NPASS drugs

Drug Information

Drug ID:	NPD4191
Drug Name:	Tretinoin
Molecular Formula:	C20H28O2
Canonical SMILES:	CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
Standard InCHI:	"InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)"
Standard InCHIKey:	SHGAZHPCJJPHSC-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD4191

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	133693
0.1-0.2	73669
0.2-0.3	3798
0.3-0.4	390
0.4-0.5	83
0.5-0.6	55
0.6-0.7	33
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	8

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	NPC329416
High Similarity	1.0	NPC317025
High Similarity	1.0	NPC326645
High Similarity	1.0	NPC317177
High Similarity	1.0	NPC607228
High Similarity	1.0	NPC608474
High Similarity	1.0	NPC611716
High Similarity	1.0	NPC611761
Intermediate Similarity	0.75	NPC512116
Remote Similarity	0.6977	NPC317176
Remote Similarity	0.6744	NPC242504
Remote Similarity	0.6744	NPC529696
Remote Similarity	0.6739	NPC254886
Remote Similarity	0.6739	NPC512807
Remote Similarity	0.6739	NPC516698
Remote Similarity	0.6739	NPC584261
Remote Similarity	0.6596	NPC176632
Remote Similarity	0.6596	NPC504600
Remote Similarity	0.6591	NPC324869
Remote Similarity	0.6591	NPC537691
Remote Similarity	0.6458	NPC323433
Remote Similarity	0.6429	NPC22019
Remote Similarity	0.6429	NPC281986
Remote Similarity	0.6429	NPC328240
Remote Similarity	0.6429	NPC608491
Remote Similarity	0.641	NPC17810
Remote Similarity	0.641	NPC104168
Remote Similarity	0.641	NPC45489
Remote Similarity	0.641	NPC205394
Remote Similarity	0.641	NPC519835
Remote Similarity	0.641	NPC606095
Remote Similarity	0.641	NPC611666
Remote Similarity	0.6316	NPC327445
Remote Similarity	0.6316	NPC497002
Remote Similarity	0.6279	NPC493679
Remote Similarity	0.625	NPC67149
Remote Similarity	0.625	NPC505989
Remote Similarity	0.6136	NPC113289
Remote Similarity	0.6136	NPC495737
Remote Similarity	0.6136	NPC550993
Remote Similarity	0.6136	NPC553630
Remote Similarity	0.6078	NPC583375
Remote Similarity	0.5909	NPC582361
Remote Similarity	0.5814	NPC540572
Remote Similarity	0.5778	NPC106603
Remote Similarity	0.5778	NPC248404
Remote Similarity	0.5778	NPC531201
Remote Similarity	0.5778	NPC544207
Remote Similarity	0.5778	NPC547497
Remote Similarity	0.5778	NPC573796
Remote Similarity	0.5778	NPC578984
Remote Similarity	0.5652	NPC567686
Remote Similarity	0.5556	NPC55412
Remote Similarity	0.5556	NPC249645
Remote Similarity	0.5556	NPC250034
Remote Similarity	0.5556	NPC319251
Remote Similarity	0.5556	NPC506962
Remote Similarity	0.5556	NPC570331
Remote Similarity	0.5556	NPC611871
Remote Similarity	0.5536	NPC513559
Remote Similarity	0.5532	NPC204433
Remote Similarity	0.5532	NPC494143
Remote Similarity	0.5526	NPC594314
Remote Similarity	0.5435	NPC531568
Remote Similarity	0.5435	NPC578375
Remote Similarity	0.5435	NPC582373
Remote Similarity	0.54	NPC598418
Remote Similarity	0.5319	NPC549756
Remote Similarity	0.5319	NPC559834
Remote Similarity	0.5319	NPC573989
Remote Similarity	0.5306	NPC44155
Remote Similarity	0.5306	NPC191407
Remote Similarity	0.5306	NPC507044
Remote Similarity	0.5306	NPC528116
Remote Similarity	0.5306	NPC529987
Remote Similarity	0.5306	NPC563107
Remote Similarity	0.5306	NPC563781
Remote Similarity	0.5208	NPC268613
Remote Similarity	0.5208	NPC267296
Remote Similarity	0.5208	NPC497575
Remote Similarity	0.5208	NPC500057
Remote Similarity	0.5208	NPC509058
Remote Similarity	0.5208	NPC590325
Remote Similarity	0.52	NPC226066
Remote Similarity	0.52	NPC499012
Remote Similarity	0.52	NPC564400
Remote Similarity	0.52	NPC573148
Remote Similarity	0.52	NPC611615
Remote Similarity	0.5102	NPC278430
Remote Similarity	0.5102	NPC164487
Remote Similarity	0.5102	NPC2660
Remote Similarity	0.5102	NPC117733
Remote Similarity	0.5102	NPC55681
Remote Similarity	0.5102	NPC510171
Remote Similarity	0.5102	NPC517816
Remote Similarity	0.5098	NPC284192
Remote Similarity	0.5098	NPC529782

Drug Structure

NPD4191 OpenBabel08211704332D 23 23 0 0 0 0 0 0 0 0999 V2000 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 9 2 3 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 15 2 3 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 3 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 3 0 0 0 14 19 1 0 0 0 0 17 18 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 22 2 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC000117
DrugBank	DB00755
ChEMBL	CHEMBL38
IUPHAR/BPS
PharmaGKB	PA451746
KEGG Drug	D00094
PubChem CID	0
ChEBI	15367
CAS Number	302-79-4

Drug Properties

Molecular Weight	300.21
ALogP	3.8871
MLogP	3.44
XLogP	6.254
HDA	2
HBD	1
Rotatable Bonds	11
TPSA	37.3
RO5 Violation	1