NPASS drugs

Drug Information

Drug ID:	NPD2204
Drug Name:
Molecular Formula:	C16H23NO6
Canonical SMILES:	O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]([C@H]1C)(C)O)(C)O
Standard InCHI:	"InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1"
Standard InCHIKey:	QVCMHGGNRFRMAD-XFGHUUIASA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD2204

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	73544
0.1-0.2	131787
0.2-0.3	6095
0.3-0.4	88
0.4-0.5	62
0.5-0.6	24
0.6-0.7	116
0.7-0.8	11
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	3

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	NPC134546
High Similarity	1.0	NPC30911
High Similarity	1.0	NPC602322
High Similarity	0.8519	NPC175904
High Similarity	0.8519	NPC608092
Intermediate Similarity	0.8364	NPC584101
Intermediate Similarity	0.7636	NPC90529
Intermediate Similarity	0.7636	NPC308013
Intermediate Similarity	0.7288	NPC550889
Intermediate Similarity	0.7241	NPC174065
Intermediate Similarity	0.7167	NPC549289
Intermediate Similarity	0.7167	NPC551635
Intermediate Similarity	0.7119	NPC133444
Intermediate Similarity	0.7119	NPC554813
Intermediate Similarity	0.7119	NPC577653
Intermediate Similarity	0.7049	NPC568438
Intermediate Similarity	0.7	NPC126619
Remote Similarity	0.6897	NPC179897
Remote Similarity	0.6897	NPC502016
Remote Similarity	0.6897	NPC509862
Remote Similarity	0.6897	NPC519326
Remote Similarity	0.6897	NPC529145
Remote Similarity	0.6897	NPC571682
Remote Similarity	0.6897	NPC593485
Remote Similarity	0.678	NPC579641
Remote Similarity	0.6774	NPC301277
Remote Similarity	0.6774	NPC316984
Remote Similarity	0.6774	NPC568801
Remote Similarity	0.6667	NPC551994
Remote Similarity	0.6667	NPC579284
Remote Similarity	0.6613	NPC563928
Remote Similarity	0.6613	NPC592098
Remote Similarity	0.6562	NPC577991
Remote Similarity	0.6557	NPC130124
Remote Similarity	0.6557	NPC323353
Remote Similarity	0.6557	NPC202434
Remote Similarity	0.6557	NPC193471
Remote Similarity	0.6557	NPC2181
Remote Similarity	0.6557	NPC172539
Remote Similarity	0.6557	NPC262172
Remote Similarity	0.6557	NPC289498
Remote Similarity	0.6557	NPC289320
Remote Similarity	0.6557	NPC172337
Remote Similarity	0.6557	NPC526703
Remote Similarity	0.6557	NPC535580
Remote Similarity	0.6557	NPC608663
Remote Similarity	0.6557	NPC589220
Remote Similarity	0.6508	NPC555407
Remote Similarity	0.6508	NPC597758
Remote Similarity	0.65	NPC508902
Remote Similarity	0.6452	NPC42494
Remote Similarity	0.6452	NPC183186
Remote Similarity	0.6452	NPC182504
Remote Similarity	0.6452	NPC39009
Remote Similarity	0.6452	NPC253549
Remote Similarity	0.6452	NPC270380
Remote Similarity	0.6452	NPC317466
Remote Similarity	0.6452	NPC15961
Remote Similarity	0.6452	NPC144015
Remote Similarity	0.6452	NPC84863
Remote Similarity	0.6452	NPC290303
Remote Similarity	0.6452	NPC507154
Remote Similarity	0.6452	NPC512634
Remote Similarity	0.6452	NPC519316
Remote Similarity	0.6452	NPC530055
Remote Similarity	0.6452	NPC532318
Remote Similarity	0.6452	NPC608751
Remote Similarity	0.6452	NPC561382
Remote Similarity	0.6452	NPC565172
Remote Similarity	0.6452	NPC581020
Remote Similarity	0.6452	NPC595869
Remote Similarity	0.6441	NPC528993
Remote Similarity	0.6393	NPC583758
Remote Similarity	0.6349	NPC329356
Remote Similarity	0.6349	NPC92562
Remote Similarity	0.6349	NPC241304
Remote Similarity	0.6349	NPC47857
Remote Similarity	0.6349	NPC245669
Remote Similarity	0.6349	NPC181510
Remote Similarity	0.6349	NPC168758
Remote Similarity	0.6349	NPC219225
Remote Similarity	0.6349	NPC37800
Remote Similarity	0.6349	NPC492981
Remote Similarity	0.6349	NPC497534
Remote Similarity	0.6349	NPC503593
Remote Similarity	0.6349	NPC503982
Remote Similarity	0.6349	NPC522537
Remote Similarity	0.6349	NPC532758
Remote Similarity	0.6349	NPC546149
Remote Similarity	0.6349	NPC609037
Remote Similarity	0.6349	NPC581740
Remote Similarity	0.6349	NPC602310
Remote Similarity	0.625	NPC147819
Remote Similarity	0.625	NPC217517
Remote Similarity	0.625	NPC79421
Remote Similarity	0.625	NPC229630
Remote Similarity	0.625	NPC207786
Remote Similarity	0.625	NPC126471
Remote Similarity	0.625	NPC23963
Remote Similarity	0.625	NPC98620
Remote Similarity	0.625	NPC205333
Remote Similarity	0.625	NPC188568
Remote Similarity	0.625	NPC318694
Remote Similarity	0.625	NPC166427
Remote Similarity	0.625	NPC16009
Remote Similarity	0.625	NPC235401
Remote Similarity	0.625	NPC201889
Remote Similarity	0.625	NPC168465
Remote Similarity	0.625	NPC106791
Remote Similarity	0.625	NPC160309
Remote Similarity	0.625	NPC607716
Remote Similarity	0.625	NPC540908
Remote Similarity	0.625	NPC554795
Remote Similarity	0.625	NPC608959
Remote Similarity	0.625	NPC563868
Remote Similarity	0.625	NPC578631
Remote Similarity	0.619	NPC536975
Remote Similarity	0.6154	NPC113763
Remote Similarity	0.6154	NPC497488
Remote Similarity	0.6154	NPC512648
Remote Similarity	0.6154	NPC531105
Remote Similarity	0.6154	NPC553060
Remote Similarity	0.6154	NPC559659
Remote Similarity	0.6066	NPC181492
Remote Similarity	0.6066	NPC501492
Remote Similarity	0.6066	NPC524691
Remote Similarity	0.6066	NPC554053
Remote Similarity	0.6066	NPC562578
Remote Similarity	0.6061	NPC509682
Remote Similarity	0.6061	NPC540530
Remote Similarity	0.6034	NPC503470
Remote Similarity	0.6	NPC9535
Remote Similarity	0.6	NPC492997
Remote Similarity	0.5873	NPC166680
Remote Similarity	0.5873	NPC551597
Remote Similarity	0.5821	NPC219124
Remote Similarity	0.5821	NPC12075
Remote Similarity	0.5821	NPC490887
Remote Similarity	0.5821	NPC566536
Remote Similarity	0.5806	NPC527291
Remote Similarity	0.5797	NPC545042
Remote Similarity	0.5606	NPC318242
Remote Similarity	0.5606	NPC96328
Remote Similarity	0.5606	NPC582729
Remote Similarity	0.5424	NPC578947
Remote Similarity	0.5417	NPC37110
Remote Similarity	0.5417	NPC132976
Remote Similarity	0.5303	NPC610562
Remote Similarity	0.5303	NPC580305
Remote Similarity	0.5286	NPC529437
Remote Similarity	0.5286	NPC600980
Remote Similarity	0.5286	NPC581531
Remote Similarity	0.5224	NPC544185
Remote Similarity	0.5147	NPC226376
Remote Similarity	0.5147	NPC54493
Remote Similarity	0.5147	NPC493782
Remote Similarity	0.5082	NPC516730

Drug Structure

NPD2204 OpenBabel08211701392D 25 27 0 0 1 0 0 0 0 0999 V2000 0.7226 2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 1.1698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 -0.2702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1442 -2.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7507 0.1091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1824 -2.5642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1753 -0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9928 -1.7196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9928 0.9928 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7196 -1.7196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7125 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4954 -1.0211 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7196 0.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3634 0.6294 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3995 -1.5431 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.9898 2.0012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 -0.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0932 1.6378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7382 0.7382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3634 -1.3562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3491 0.6294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9151 1.9080 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7465 0.4680 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 15 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 1 0 0 0 0 6 17 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 1 0 0 0 10 12 1 0 0 0 0 11 5 1 6 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 17 1 6 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 6 0 0 0 15 20 1 0 0 0 0 16 3 1 1 0 0 0 16 21 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNAP001636
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	9415
ChEBI
CAS Number

Drug Properties

Molecular Weight	325.15
ALogP	-0.5674
MLogP	2.45
XLogP	0.018
HDA	7
HBD	2
Rotatable Bonds	5
TPSA	96.3
RO5 Violation	0