NPASS drugs

Drug Information

Drug ID:	NPD1455
Drug Name:	Citicoline
Molecular Formula:	C14H26N4O11P2
Canonical SMILES:	O[C@@H]1[C@@H](COP(=O)(OP(=O)(OCC[N+](C)(C)C)O)O)O[C@H]([C@@H]1O)n1ccc(=N)nc1O
Standard InCHI:	"InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/p+1/t9-,11-,12-,13-/m1/s1"
Standard InCHIKey:	RZZPDXZPRHQOCG-OJAKKHQRSA-O
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD1455

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	110730
0.1-0.2	99990
0.2-0.3	812
0.3-0.4	157
0.4-0.5	38
0.5-0.6	5
0.6-0.7	0
0.7-0.8	7
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	0.7887	NPC328914
Intermediate Similarity	0.7879	NPC328779
Intermediate Similarity	0.7879	NPC240517
Intermediate Similarity	0.7879	NPC129
Intermediate Similarity	0.7424	NPC120887
Intermediate Similarity	0.7324	NPC126704
Intermediate Similarity	0.7031	NPC226769
Remote Similarity	0.5658	NPC329384
Remote Similarity	0.5479	NPC90240
Remote Similarity	0.5303	NPC62927
Remote Similarity	0.5119	NPC548131
Remote Similarity	0.5067	NPC329277

Drug Structure

NPD1455 OpenBabel08211700192D 37 38 0 0 1 0 0 0 0 0999 V2000 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 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 9.8025 2.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9935 1.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 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 4.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6979 3.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3198 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2709 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2709 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9754 3.0823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5070 3.8511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.7844 3.6701 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.0799 2.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 6.0108 -0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0799 -0.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0618 3.4890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 -0.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2321 -1.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2321 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3198 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 4.7321 -0.7321 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 11.4205 3.4444 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6799 -1.5032 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9754 -1.0823 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2528 2.9013 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 -3.2321 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7321 -2.4641 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 26 1 0 0 0 0 8 27 1 0 0 0 0 9 8 1 1 0 0 0 9 11 1 0 0 0 0 9 28 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 6 0 0 0 12 13 1 0 0 0 0 12 20 1 6 0 0 0 13 17 1 1 0 0 0 13 28 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 32 1 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 35 1 0 0 0 0 22 30 2 0 0 0 0 23 30 1 0 0 0 0 23 36 1 0 0 0 0 24 31 2 0 0 0 0 25 31 1 0 0 0 0 25 37 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 M CHG 1 18 1 M END $$$$

External Identifiers

TTD	DIB000426
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

Drug Properties

Molecular Weight	489.12
ALogP	-3.569
MLogP	1.13
XLogP	-3.312
HDA	14
HBD	6
Rotatable Bonds	18
TPSA	231.28
RO5 Violation	2