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 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	55
0.1-0.2	8389
0.2-0.3	18923
0.3-0.4	2899
0.4-0.5	512
0.5-0.6	69
0.6-0.7	15
0.7-0.8	16
0.8-0.85	2
0.85-0.9	2
0.9-0.95	2
0.95-1	6

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	NPC328914
High Similarity	0.978	NPC328779
High Similarity	0.967	NPC120887
High Similarity	0.956	NPC280946
High Similarity	0.956	NPC6166
High Similarity	0.956	NPC226769
High Similarity	0.9451	NPC329384
High Similarity	0.9247	NPC90240
High Similarity	0.8791	NPC62927
High Similarity	0.8791	NPC190334
Intermediate Similarity	0.8462	NPC229249
Intermediate Similarity	0.8105	NPC328806
Intermediate Similarity	0.798	NPC73765
Intermediate Similarity	0.798	NPC283698
Intermediate Similarity	0.7879	NPC36985
Intermediate Similarity	0.7879	NPC17892
Intermediate Similarity	0.7677	NPC320249
Intermediate Similarity	0.7677	NPC322594
Intermediate Similarity	0.7576	NPC324390
Intermediate Similarity	0.757	NPC329277
Intermediate Similarity	0.7317	NPC318142
Intermediate Similarity	0.7282	NPC317639
Intermediate Similarity	0.7273	NPC155087
Intermediate Similarity	0.7273	NPC149843
Intermediate Similarity	0.7184	NPC324516
Intermediate Similarity	0.7184	NPC318166
Intermediate Similarity	0.7172	NPC43246
Intermediate Similarity	0.7172	NPC89051
Remote Similarity	0.699	NPC327344
Remote Similarity	0.6989	NPC315806
Remote Similarity	0.6983	NPC313813
Remote Similarity	0.6961	NPC315063
Remote Similarity	0.6869	NPC106780
Remote Similarity	0.6733	NPC325723
Remote Similarity	0.6602	NPC163352
Remote Similarity	0.6602	NPC210456
Remote Similarity	0.64	NPC284651
Remote Similarity	0.6311	NPC71339
Remote Similarity	0.6311	NPC112842
Remote Similarity	0.6263	NPC329077
Remote Similarity	0.6168	NPC171116
Remote Similarity	0.6162	NPC469972
Remote Similarity	0.604	NPC325902
Remote Similarity	0.5969	NPC315058
Remote Similarity	0.5906	NPC245534
Remote Similarity	0.5887	NPC64705
Remote Similarity	0.5887	NPC232408
Remote Similarity	0.5847	NPC62845
Remote Similarity	0.5847	NPC166242
Remote Similarity	0.5847	NPC189854
Remote Similarity	0.5847	NPC322449
Remote Similarity	0.5847	NPC92874
Remote Similarity	0.5833	NPC313962
Remote Similarity	0.5816	NPC317746
Remote Similarity	0.5816	NPC177169
Remote Similarity	0.5798	NPC325900
Remote Similarity	0.5798	NPC10897
Remote Similarity	0.5763	NPC314398
Remote Similarity	0.5763	NPC314413
Remote Similarity	0.5763	NPC239705
Remote Similarity	0.5745	NPC251233
Remote Similarity	0.5745	NPC318590
Remote Similarity	0.5745	NPC211820
Remote Similarity	0.5603	NPC186619

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
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