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:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD7781

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	97304
0.1-0.2	110098
0.2-0.3	4173
0.3-0.4	75
0.4-0.5	19
0.5-0.6	29
0.6-0.7	24
0.7-0.8	9
0.8-0.85	3
0.85-0.9	3
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	NPC273359
High Similarity	1.0	NPC191382
High Similarity	0.8969	NPC56109
High Similarity	0.8969	NPC306412
High Similarity	0.8969	NPC203217
Intermediate Similarity	0.8454	NPC58642
Intermediate Similarity	0.8454	NPC49336
Intermediate Similarity	0.8454	NPC249875
Intermediate Similarity	0.7549	NPC155444
Intermediate Similarity	0.7549	NPC224542
Intermediate Similarity	0.7549	NPC137993
Intermediate Similarity	0.7196	NPC230554
Intermediate Similarity	0.7103	NPC320236
Intermediate Similarity	0.7103	NPC571033
Intermediate Similarity	0.7103	NPC609531
Intermediate Similarity	0.7037	NPC510017
Intermediate Similarity	0.7037	NPC511922
Remote Similarity	0.6296	NPC526488
Remote Similarity	0.6182	NPC491494
Remote Similarity	0.614	NPC534269
Remote Similarity	0.6091	NPC562624
Remote Similarity	0.6091	NPC593275
Remote Similarity	0.6036	NPC225644
Remote Similarity	0.6036	NPC329078
Remote Similarity	0.6036	NPC315681
Remote Similarity	0.6036	NPC326189
Remote Similarity	0.6036	NPC511970
Remote Similarity	0.6036	NPC513877
Remote Similarity	0.6036	NPC536533
Remote Similarity	0.6036	NPC543983
Remote Similarity	0.6036	NPC545985
Remote Similarity	0.6036	NPC557179
Remote Similarity	0.6036	NPC586782
Remote Similarity	0.6036	NPC596345
Remote Similarity	0.6036	NPC603739
Remote Similarity	0.6036	NPC607491
Remote Similarity	0.6018	NPC24441
Remote Similarity	0.6018	NPC284772
Remote Similarity	0.6018	NPC194808
Remote Similarity	0.6018	NPC127711
Remote Similarity	0.6	NPC116551
Remote Similarity	0.5982	NPC492903
Remote Similarity	0.5982	NPC564493
Remote Similarity	0.5929	NPC510468
Remote Similarity	0.5929	NPC528454
Remote Similarity	0.5929	NPC572386
Remote Similarity	0.5826	NPC503543
Remote Similarity	0.5657	NPC68354
Remote Similarity	0.5657	NPC285055
Remote Similarity	0.5566	NPC46468
Remote Similarity	0.5426	NPC570281
Remote Similarity	0.5354	NPC558145
Remote Similarity	0.5354	NPC572522
Remote Similarity	0.534	NPC526211
Remote Similarity	0.534	NPC611966
Remote Similarity	0.5299	NPC560415
Remote Similarity	0.5243	NPC269208
Remote Similarity	0.5221	NPC574684
Remote Similarity	0.5221	NPC598588
Remote Similarity	0.521	NPC573018
Remote Similarity	0.5175	NPC562073
Remote Similarity	0.5175	NPC570644
Remote Similarity	0.5161	NPC557604
Remote Similarity	0.5152	NPC313654
Remote Similarity	0.5146	NPC325904
Remote Similarity	0.5146	NPC520778
Remote Similarity	0.5146	NPC593969
Remote Similarity	0.5146	NPC604662
Remote Similarity	0.5126	NPC572406
Remote Similarity	0.5083	NPC570156

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