NPASS drugs

Drug Information

Drug ID:	NPD4075
Drug Name:	Lysergide
Molecular Formula:	C20H25N3O
Canonical SMILES:	CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
Standard InCHI:	"InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1"
Standard InCHIKey:	VAYOSLLFUXYJDT-RDTXWAMCSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4075

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	112728
0.1-0.2	95365
0.2-0.3	3382
0.3-0.4	152
0.4-0.5	22
0.5-0.6	70
0.6-0.7	18
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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
Intermediate Similarity	0.7377	NPC589958
Intermediate Similarity	0.7377	NPC606264
Intermediate Similarity	0.7188	NPC570281
Remote Similarity	0.6912	NPC313654
Remote Similarity	0.6769	NPC275305
Remote Similarity	0.6769	NPC37423
Remote Similarity	0.6769	NPC491234
Remote Similarity	0.6769	NPC577263
Remote Similarity	0.6714	NPC558145
Remote Similarity	0.6714	NPC572522
Remote Similarity	0.6622	NPC526211
Remote Similarity	0.6622	NPC611966
Remote Similarity	0.6567	NPC194411
Remote Similarity	0.6351	NPC325904
Remote Similarity	0.6351	NPC520778
Remote Similarity	0.6351	NPC593969
Remote Similarity	0.6351	NPC604662
Remote Similarity	0.6216	NPC68354
Remote Similarity	0.6216	NPC285055
Remote Similarity	0.6104	NPC504538
Remote Similarity	0.6053	NPC269208
Remote Similarity	0.593	NPC574684
Remote Similarity	0.593	NPC598588
Remote Similarity	0.5882	NPC90408
Remote Similarity	0.5882	NPC230660
Remote Similarity	0.5862	NPC562073
Remote Similarity	0.5862	NPC570644
Remote Similarity	0.5821	NPC567556
Remote Similarity	0.5821	NPC600946
Remote Similarity	0.5775	NPC508875
Remote Similarity	0.5775	NPC509923
Remote Similarity	0.5714	NPC57047
Remote Similarity	0.5714	NPC598241
Remote Similarity	0.5663	NPC46468
Remote Similarity	0.5604	NPC562624
Remote Similarity	0.5604	NPC593275
Remote Similarity	0.5595	NPC527833
Remote Similarity	0.5595	NPC545520
Remote Similarity	0.5595	NPC566122
Remote Similarity	0.5571	NPC113927
Remote Similarity	0.5571	NPC19757
Remote Similarity	0.5556	NPC585451
Remote Similarity	0.5543	NPC329078
Remote Similarity	0.5543	NPC491494
Remote Similarity	0.5543	NPC513877
Remote Similarity	0.5543	NPC536533
Remote Similarity	0.5543	NPC545985
Remote Similarity	0.5543	NPC586782
Remote Similarity	0.5543	NPC603739
Remote Similarity	0.5495	NPC526488
Remote Similarity	0.5484	NPC492903
Remote Similarity	0.5426	NPC528454
Remote Similarity	0.5426	NPC572386
Remote Similarity	0.5426	NPC572406
Remote Similarity	0.5376	NPC315681
Remote Similarity	0.5376	NPC326189
Remote Similarity	0.5376	NPC511970
Remote Similarity	0.5376	NPC543983
Remote Similarity	0.5376	NPC557179
Remote Similarity	0.5376	NPC596345
Remote Similarity	0.5376	NPC607491
Remote Similarity	0.5319	NPC155444
Remote Similarity	0.5319	NPC58642
Remote Similarity	0.5319	NPC224542
Remote Similarity	0.5319	NPC49336
Remote Similarity	0.5319	NPC137993
Remote Similarity	0.5319	NPC249875
Remote Similarity	0.5319	NPC564493
Remote Similarity	0.5263	NPC510468
Remote Similarity	0.5213	NPC225644
Remote Similarity	0.5208	NPC24441
Remote Similarity	0.5208	NPC284772
Remote Similarity	0.5208	NPC194808
Remote Similarity	0.5208	NPC127711
Remote Similarity	0.5208	NPC570156
Remote Similarity	0.5155	NPC503543
Remote Similarity	0.5102	NPC320236
Remote Similarity	0.5102	NPC571033
Remote Similarity	0.5102	NPC609531
Remote Similarity	0.507	NPC56765
Remote Similarity	0.507	NPC175190
Remote Similarity	0.507	NPC506981
Remote Similarity	0.507	NPC602380
Remote Similarity	0.5051	NPC273359
Remote Similarity	0.5051	NPC56109
Remote Similarity	0.5051	NPC191382
Remote Similarity	0.5051	NPC230554
Remote Similarity	0.5051	NPC306412
Remote Similarity	0.5051	NPC203217
Remote Similarity	0.5051	NPC510017
Remote Similarity	0.5051	NPC511922

Drug Structure

NPD4075 OpenBabel08211704332D 25 28 0 0 1 0 0 0 0 0999 V2000 -3.2455 0.0699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0667 -1.3533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4238 -0.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2451 -1.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3427 -3.1551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5619 -2.7043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1233 -2.7043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -1.8032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5615 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1231 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7807 -0.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3425 -0.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7805 -1.3525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5619 -1.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7811 -1.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1234 -1.8026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7809 -0.4506 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3425 -1.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6019 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9040 -1.3518 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4236 -1.3529 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6017 -2.7757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8119 -1.5949 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 17 2 0 0 0 0 9 14 1 0 0 0 0 9 16 2 0 0 0 0 10 13 1 0 0 0 0 11 13 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 1 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 10 1 6 0 0 0 18 22 1 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC008882
DrugBank	DB04829
ChEMBL	CHEMBL263881
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	5761
ChEBI	6605
CAS Number	50-37-3

Drug Properties

Molecular Weight	323.2
ALogP	-0.0832
MLogP	3.22
XLogP	2.109
HDA	4
HBD	1
Rotatable Bonds	7
TPSA	39.34
RO5 Violation	0