NPASS drugs

Drug Information

Drug ID:	NPD7781
Drug Name:	Ergotamine
Molecular Formula:	C33H35N5O5
Canonical SMILES:	OC(=N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3
Standard InCHI:	InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1
Standard InCHIKey:	XCGSFFUVFURLIX-VFGNJEKYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD7781

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	329
0.1-0.2	1815
0.2-0.3	11074
0.3-0.4	12911
0.4-0.5	1822
0.5-0.6	1592
0.6-0.7	1108
0.7-0.8	225
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	3

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	1.0	NPC56109
High Similarity	1.0	NPC191382
High Similarity	0.9752	NPC155444
Intermediate Similarity	0.8458	NPC477714
Intermediate Similarity	0.8326	NPC477715
Intermediate Similarity	0.8318	NPC478157
Intermediate Similarity	0.8255	NPC162860
Intermediate Similarity	0.8255	NPC478158
Intermediate Similarity	0.8246	NPC54420
Intermediate Similarity	0.8213	NPC171317
Intermediate Similarity	0.8128	NPC17059
Intermediate Similarity	0.8119	NPC281049
Intermediate Similarity	0.8056	NPC75634
Intermediate Similarity	0.8	NPC213629
Intermediate Similarity	0.799	NPC94752
Intermediate Similarity	0.798	NPC228835
Intermediate Similarity	0.7917	NPC107077
Intermediate Similarity	0.7917	NPC223791
Intermediate Similarity	0.786	NPC325976
Intermediate Similarity	0.7854	NPC54744
Intermediate Similarity	0.784	NPC475506
Intermediate Similarity	0.783	NPC293917
Intermediate Similarity	0.7814	NPC473376
Intermediate Similarity	0.7807	NPC475969
Intermediate Similarity	0.7807	NPC475859
Intermediate Similarity	0.7804	NPC155143
Intermediate Similarity	0.7783	NPC473640
Intermediate Similarity	0.7783	NPC11126
Intermediate Similarity	0.7763	NPC477175
Intermediate Similarity	0.7763	NPC326363
Intermediate Similarity	0.7763	NPC470730
Intermediate Similarity	0.7753	NPC476491
Intermediate Similarity	0.7745	NPC91179
Intermediate Similarity	0.7739	NPC323752
Intermediate Similarity	0.7729	NPC474877
Intermediate Similarity	0.7727	NPC31385
Intermediate Similarity	0.7727	NPC75726
Intermediate Similarity	0.7727	NPC110602
Intermediate Similarity	0.7721	NPC193761
Intermediate Similarity	0.7703	NPC470731
Intermediate Similarity	0.7696	NPC89987
Intermediate Similarity	0.7696	NPC165743
Intermediate Similarity	0.7686	NPC477176
Intermediate Similarity	0.7686	NPC470729
Intermediate Similarity	0.7682	NPC478029
Intermediate Similarity	0.7667	NPC473763
Intermediate Similarity	0.7667	NPC117244
Intermediate Similarity	0.7664	NPC100321
Intermediate Similarity	0.7662	NPC63279
Intermediate Similarity	0.7654	NPC472846
Intermediate Similarity	0.7652	NPC477177
Intermediate Similarity	0.7639	NPC476874
Intermediate Similarity	0.7632	NPC319232
Intermediate Similarity	0.7632	NPC909
Intermediate Similarity	0.7632	NPC24370
Intermediate Similarity	0.7632	NPC475338
Intermediate Similarity	0.7629	NPC297642
Intermediate Similarity	0.7623	NPC470732
Intermediate Similarity	0.7621	NPC64216
Intermediate Similarity	0.7613	NPC475602
Intermediate Similarity	0.7598	NPC475258
Intermediate Similarity	0.7597	NPC478028
Intermediate Similarity	0.7574	NPC194411
Intermediate Similarity	0.7571	NPC321708
Intermediate Similarity	0.7561	NPC68354
Intermediate Similarity	0.756	NPC235684
Intermediate Similarity	0.7556	NPC473310
Intermediate Similarity	0.754	NPC478009
Intermediate Similarity	0.754	NPC478010
Intermediate Similarity	0.7523	NPC320968
Intermediate Similarity	0.7512	NPC308931
Intermediate Similarity	0.7512	NPC99939
Intermediate Similarity	0.75	NPC315467
Intermediate Similarity	0.7489	NPC471193
Intermediate Similarity	0.7489	NPC6865
Intermediate Similarity	0.7489	NPC471194
Intermediate Similarity	0.7489	NPC153980
Intermediate Similarity	0.7477	NPC475422
Intermediate Similarity	0.7466	NPC87755
Intermediate Similarity	0.7465	NPC47190
Intermediate Similarity	0.7464	NPC165495
Intermediate Similarity	0.7463	NPC37423
Intermediate Similarity	0.7463	NPC275305
Intermediate Similarity	0.7456	NPC474896
Intermediate Similarity	0.7453	NPC95783
Intermediate Similarity	0.7449	NPC314882
Intermediate Similarity	0.7444	NPC72956
Intermediate Similarity	0.7435	NPC19170
Intermediate Similarity	0.7429	NPC15102
Intermediate Similarity	0.7426	NPC472207
Intermediate Similarity	0.7424	NPC312942
Intermediate Similarity	0.7424	NPC31097
Intermediate Similarity	0.7424	NPC327095
Intermediate Similarity	0.7414	NPC297862
Intermediate Similarity	0.7412	NPC272174
Intermediate Similarity	0.7407	NPC227582
Intermediate Similarity	0.7403	NPC472762
Intermediate Similarity	0.7398	NPC478006
Intermediate Similarity	0.7397	NPC476073
Intermediate Similarity	0.7393	NPC63031
Intermediate Similarity	0.7391	NPC59269
Intermediate Similarity	0.7391	NPC40455
Intermediate Similarity	0.7389	NPC472027
Intermediate Similarity	0.7385	NPC252338
Intermediate Similarity	0.7382	NPC69843
Intermediate Similarity	0.7378	NPC473757
Intermediate Similarity	0.7356	NPC126709
Intermediate Similarity	0.7356	NPC248041
Intermediate Similarity	0.7356	NPC283219
Intermediate Similarity	0.7352	NPC300183
Intermediate Similarity	0.7348	NPC253987
Intermediate Similarity	0.7342	NPC477065
Intermediate Similarity	0.7339	NPC74413
Intermediate Similarity	0.7336	NPC153400
Intermediate Similarity	0.733	NPC161861
Intermediate Similarity	0.7321	NPC126066
Intermediate Similarity	0.7315	NPC294693
Intermediate Similarity	0.7313	NPC471192
Intermediate Similarity	0.7308	NPC145885
Intermediate Similarity	0.7308	NPC84827
Intermediate Similarity	0.7308	NPC14113
Intermediate Similarity	0.7306	NPC470497
Intermediate Similarity	0.7304	NPC471506
Intermediate Similarity	0.7295	NPC469938
Intermediate Similarity	0.7294	NPC470499
Intermediate Similarity	0.7285	NPC317701
Intermediate Similarity	0.7284	NPC474196
Intermediate Similarity	0.7273	NPC215795
Intermediate Similarity	0.7273	NPC176199
Intermediate Similarity	0.7273	NPC213468
Intermediate Similarity	0.7269	NPC184225
Intermediate Similarity	0.7268	NPC63751
Intermediate Similarity	0.7265	NPC166492
Intermediate Similarity	0.7265	NPC473362
Intermediate Similarity	0.726	NPC267885
Intermediate Similarity	0.7255	NPC478012
Intermediate Similarity	0.7255	NPC478011
Intermediate Similarity	0.7251	NPC470205
Intermediate Similarity	0.7246	NPC314603
Intermediate Similarity	0.7241	NPC476817
Intermediate Similarity	0.724	NPC260900
Intermediate Similarity	0.7237	NPC472845
Intermediate Similarity	0.7227	NPC314176
Intermediate Similarity	0.7225	NPC229348
Intermediate Similarity	0.7224	NPC14812
Intermediate Similarity	0.722	NPC49954
Intermediate Similarity	0.722	NPC474561
Intermediate Similarity	0.722	NPC160105
Intermediate Similarity	0.7215	NPC265576
Intermediate Similarity	0.7212	NPC203468
Intermediate Similarity	0.7212	NPC149155
Intermediate Similarity	0.7212	NPC82370
Intermediate Similarity	0.7212	NPC110500
Intermediate Similarity	0.7197	NPC28945
Intermediate Similarity	0.719	NPC477107
Intermediate Similarity	0.719	NPC219336
Intermediate Similarity	0.719	NPC477108
Intermediate Similarity	0.719	NPC477109
Intermediate Similarity	0.7188	NPC323927
Intermediate Similarity	0.7186	NPC474195
Intermediate Similarity	0.7174	NPC475736
Intermediate Similarity	0.7162	NPC36405
Intermediate Similarity	0.7162	NPC251936
Intermediate Similarity	0.7156	NPC195239
Intermediate Similarity	0.7156	NPC157828
Intermediate Similarity	0.7156	NPC469896
Intermediate Similarity	0.7149	NPC17487
Intermediate Similarity	0.7149	NPC476492
Intermediate Similarity	0.7149	NPC201831
Intermediate Similarity	0.7143	NPC206819
Intermediate Similarity	0.7143	NPC217372
Intermediate Similarity	0.7143	NPC323198
Intermediate Similarity	0.7143	NPC15573
Intermediate Similarity	0.7143	NPC318065
Intermediate Similarity	0.7143	NPC70155
Intermediate Similarity	0.7143	NPC183662
Intermediate Similarity	0.7143	NPC56765
Intermediate Similarity	0.7136	NPC472294
Intermediate Similarity	0.7136	NPC131887
Intermediate Similarity	0.7125	NPC285343
Intermediate Similarity	0.7123	NPC11445
Intermediate Similarity	0.7119	NPC33949
Intermediate Similarity	0.7118	NPC313640
Intermediate Similarity	0.7118	NPC250835
Intermediate Similarity	0.7115	NPC242872
Intermediate Similarity	0.7115	NPC125181
Intermediate Similarity	0.7115	NPC314056
Intermediate Similarity	0.7115	NPC263117
Intermediate Similarity	0.7111	NPC225821
Intermediate Similarity	0.71	NPC174788
Intermediate Similarity	0.7097	NPC476460
Intermediate Similarity	0.7095	NPC41679
Intermediate Similarity	0.7082	NPC2395
Intermediate Similarity	0.708	NPC258062
Intermediate Similarity	0.708	NPC314957
Intermediate Similarity	0.7073	NPC282231
Intermediate Similarity	0.7072	NPC49196
Intermediate Similarity	0.7072	NPC195461
Intermediate Similarity	0.7072	NPC249150
Intermediate Similarity	0.7072	NPC79129

Drug Structure

NPD7781 OpenBabel08211712032D 46 53 0 0 1 0 0 0 0 0999 V2000 1.0847 -0.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1581 3.5225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 5.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1643 5.5111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3773 4.2975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6047 -0.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2157 -0.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4637 4.8108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6767 3.5972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7894 -0.2921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4198 -0.2921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2373 -0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3709 0.5331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0192 3.1535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1588 0.6489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7889 2.5321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4196 2.5322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3431 2.0610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7198 3.8538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6045 2.0615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3433 1.1195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7893 0.6491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9740 1.1199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4199 0.6496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9738 2.0613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2754 2.1966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7877 0.2827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6045 1.1199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4855 0.6240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2322 1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4145 1.5483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7697 0.6236 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8309 0.5393 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2350 1.1203 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6275 1.1191 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1583 2.5319 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4884 0.9831 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5748 1.4963 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4858 -0.3666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9328 2.6403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9538 2.3793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4542 -0.2307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1874 0.8652 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6280 -0.8621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0990 -1.1554 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 36 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 11 24 2 0 0 0 0 12 27 1 0 0 0 0 13 37 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 15 23 2 0 0 0 0 16 20 1 0 0 0 0 17 20 2 0 0 0 0 17 34 1 0 0 0 0 18 21 1 0 0 0 0 18 36 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 28 2 0 0 0 0 23 25 1 0 0 0 0 24 28 1 0 0 0 0 24 34 1 0 0 0 0 25 16 1 6 0 0 0 25 36 1 0 0 0 0 26 14 1 6 0 0 0 26 30 1 0 0 0 0 26 38 1 0 0 0 0 27 33 1 6 0 0 0 27 37 1 0 0 0 0 29 35 2 3 0 0 0 29 39 1 0 0 0 0 30 37 1 0 0 0 0 30 40 2 0 0 0 0 31 32 1 0 0 0 0 31 38 1 0 0 0 0 31 41 2 0 0 0 0 32 1 1 1 0 0 0 32 35 1 0 0 0 0 32 43 1 0 0 0 0 33 38 1 0 0 0 0 33 42 1 6 0 0 0 33 43 1 0 0 0 0 34 44 1 0 0 0 0 39 45 1 0 0 0 0 42 46 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000141
DrugBank	DB00696
ChEMBL	CHEMBL442
IUPHAR/BPS	149
PharmaGKB	PA164747651
KEGG Drug
PubChem CID	8223
ChEBI	64318
CAS Number	113-15-5

Drug Properties

Molecular Weight	581.26
ALogP	-1.9682
MLogP	3.99
XLogP	4.003
HDA	10
HBD	3
Rotatable Bonds	8
TPSA	121.7
RO5 Violation	0