NPASS drugs

Drug Information

Drug ID:	NPD5270
Drug Name:	avitriptan
Molecular Formula:	C22H30N6O3S
Canonical SMILES:	COc1cncnc1N1CCN(CC1)CCCc1c[nH]c2c1cc(cc2)CS(=O)(=O)NC
Standard InCHI:	InChI=1S/C22H30N6O3S/c1-23-32(29,30)15-17-5-6-20-19(12-17)18(13-25-20)4-3-7-27-8-10-28(11-9-27)22-21(31-2)14-24-16-26-22/h5-6,12-14,16,23,25H,3-4,7-11,15H2,1-2H3
Standard InCHIKey:	WRZVGHXUPBWIOO-UHFFFAOYSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5270

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	644
0.1-0.2	9672
0.2-0.3	13823
0.3-0.4	3179
0.4-0.5	1674
0.5-0.6	1175
0.6-0.7	714
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
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
Intermediate Similarity	0.7383	NPC469308
Intermediate Similarity	0.7273	NPC470203
Intermediate Similarity	0.7241	NPC317054
Intermediate Similarity	0.7222	NPC470204
Intermediate Similarity	0.7118	NPC130570
Intermediate Similarity	0.7079	NPC49217
Intermediate Similarity	0.705	NPC122141
Intermediate Similarity	0.702	NPC476219
Intermediate Similarity	0.7019	NPC16659
Remote Similarity	0.6983	NPC132631
Remote Similarity	0.6983	NPC103687
Remote Similarity	0.6971	NPC265710
Remote Similarity	0.6951	NPC116555
Remote Similarity	0.6941	NPC19872
Remote Similarity	0.6927	NPC265576
Remote Similarity	0.6919	NPC470233
Remote Similarity	0.6904	NPC30540
Remote Similarity	0.6904	NPC321911
Remote Similarity	0.6897	NPC317105
Remote Similarity	0.6888	NPC39092
Remote Similarity	0.6886	NPC470731
Remote Similarity	0.6884	NPC325903
Remote Similarity	0.6881	NPC44773
Remote Similarity	0.6881	NPC215584
Remote Similarity	0.6856	NPC267811
Remote Similarity	0.6853	NPC179787
Remote Similarity	0.6853	NPC201380
Remote Similarity	0.6853	NPC469811
Remote Similarity	0.6851	NPC314954
Remote Similarity	0.6842	NPC473380
Remote Similarity	0.6842	NPC240088
Remote Similarity	0.6837	NPC204141
Remote Similarity	0.6832	NPC56765
Remote Similarity	0.6828	NPC471603
Remote Similarity	0.6825	NPC307191
Remote Similarity	0.6814	NPC90723
Remote Similarity	0.6807	NPC180504
Remote Similarity	0.6802	NPC143872
Remote Similarity	0.6802	NPC63545
Remote Similarity	0.68	NPC200214
Remote Similarity	0.6794	NPC280852
Remote Similarity	0.6786	NPC475288
Remote Similarity	0.6784	NPC40070
Remote Similarity	0.6776	NPC474707
Remote Similarity	0.6771	NPC476138
Remote Similarity	0.6771	NPC245816
Remote Similarity	0.6768	NPC471957
Remote Similarity	0.6766	NPC476297
Remote Similarity	0.6765	NPC225018
Remote Similarity	0.6762	NPC68354
Remote Similarity	0.6761	NPC284678
Remote Similarity	0.6753	NPC110126
Remote Similarity	0.6753	NPC73767
Remote Similarity	0.6751	NPC314372
Remote Similarity	0.675	NPC216713
Remote Similarity	0.6744	NPC204565
Remote Similarity	0.6744	NPC317030
Remote Similarity	0.6739	NPC470732
Remote Similarity	0.6735	NPC190296
Remote Similarity	0.6732	NPC311276
Remote Similarity	0.6718	NPC469767
Remote Similarity	0.6718	NPC469779
Remote Similarity	0.6718	NPC469780
Remote Similarity	0.6718	NPC469784
Remote Similarity	0.6718	NPC469768
Remote Similarity	0.6718	NPC469783
Remote Similarity	0.6718	NPC469761
Remote Similarity	0.6713	NPC173028
Remote Similarity	0.6713	NPC65215
Remote Similarity	0.67	NPC24678
Remote Similarity	0.67	NPC236711
Remote Similarity	0.67	NPC53947
Remote Similarity	0.67	NPC105818
Remote Similarity	0.6695	NPC165743
Remote Similarity	0.6684	NPC469766
Remote Similarity	0.6683	NPC21605
Remote Similarity	0.6683	NPC194411
Remote Similarity	0.6682	NPC248454
Remote Similarity	0.668	NPC295452
Remote Similarity	0.668	NPC171393
Remote Similarity	0.6667	NPC300238
Remote Similarity	0.6667	NPC318065
Remote Similarity	0.6667	NPC88097
Remote Similarity	0.6667	NPC233936
Remote Similarity	0.6667	NPC474177
Remote Similarity	0.6667	NPC37423
Remote Similarity	0.6667	NPC471579
Remote Similarity	0.6667	NPC92796
Remote Similarity	0.6667	NPC472027
Remote Similarity	0.6667	NPC275305
Remote Similarity	0.6667	NPC470823
Remote Similarity	0.6667	NPC251936
Remote Similarity	0.6667	NPC135141
Remote Similarity	0.6667	NPC206819
Remote Similarity	0.6653	NPC316756
Remote Similarity	0.6652	NPC314957
Remote Similarity	0.6652	NPC477111
Remote Similarity	0.6651	NPC12649
Remote Similarity	0.6651	NPC15102
Remote Similarity	0.6651	NPC470498
Remote Similarity	0.6649	NPC105127
Remote Similarity	0.6649	NPC84911
Remote Similarity	0.6636	NPC163055
Remote Similarity	0.6636	NPC103119
Remote Similarity	0.6636	NPC133366
Remote Similarity	0.6636	NPC294693
Remote Similarity	0.6635	NPC63751
Remote Similarity	0.6634	NPC469760
Remote Similarity	0.6634	NPC469763
Remote Similarity	0.6634	NPC73952
Remote Similarity	0.6634	NPC469786
Remote Similarity	0.6634	NPC469765
Remote Similarity	0.6634	NPC25008
Remote Similarity	0.6634	NPC259644
Remote Similarity	0.6633	NPC288838
Remote Similarity	0.6625	NPC469554
Remote Similarity	0.6625	NPC101543
Remote Similarity	0.662	NPC94752
Remote Similarity	0.6618	NPC469762
Remote Similarity	0.6611	NPC69843
Remote Similarity	0.6611	NPC470730
Remote Similarity	0.6611	NPC477175
Remote Similarity	0.6609	NPC75726
Remote Similarity	0.6609	NPC31385
Remote Similarity	0.6609	NPC26679
Remote Similarity	0.6609	NPC110602
Remote Similarity	0.6608	NPC473362
Remote Similarity	0.6608	NPC166492
Remote Similarity	0.6605	NPC108011
Remote Similarity	0.6604	NPC59269
Remote Similarity	0.6601	NPC75540
Remote Similarity	0.6601	NPC80597
Remote Similarity	0.6601	NPC211572
Remote Similarity	0.6601	NPC212376
Remote Similarity	0.6601	NPC70922
Remote Similarity	0.6598	NPC29886
Remote Similarity	0.6598	NPC96102
Remote Similarity	0.6598	NPC261195
Remote Similarity	0.6587	NPC49954
Remote Similarity	0.6587	NPC160105
Remote Similarity	0.6587	NPC474561
Remote Similarity	0.6585	NPC474880
Remote Similarity	0.6585	NPC221786
Remote Similarity	0.6585	NPC475990
Remote Similarity	0.6583	NPC159856
Remote Similarity	0.6583	NPC475859
Remote Similarity	0.6583	NPC475969
Remote Similarity	0.6582	NPC19170
Remote Similarity	0.658	NPC473757
Remote Similarity	0.658	NPC282247
Remote Similarity	0.6579	NPC66699
Remote Similarity	0.6577	NPC267928
Remote Similarity	0.6573	NPC215795
Remote Similarity	0.6573	NPC11126
Remote Similarity	0.6573	NPC176199
Remote Similarity	0.6571	NPC82331
Remote Similarity	0.657	NPC21174
Remote Similarity	0.657	NPC24802
Remote Similarity	0.657	NPC40779
Remote Similarity	0.657	NPC271797
Remote Similarity	0.657	NPC194640
Remote Similarity	0.6569	NPC469785
Remote Similarity	0.6568	NPC327095
Remote Similarity	0.6568	NPC312942
Remote Similarity	0.6565	NPC208284
Remote Similarity	0.6565	NPC54981
Remote Similarity	0.6564	NPC251722
Remote Similarity	0.6564	NPC477113
Remote Similarity	0.6564	NPC314102
Remote Similarity	0.656	NPC472289
Remote Similarity	0.6558	NPC48938
Remote Similarity	0.6557	NPC224764
Remote Similarity	0.6557	NPC474958
Remote Similarity	0.6553	NPC229173
Remote Similarity	0.655	NPC185782
Remote Similarity	0.6548	NPC115611
Remote Similarity	0.6546	NPC198988
Remote Similarity	0.6545	NPC324149
Remote Similarity	0.6544	NPC17273
Remote Similarity	0.6544	NPC135601
Remote Similarity	0.6544	NPC141612
Remote Similarity	0.654	NPC476817
Remote Similarity	0.654	NPC40455
Remote Similarity	0.6537	NPC94157
Remote Similarity	0.6537	NPC286427
Remote Similarity	0.6537	NPC469897
Remote Similarity	0.6537	NPC153980
Remote Similarity	0.6537	NPC216643
Remote Similarity	0.6537	NPC6865
Remote Similarity	0.6535	NPC175916
Remote Similarity	0.6535	NPC150447
Remote Similarity	0.653	NPC95783
Remote Similarity	0.653	NPC231536
Remote Similarity	0.6528	NPC467063
Remote Similarity	0.6528	NPC228835
Remote Similarity	0.6524	NPC91895
Remote Similarity	0.6524	NPC471192
Remote Similarity	0.6522	NPC167860
Remote Similarity	0.6522	NPC123976
Remote Similarity	0.6522	NPC282231

Drug Structure

NPD5270 OpenBabel08211706322D 34 37 0 0 0 0 0 0 0 0999 V2000 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9508 -2.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5798 -5.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2708 -4.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9107 -6.4155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 -6.9507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3764 -5.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7147 -6.7428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 -5.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2890 -4.4249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6492 -6.1191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3109 -4.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0019 -5.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9582 -5.1680 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -3.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6710 -6.3270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0674 -6.2076 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0237 -5.7918 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6418 -3.8896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3194 -2.9612 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 31 1 0 0 0 0 3 4 1 0 0 0 0 3 7 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 17 1 0 0 0 0 6 20 1 0 0 0 0 7 27 1 0 0 0 0 8 10 1 0 0 0 0 8 27 1 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 28 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 14 21 2 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 24 2 0 0 0 0 16 26 1 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 32 1 0 0 0 0 23 33 1 0 0 0 0 25 34 1 0 0 0 0 29 32 2 0 0 0 0 30 32 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB016206
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	458.21
ALogP	-1.436
MLogP	2.78
XLogP	1.033
HDA	8
HBD	2
Rotatable Bonds	11
TPSA	111.83
RO5 Violation	0