NPASS drugs

Drug Information

Drug ID:	NPD2972
Drug Name:	Codeine
Molecular Formula:	C18H21NO3
Canonical SMILES:	COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C
Standard InCHI:	"InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1"
Standard InCHIKey:	OROGSEYTTFOCAN-DNJOTXNNSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2972

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	55972
0.1-0.2	151211
0.2-0.3	4370
0.3-0.4	119
0.4-0.5	24
0.5-0.6	11
0.6-0.7	21
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	7

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	NPC43069
High Similarity	1.0	NPC235802
High Similarity	1.0	NPC262786
High Similarity	1.0	NPC163601
High Similarity	1.0	NPC2073
High Similarity	1.0	NPC319632
High Similarity	1.0	NPC612004
High Similarity	0.875	NPC140577
High Similarity	0.875	NPC146628
Intermediate Similarity	0.8	NPC44953
Remote Similarity	0.6914	NPC26746
Remote Similarity	0.6857	NPC328423
Remote Similarity	0.6857	NPC74436
Remote Similarity	0.6857	NPC232533
Remote Similarity	0.6857	NPC298343
Remote Similarity	0.6857	NPC566104
Remote Similarity	0.6857	NPC607466
Remote Similarity	0.6857	NPC608460
Remote Similarity	0.6812	NPC318674
Remote Similarity	0.6812	NPC305440
Remote Similarity	0.6812	NPC214629
Remote Similarity	0.6812	NPC67346
Remote Similarity	0.6812	NPC174783
Remote Similarity	0.6812	NPC599847
Remote Similarity	0.6761	NPC485664
Remote Similarity	0.6625	NPC143927
Remote Similarity	0.6389	NPC23347
Remote Similarity	0.6389	NPC203778
Remote Similarity	0.6389	NPC322178
Remote Similarity	0.6027	NPC160593
Remote Similarity	0.6027	NPC581397
Remote Similarity	0.5789	NPC580459
Remote Similarity	0.5753	NPC115906
Remote Similarity	0.5753	NPC608430
Remote Similarity	0.5733	NPC550752
Remote Similarity	0.5714	NPC311781
Remote Similarity	0.5714	NPC238919
Remote Similarity	0.5714	NPC70075
Remote Similarity	0.5682	NPC320999
Remote Similarity	0.56	NPC327766
Remote Similarity	0.56	NPC33179
Remote Similarity	0.5513	NPC243483

Drug Structure

NPD2972 OpenBabel08211702562D 23 27 0 0 1 0 0 0 0 0999 V2000 -4.0830 -1.6204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3650 2.8821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 1.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 -1.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4411 -2.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4411 2.1107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6350 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9037 0.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 0.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 -0.8445 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9037 -0.4222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7098 -1.6889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7098 1.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4411 0.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7098 0.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7098 -0.8445 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4411 -0.4222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6350 -0.8445 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0215 -2.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0215 2.1107 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 0.7177 -1.6332 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 21 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 9 1 6 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 1 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 1 0 0 0 17 22 1 0 0 0 0 18 7 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000213
DrugBank	DB00318
ChEMBL	CHEMBL485
IUPHAR/BPS	1673
PharmaGKB	PA449088
KEGG Drug	D03580
PubChem CID	5284371
ChEBI	16714
CAS Number	76-57-3

Drug Properties

Molecular Weight	299.15
ALogP	-0.19
MLogP	3
XLogP	0.433
HDA	4
HBD	1
Rotatable Bonds	4
TPSA	41.93
RO5 Violation	0