NPASS drugs

Drug Information

Drug ID:	NPD5363
Drug Name:	Limaprost
Molecular Formula:	C22H36O5
Canonical SMILES:	CCCC[C@@H](C[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCC/C=C/C(=O)O)O)C
Standard InCHI:	"InChI=1S/C22H36O5/c1-3-4-9-16(2)14-17(23)12-13-19-18(20(24)15-21(19)25)10-7-5-6-8-11-22(26)27/h8,11-13,16-19,21,23,25H,3-7,9-10,14-15H2,1-2H3,(H,26,27)/b11-8+,13-12+/t16-,17+,18+,19+,21+/m0/s1"
Standard InCHIKey:	OJZYRQPMEIEQFC-UAWLTFRCSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	TTD; DrugBank

Structural Similarity Between NPASS Natural Products and NPD5363

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	71288
0.1-0.2	132475
0.2-0.3	7732
0.3-0.4	218
0.4-0.5	23
0.5-0.6	1
0.6-0.7	3
0.7-0.8	0
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
Remote Similarity	0.623	NPC7414
Remote Similarity	0.623	NPC292220
Remote Similarity	0.623	NPC599781
Remote Similarity	0.5556	NPC12355

Drug Structure

NPD5363 OpenBabel08211706322D 30 30 0 0 1 0 0 0 0 0999 V2000 -5.7189 -2.7547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 -1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7679 -3.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0247 -2.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2327 -1.4164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 0.2308 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 -3.4895 -0.7473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9543 0.9000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 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 5.6962 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1622 1.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4190 2.5472 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 1.0388 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 16 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 2 1 1 0 0 0 17 12 1 6 0 0 0 17 23 1 0 0 0 0 18 10 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 13 1 6 0 0 0 19 21 1 0 0 0 0 20 24 2 0 0 0 0 21 25 1 1 0 0 0 22 26 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 25 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNAP001487
DrugBank	DB09211
ChEMBL	CHEMBL2107456
IUPHAR/BPS
PharmaGKB
KEGG Drug	D02722
PubChem CID	6438378
ChEBI	135594
CAS Number	74397-12-9

Drug Properties

Molecular Weight	380.26
ALogP	-1.057
MLogP	3.33
XLogP	4.272
HDA	5
HBD	3
Rotatable Bonds	18
TPSA	94.83
RO5 Violation	1