NPASS drugs

Drug Information

Drug ID:	NPD8462
Drug Name:	simotaxel
Molecular Formula:	C46H57NO15S
Canonical SMILES:	CC(OC(=N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@@]4(CO[C@@H]4C[C@@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C1CCCC1)C)O)OC(=O)C)O)c1cccs1)O)C
Standard InCHI:	InChI=1S/C46H57NO15S/c1-23(2)58-42(55)47-33(29-18-13-19-63-29)34(50)41(54)59-28-21-46(56)38(61-40(53)27-14-9-8-10-15-27)36-44(7,30(49)20-31-45(36,22-57-31)62-25(4)48)37(51)35(32(24(28)3)43(46,5)6)60-39(52)26-16-11-12-17-26/h8-10,13-15,18-19,23,26,28,30-31,33-36,38,49-50,56H,11-12,16-17,20-22H2,1-7H3,(H,47,55)/t28-,30-,31+,33-,34+,35+,36-,38-,44+,45-,46+/m0/s1
Standard InCHIKey:	SLGIWUWTSWJBQE-VLCCYYTCSA-N
Max Developmental Stage:	Phase 1
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD8462

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	211
0.1-0.2	998
0.2-0.3	2191
0.3-0.4	5698
0.4-0.5	10705
0.5-0.6	9675
0.6-0.7	1282
0.7-0.8	101
0.8-0.85	28
0.85-0.9	1
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	0.8737	NPC471623
Intermediate Similarity	0.8497	NPC324251
Intermediate Similarity	0.8497	NPC275170
Intermediate Similarity	0.8497	NPC306001
Intermediate Similarity	0.8497	NPC473400
Intermediate Similarity	0.8497	NPC206211
Intermediate Similarity	0.8497	NPC471629
Intermediate Similarity	0.8454	NPC67246
Intermediate Similarity	0.8454	NPC33372
Intermediate Similarity	0.8402	NPC471754
Intermediate Similarity	0.8402	NPC473300
Intermediate Similarity	0.8402	NPC475336
Intermediate Similarity	0.8402	NPC453583
Intermediate Similarity	0.8402	NPC317882
Intermediate Similarity	0.83	NPC472391
Intermediate Similarity	0.8283	NPC208553
Intermediate Similarity	0.8283	NPC181964
Intermediate Similarity	0.8283	NPC471606
Intermediate Similarity	0.825	NPC472392
Intermediate Similarity	0.825	NPC472375
Intermediate Similarity	0.8241	NPC473558
Intermediate Similarity	0.8232	NPC191193
Intermediate Similarity	0.8232	NPC215892
Intermediate Similarity	0.8232	NPC321072
Intermediate Similarity	0.8232	NPC242662
Intermediate Similarity	0.8177	NPC116862
Intermediate Similarity	0.815	NPC473490
Intermediate Similarity	0.8128	NPC289383
Intermediate Similarity	0.81	NPC36607
Intermediate Similarity	0.7929	NPC327699
Intermediate Similarity	0.7606	NPC219419
Intermediate Similarity	0.7566	NPC259144
Intermediate Similarity	0.7566	NPC155329
Intermediate Similarity	0.7566	NPC114357
Intermediate Similarity	0.7526	NPC471493
Intermediate Similarity	0.7513	NPC134685
Intermediate Similarity	0.7513	NPC248265
Intermediate Similarity	0.7513	NPC11588
Intermediate Similarity	0.7513	NPC229545
Intermediate Similarity	0.7487	NPC472393
Intermediate Similarity	0.7474	NPC473670
Intermediate Similarity	0.7474	NPC21410
Intermediate Similarity	0.7447	NPC91730
Intermediate Similarity	0.7435	NPC106895
Intermediate Similarity	0.7435	NPC217091
Intermediate Similarity	0.7407	NPC51602
Intermediate Similarity	0.7407	NPC197037
Intermediate Similarity	0.7407	NPC471103
Intermediate Similarity	0.7382	NPC282239
Intermediate Similarity	0.734	NPC217918
Intermediate Similarity	0.7292	NPC472549
Intermediate Similarity	0.7268	NPC471102
Intermediate Similarity	0.7208	NPC66193
Intermediate Similarity	0.7202	NPC228204
Intermediate Similarity	0.7202	NPC26033
Intermediate Similarity	0.7188	NPC472548
Intermediate Similarity	0.7179	NPC469399
Intermediate Similarity	0.7173	NPC470245
Intermediate Similarity	0.7173	NPC473214
Intermediate Similarity	0.7173	NPC7095
Intermediate Similarity	0.7173	NPC254558
Intermediate Similarity	0.7172	NPC471134
Intermediate Similarity	0.7157	NPC55744
Intermediate Similarity	0.7157	NPC43304
Intermediate Similarity	0.7157	NPC477190
Intermediate Similarity	0.7157	NPC477188
Intermediate Similarity	0.715	NPC1173
Intermediate Similarity	0.715	NPC242262
Intermediate Similarity	0.715	NPC102465
Intermediate Similarity	0.715	NPC304876
Intermediate Similarity	0.715	NPC472005
Intermediate Similarity	0.715	NPC40138
Intermediate Similarity	0.715	NPC256142
Intermediate Similarity	0.715	NPC472030
Intermediate Similarity	0.715	NPC237549
Intermediate Similarity	0.715	NPC133430
Intermediate Similarity	0.715	NPC257213
Intermediate Similarity	0.715	NPC472022
Intermediate Similarity	0.715	NPC158333
Intermediate Similarity	0.715	NPC249471
Intermediate Similarity	0.715	NPC469477
Intermediate Similarity	0.715	NPC473414
Intermediate Similarity	0.715	NPC265395
Intermediate Similarity	0.7143	NPC127857
Intermediate Similarity	0.7143	NPC301946
Intermediate Similarity	0.7143	NPC277053
Intermediate Similarity	0.7143	NPC471100
Intermediate Similarity	0.7143	NPC471107
Intermediate Similarity	0.7136	NPC61891
Intermediate Similarity	0.7135	NPC306799
Intermediate Similarity	0.7135	NPC470153
Intermediate Similarity	0.7135	NPC101043
Intermediate Similarity	0.7128	NPC469417
Intermediate Similarity	0.712	NPC60509
Intermediate Similarity	0.712	NPC81698
Intermediate Similarity	0.712	NPC250046
Intermediate Similarity	0.712	NPC473215
Intermediate Similarity	0.712	NPC476975
Intermediate Similarity	0.7113	NPC112523
Intermediate Similarity	0.7113	NPC114410
Intermediate Similarity	0.7105	NPC477737
Intermediate Similarity	0.7105	NPC474935
Intermediate Similarity	0.7098	NPC477905
Intermediate Similarity	0.709	NPC471912
Intermediate Similarity	0.709	NPC80895
Intermediate Similarity	0.709	NPC38696
Intermediate Similarity	0.7083	NPC165260
Intermediate Similarity	0.7083	NPC198455
Intermediate Similarity	0.7083	NPC161239
Intermediate Similarity	0.7083	NPC112216
Intermediate Similarity	0.7074	NPC34012
Intermediate Similarity	0.7062	NPC77719
Intermediate Similarity	0.705	NPC324769
Intermediate Similarity	0.705	NPC325732
Intermediate Similarity	0.7041	NPC469771
Intermediate Similarity	0.7035	NPC329960
Intermediate Similarity	0.7035	NPC295408
Intermediate Similarity	0.7035	NPC322420
Intermediate Similarity	0.7035	NPC150893
Intermediate Similarity	0.703	NPC477469
Intermediate Similarity	0.703	NPC477473
Intermediate Similarity	0.703	NPC477466
Intermediate Similarity	0.703	NPC477471
Intermediate Similarity	0.7026	NPC5115
Intermediate Similarity	0.7026	NPC469730
Intermediate Similarity	0.7026	NPC473632
Intermediate Similarity	0.7026	NPC473611
Intermediate Similarity	0.7026	NPC132599
Intermediate Similarity	0.701	NPC469421
Intermediate Similarity	0.7005	NPC49297
Remote Similarity	0.699	NPC70344
Remote Similarity	0.699	NPC11410
Remote Similarity	0.6985	NPC275477
Remote Similarity	0.6984	NPC182869
Remote Similarity	0.6984	NPC472546
Remote Similarity	0.698	NPC469420
Remote Similarity	0.6963	NPC472568
Remote Similarity	0.6963	NPC476973
Remote Similarity	0.6963	NPC469349
Remote Similarity	0.6963	NPC472575
Remote Similarity	0.6963	NPC200471
Remote Similarity	0.6963	NPC96903
Remote Similarity	0.6963	NPC470159
Remote Similarity	0.6963	NPC174982
Remote Similarity	0.6963	NPC70403
Remote Similarity	0.6963	NPC158663
Remote Similarity	0.6963	NPC177940
Remote Similarity	0.6963	NPC171525
Remote Similarity	0.6963	NPC184817
Remote Similarity	0.6963	NPC473088
Remote Similarity	0.6963	NPC472571
Remote Similarity	0.6963	NPC29704
Remote Similarity	0.6963	NPC470157
Remote Similarity	0.6963	NPC472572
Remote Similarity	0.6963	NPC471104
Remote Similarity	0.6954	NPC477735
Remote Similarity	0.6954	NPC181924
Remote Similarity	0.6952	NPC209865
Remote Similarity	0.695	NPC478073
Remote Similarity	0.6939	NPC251139
Remote Similarity	0.6939	NPC34066
Remote Similarity	0.6939	NPC469422
Remote Similarity	0.6935	NPC476077
Remote Similarity	0.6931	NPC97947
Remote Similarity	0.6931	NPC472576
Remote Similarity	0.6931	NPC118080
Remote Similarity	0.6931	NPC291599
Remote Similarity	0.6931	NPC41481
Remote Similarity	0.6931	NPC16912
Remote Similarity	0.6931	NPC27377
Remote Similarity	0.6931	NPC87448
Remote Similarity	0.6927	NPC469513
Remote Similarity	0.6927	NPC94602
Remote Similarity	0.6919	NPC477736
Remote Similarity	0.6911	NPC241951
Remote Similarity	0.6911	NPC188865
Remote Similarity	0.6911	NPC70716
Remote Similarity	0.6911	NPC475122
Remote Similarity	0.6911	NPC95265
Remote Similarity	0.6911	NPC472573
Remote Similarity	0.6911	NPC476974
Remote Similarity	0.6911	NPC57628
Remote Similarity	0.6911	NPC472570
Remote Similarity	0.6911	NPC125106
Remote Similarity	0.6911	NPC470231
Remote Similarity	0.6911	NPC163719
Remote Similarity	0.6911	NPC11685
Remote Similarity	0.6911	NPC475759
Remote Similarity	0.6911	NPC25768
Remote Similarity	0.6911	NPC470152
Remote Similarity	0.6911	NPC95810
Remote Similarity	0.6911	NPC472569
Remote Similarity	0.69	NPC253738
Remote Similarity	0.6884	NPC477623
Remote Similarity	0.6881	NPC30171
Remote Similarity	0.6878	NPC472547
Remote Similarity	0.6878	NPC171207
Remote Similarity	0.6878	NPC100913
Remote Similarity	0.6878	NPC90614
Remote Similarity	0.6878	NPC275592

Drug Structure

NPD8462 OpenBabel08211713022D 67 73 0 0 1 0 0 0 0 0999 V2000 -6.4129 5.6279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3742 4.3751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0514 -0.5467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9340 -1.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4451 -3.0854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5412 -3.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 -0.8423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1227 -3.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7738 -2.1695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5677 -3.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0676 -3.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9099 -3.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5640 -0.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8699 -2.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6638 -3.6162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1392 -2.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5021 -3.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6551 0.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9129 0.7865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7896 1.3676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0795 -1.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5319 4.7240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 -1.2033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0534 -2.1700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0257 -2.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3149 -2.7738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7067 -0.9689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4423 0.9022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5791 0.9117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9117 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6797 -1.9062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6000 1.2511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8766 0.6961 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9156 -1.0255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7896 -0.4559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4598 -0.2360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5536 -1.3365 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3746 -1.6298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4110 -2.6548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0343 1.0450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2043 2.7101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8901 -2.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5791 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 -1.0095 -2.1261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4809 2.1550 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5815 -3.9313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3687 1.3676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9956 -0.2078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0148 0.4873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2785 -1.5108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8559 -3.3781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9153 1.9489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0466 2.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6852 -2.9782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 0.9117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0853 3.6140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5877 -0.0650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8196 -0.9065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0621 -1.8125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2360 -0.8806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2196 1.3786 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -2.3687 2.2793 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8380 -0.5567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7699 2.9162 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2609 -3.6851 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 43 1 0 0 0 0 6 43 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 19 2 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 26 1 0 0 0 0 17 26 1 0 0 0 0 18 29 2 0 0 0 0 19 63 1 0 0 0 0 20 30 1 0 0 0 0 20 31 1 0 0 0 0 21 28 1 0 0 0 0 21 46 1 0 0 0 0 22 45 1 0 0 0 0 22 57 1 0 0 0 0 23 58 1 0 0 0 0 24 28 1 0 0 0 0 24 32 2 0 0 0 0 25 48 2 0 0 0 0 25 62 1 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 28 59 1 1 0 0 0 29 33 1 0 0 0 0 29 63 1 0 0 0 0 30 44 1 1 0 0 0 30 49 1 0 0 0 0 31 45 1 1 0 0 0 31 57 1 0 0 0 0 32 35 1 0 0 0 0 32 43 1 0 0 0 0 33 34 1 0 0 0 0 33 47 1 6 0 0 0 34 41 1 6 0 0 0 34 50 1 0 0 0 0 35 37 1 0 0 0 0 35 60 1 1 0 0 0 36 38 1 0 0 0 0 36 44 1 1 0 0 0 36 45 1 0 0 0 0 37 44 1 0 0 0 0 37 51 2 0 0 0 0 38 46 1 6 0 0 0 38 61 1 0 0 0 0 39 52 2 0 0 0 0 39 60 1 0 0 0 0 40 53 2 0 0 0 0 40 61 1 0 0 0 0 41 54 2 0 0 0 0 41 59 1 0 0 0 0 42 47 2 3 0 0 0 42 55 1 0 0 0 0 42 58 1 0 0 0 0 43 46 1 0 0 0 0 44 7 1 1 0 0 0 45 62 1 6 0 0 0 46 56 1 6 0 0 0 49 64 1 0 0 0 0 50 65 1 0 0 0 0 55 66 1 0 0 0 0 56 67 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB005909
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	895.34
ALogP	-0.649
MLogP	4.65
XLogP	4.978
HDA	16
HBD	4
Rotatable Bonds	27
TPSA	262.25
RO5 Violation	2