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:	Approved
Max Developmental Stage Source:	TTD; DrugBank

Structural Similarity Between NPASS Natural Products and NPD5363

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	110
0.1-0.2	683
0.2-0.3	3246
0.3-0.4	7966
0.4-0.5	9140
0.5-0.6	5002
0.6-0.7	3951
0.7-0.8	774
0.8-0.85	10
0.85-0.9	3
0.9-0.95	4
0.95-1	1

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

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Similarity Level	Similarity Score	Natural Product ID
High Similarity	0.962	NPC7414
High Similarity	0.9494	NPC47031
High Similarity	0.9367	NPC115418
High Similarity	0.9241	NPC164308
High Similarity	0.9241	NPC201225
High Similarity	0.8875	NPC192006
High Similarity	0.8861	NPC279537
High Similarity	0.878	NPC88735
Intermediate Similarity	0.8415	NPC27949
Intermediate Similarity	0.8415	NPC39547

Showing 1 to 10 of 200 entries

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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