NPASS drugs

Drug Information

Drug ID:	NPD802
Drug Name:	Psilocybine
Molecular Formula:	C12H17N2O4P
Canonical SMILES:	CN(CCc1c[nH]c2c1c(ccc2)OP(=O)(O)O)C
Standard InCHI:	"InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)"
Standard InCHIKey:	QVDSEJDULKLHCG-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD802

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	139015
0.1-0.2	69235
0.2-0.3	3153
0.3-0.4	311
0.4-0.5	11
0.5-0.6	8
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
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	NPC106937
High Similarity	1.0	NPC599808
Remote Similarity	0.6545	NPC549201
Remote Similarity	0.6545	NPC610692
Remote Similarity	0.6429	NPC560252
Remote Similarity	0.5577	NPC577450
Remote Similarity	0.5273	NPC13880
Remote Similarity	0.5185	NPC73767
Remote Similarity	0.5185	NPC599801
Remote Similarity	0.5172	NPC92111
Remote Similarity	0.5172	NPC611386
Remote Similarity	0.5088	NPC507754
Remote Similarity	0.5088	NPC600620

Drug Structure

NPD802 OpenBabel08201723412D 22 23 0 0 0 0 0 0 0 0999 V2000 -2.2076 0.0674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3666 -1.2197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7213 -1.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -1.5798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0827 -2.9345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0219 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8309 -3.3412 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4155 -0.9107 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 -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 0.0000 0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 1.0388 -4.3194 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 H 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 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 13 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 18 19 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

Drug Properties

Molecular Weight	284.09
ALogP	-0.3315
MLogP	2.01
XLogP	-0.053
HDA	5
HBD	3
Rotatable Bonds	9
TPSA	95.6
RO5 Violation	0