5701	NPC204918
Remote Similarity	0.57	NPC94567
Remote Similarity	0.57	NPC593428
Remote Similarity	0.57	NPC605573
Remote Similarity	0.5664	NPC327158
Remote Similarity	0.5664	NPC328084
Remote Similarity	0.5664	NPC512088
Remote Similarity	0.5664	NPC533612
Remote Similarity	0.5664	NPC558987
Remote Similarity	0.5664	NPC601797
Remote Similarity	0.5664	NPC603171
Remote Similarity	0.5492	NPC472391
Remote Similarity	0.5492	NPC27650
Remote Similarity	0.5492	NPC479173
Remote Similarity	0.5487	NPC295149
Remote Similarity	0.5484	NPC241312
Remote Similarity	0.5484	NPC479184
Remote Similarity	0.547	NPC471606
Remote Similarity	0.5455	NPC116862
Remote Similarity	0.5431	NPC514511
Remote Similarity	0.534	NPC155329
Remote Similarity	0.534	NPC119099
Remote Similarity	0.534	NPC11588
Remote Similarity	0.534	NPC114357
Remote Similarity	0.534	NPC25820
Remote Similarity	0.534	NPC582276
Remote Similarity	0.534	NPC587832
Remote Similarity	0.5328	NPC472392
Remote Similarity	0.5323	NPC479185
Remote Similarity	0.5288	NPC79477
Remote Similarity	0.5288	NPC595336
Remote Similarity	0.5259	NPC473558
Remote Similarity	0.5259	NPC519154
Remote Similarity	0.5146	NPC197037
Remote Similarity	0.5146	NPC91730
Remote Similarity	0.5146	NPC66403
Remote Similarity	0.5146	NPC549021
Remote Similarity	0.514	NPC275802
Remote Similarity	0.514	NPC211426
Remote Similarity	0.5098	NPC250343
Remote Similarity	0.5096	NPC246777
Remote Similarity	0.5096	NPC556569
Remote Similarity	0.5093	NPC5681
Remote Similarity	0.5043	NPC473490

Drug Structure

NPD8361 OpenBabel08211713012D 63 68 0 0 1 0 0 0 0 0999 V2000 -3.0315 -0.5431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9214 -1.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6238 3.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8286 1.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6075 3.7952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4292 -3.0653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5312 -3.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2222 -0.8368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0805 0.2031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0828 -2.9922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9622 1.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3619 -0.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5314 -3.7108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7362 -2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1254 1.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5250 -0.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6334 -3.5926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8382 -2.0372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7844 1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0724 -1.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9058 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4031 -1.1954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0465 -2.1559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4068 0.8964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2868 -2.7558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 -0.9626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5688 0.9058 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9058 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6622 -1.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5700 1.2430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8966 -1.0189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8514 0.6916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7844 -0.4529 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4438 -0.2344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5500 -1.3278 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3887 -2.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0145 1.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1703 2.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7258 2.8972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8778 -2.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5688 -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 -1.0029 -2.1122 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4517 2.1410 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5777 -3.9057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3533 1.3587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7947 -0.9006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9696 -0.2064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9952 0.4842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8373 -3.3561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 1.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0521 3.5904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6807 -2.9588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9058 0.9058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5774 -0.0646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0421 -1.8007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2344 -0.8749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0072 2.3458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3533 2.2644 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3461 -1.6192 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8064 -0.5531 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7707 4.1418 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2527 -3.6610 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 39 1 0 0 0 0 4 39 1 0 0 0 0 5 39 1 0 0 0 0 6 40 1 0 0 0 0 7 40 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 24 2 0 0 0 0 16 24 1 0 0 0 0 17 25 2 0 0 0 0 18 25 1 0 0 0 0 19 27 1 0 0 0 0 19 28 1 0 0 0 0 20 26 1 0 0 0 0 20 43 1 0 0 0 0 21 42 1 0 0 0 0 21 54 1 0 0 0 0 22 26 1 0 0 0 0 22 29 2 0 0 0 0 23 45 2 0 0 0 0 23 57 1 0 0 0 0 24 30 1 0 0 0 0 25 36 1 0 0 0 0 26 55 1 1 0 0 0 27 41 1 1 0 0 0 27 46 1 0 0 0 0 28 42 1 1 0 0 0 28 54 1 0 0 0 0 29 31 1 0 0 0 0 29 40 1 0 0 0 0 30 32 1 0 0 0 0 30 44 1 6 0 0 0 31 34 1 0 0 0 0 31 47 1 1 0 0 0 32 37 1 6 0 0 0 32 48 1 0 0 0 0 33 35 1 0 0 0 0 33 41 1 1 0 0 0 33 42 1 0 0 0 0 34 41 1 0 0 0 0 34 49 2 0 0 0 0 35 43 1 6 0 0 0 35 56 1 0 0 0 0 36 50 2 0 0 0 0 36 56 1 0 0 0 0 37 51 2 0 0 0 0 37 55 1 0 0 0 0 38 44 2 3 0 0 0 38 52 1 0 0 0 0 38 58 1 0 0 0 0 39 58 1 0 0 0 0 40 43 1 0 0 0 0 41 8 1 1 0 0 0 42 57 1 6 0 0 0 43 53 1 6 0 0 0 46 59 1 0 0 0 0 47 60 1 0 0 0 0 48 61 1 0 0 0 0 52 62 1 0 0 0 0 53 63 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000590
DrugBank	DB01248
ChEMBL	CHEMBL92
IUPHAR/BPS	6809
PharmaGKB	PA449383
KEGG Drug	D02165
PubChem CID	148124
ChEBI	4672
CAS Number	114977-28-5

Drug Properties

Molecular Weight	807.35
ALogP	-0.4179
MLogP	4.54
XLogP	5.05
HDA	15
HBD	5
Rotatable Bonds	26
TPSA	227.94
RO5 Violation	3