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

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
Intermediate Similarity	0.8415	NPC260814
Intermediate Similarity	0.8415	NPC323249
Intermediate Similarity	0.8372	NPC125290
Intermediate Similarity	0.8125	NPC67076
Intermediate Similarity	0.8125	NPC319163
Intermediate Similarity	0.8118	NPC316844
Intermediate Similarity	0.8	NPC477215
Intermediate Similarity	0.8	NPC476388
Intermediate Similarity	0.7957	NPC476487
Intermediate Similarity	0.7957	NPC476488
Intermediate Similarity	0.7955	NPC261380
Intermediate Similarity	0.7931	NPC477786
Intermediate Similarity	0.7931	NPC477785
Intermediate Similarity	0.7931	NPC477784
Intermediate Similarity	0.7931	NPC62214
Intermediate Similarity	0.7912	NPC145666
Intermediate Similarity	0.7895	NPC235464
Intermediate Similarity	0.7895	NPC166745
Intermediate Similarity	0.7895	NPC197386
Intermediate Similarity	0.7889	NPC476805
Intermediate Similarity	0.7882	NPC476624
Intermediate Similarity	0.7882	NPC472013
Intermediate Similarity	0.7865	NPC261721
Intermediate Similarity	0.7865	NPC315395
Intermediate Similarity	0.7865	NPC316426
Intermediate Similarity	0.7835	NPC118405
Intermediate Similarity	0.7826	NPC261607
Intermediate Similarity	0.7826	NPC111114
Intermediate Similarity	0.7826	NPC300312
Intermediate Similarity	0.7816	NPC85772
Intermediate Similarity	0.7805	NPC275098
Intermediate Similarity	0.7802	NPC310236
Intermediate Similarity	0.7802	NPC170775
Intermediate Similarity	0.7778	NPC318766
Intermediate Similarity	0.7778	NPC72513
Intermediate Similarity	0.7778	NPC237540
Intermediate Similarity	0.7766	NPC54905
Intermediate Similarity	0.7766	NPC314009
Intermediate Similarity	0.7765	NPC93763
Intermediate Similarity	0.7765	NPC108816
Intermediate Similarity	0.7765	NPC476627
Intermediate Similarity	0.7765	NPC231739
Intermediate Similarity	0.7753	NPC28887
Intermediate Similarity	0.7753	NPC470755
Intermediate Similarity	0.775	NPC476614
Intermediate Similarity	0.7742	NPC469645
Intermediate Similarity	0.7742	NPC469692
Intermediate Similarity	0.7738	NPC469646
Intermediate Similarity	0.7732	NPC282524
Intermediate Similarity	0.7727	NPC16488
Intermediate Similarity	0.7717	NPC106510
Intermediate Similarity	0.7717	NPC71533
Intermediate Similarity	0.7711	NPC227396
Intermediate Similarity	0.7708	NPC141191
Intermediate Similarity	0.7701	NPC325031
Intermediate Similarity	0.7701	NPC471325
Intermediate Similarity	0.77	NPC91034
Intermediate Similarity	0.7692	NPC476803
Intermediate Similarity	0.7692	NPC249889
Intermediate Similarity	0.7692	NPC193843
Intermediate Similarity	0.7684	NPC29152
Intermediate Similarity	0.7684	NPC250757
Intermediate Similarity	0.7684	NPC301534
Intermediate Similarity	0.7677	NPC309190
Intermediate Similarity	0.7674	NPC226226
Intermediate Similarity	0.7674	NPC55304
Intermediate Similarity	0.7674	NPC113363
Intermediate Similarity	0.7667	NPC469483
Intermediate Similarity	0.7667	NPC305475
Intermediate Similarity	0.7667	NPC475461
Intermediate Similarity	0.766	NPC53685
Intermediate Similarity	0.766	NPC65829
Intermediate Similarity	0.766	NPC121825
Intermediate Similarity	0.766	NPC167219
Intermediate Similarity	0.7654	NPC143396
Intermediate Similarity	0.7653	NPC204450
Intermediate Similarity	0.7653	NPC195290
Intermediate Similarity	0.7647	NPC320630
Intermediate Similarity	0.7647	NPC116177
Intermediate Similarity	0.7647	NPC472014
Intermediate Similarity	0.7647	NPC276769
Intermediate Similarity	0.7647	NPC281296
Intermediate Similarity	0.7647	NPC7563
Intermediate Similarity	0.7647	NPC471061
Intermediate Similarity	0.764	NPC476804
Intermediate Similarity	0.764	NPC158756
Intermediate Similarity	0.764	NPC141193
Intermediate Similarity	0.764	NPC96259
Intermediate Similarity	0.7619	NPC251435
Intermediate Similarity	0.7609	NPC268298
Intermediate Similarity	0.7609	NPC214387
Intermediate Similarity	0.7609	NPC232747
Intermediate Similarity	0.7604	NPC107243
Intermediate Similarity	0.7604	NPC156546
Intermediate Similarity	0.7604	NPC87090
Intermediate Similarity	0.7604	NPC169205
Intermediate Similarity	0.7604	NPC477949
Intermediate Similarity	0.7586	NPC45495
Intermediate Similarity	0.7582	NPC471738
Intermediate Similarity	0.7582	NPC316629
Intermediate Similarity	0.7579	NPC476174
Intermediate Similarity	0.7576	NPC475050
Intermediate Similarity	0.7576	NPC236390
Intermediate Similarity	0.7558	NPC267231
Intermediate Similarity	0.7558	NPC218817
Intermediate Similarity	0.7558	NPC172066
Intermediate Similarity	0.7558	NPC478122
Intermediate Similarity	0.7558	NPC11796
Intermediate Similarity	0.7558	NPC121200
Intermediate Similarity	0.7558	NPC128276
Intermediate Similarity	0.7558	NPC475994
Intermediate Similarity	0.7556	NPC255307
Intermediate Similarity	0.7556	NPC165162
Intermediate Similarity	0.7556	NPC179006
Intermediate Similarity	0.7556	NPC474853
Intermediate Similarity	0.7556	NPC476628
Intermediate Similarity	0.7553	NPC125180
Intermediate Similarity	0.7551	NPC99411
Intermediate Similarity	0.7551	NPC476240
Intermediate Similarity	0.7551	NPC472924
Intermediate Similarity	0.7551	NPC224720
Intermediate Similarity	0.7551	NPC476223
Intermediate Similarity	0.7551	NPC477950
Intermediate Similarity	0.7551	NPC171759
Intermediate Similarity	0.7551	NPC150923
Intermediate Similarity	0.7549	NPC475941
Intermediate Similarity	0.7549	NPC47951
Intermediate Similarity	0.7549	NPC474901
Intermediate Similarity	0.7528	NPC52609
Intermediate Similarity	0.7528	NPC169575
Intermediate Similarity	0.7528	NPC40746
Intermediate Similarity	0.7528	NPC1761
Intermediate Similarity	0.7527	NPC477149
Intermediate Similarity	0.7527	NPC473448
Intermediate Similarity	0.7527	NPC129419
Intermediate Similarity	0.7527	NPC477147
Intermediate Similarity	0.7527	NPC77337
Intermediate Similarity	0.75	NPC456
Intermediate Similarity	0.75	NPC191620
Intermediate Similarity	0.75	NPC475970
Intermediate Similarity	0.75	NPC185553
Intermediate Similarity	0.75	NPC191711
Intermediate Similarity	0.75	NPC470241
Intermediate Similarity	0.75	NPC472941
Intermediate Similarity	0.75	NPC475819
Intermediate Similarity	0.7475	NPC87351
Intermediate Similarity	0.7474	NPC90453
Intermediate Similarity	0.7473	NPC194417
Intermediate Similarity	0.7473	NPC469910
Intermediate Similarity	0.7471	NPC178277
Intermediate Similarity	0.7471	NPC7232
Intermediate Similarity	0.747	NPC29328
Intermediate Similarity	0.7451	NPC220155
Intermediate Similarity	0.7449	NPC476274
Intermediate Similarity	0.7449	NPC266955
Intermediate Similarity	0.7449	NPC287833
Intermediate Similarity	0.7447	NPC45269
Intermediate Similarity	0.7447	NPC473986
Intermediate Similarity	0.7447	NPC475925
Intermediate Similarity	0.7447	NPC474018
Intermediate Similarity	0.7447	NPC221282
Intermediate Similarity	0.7447	NPC476705
Intermediate Similarity	0.7444	NPC472957
Intermediate Similarity	0.7444	NPC7927
Intermediate Similarity	0.7444	NPC165287
Intermediate Similarity	0.7444	NPC472958
Intermediate Similarity	0.7444	NPC114979
Intermediate Similarity	0.7444	NPC472326
Intermediate Similarity	0.7444	NPC230527
Intermediate Similarity	0.7444	NPC191476
Intermediate Similarity	0.7442	NPC57744
Intermediate Similarity	0.7439	NPC67608
Intermediate Similarity	0.7423	NPC53844
Intermediate Similarity	0.7423	NPC108475
Intermediate Similarity	0.7423	NPC161493
Intermediate Similarity	0.7423	NPC253826
Intermediate Similarity	0.7423	NPC475894
Intermediate Similarity	0.7423	NPC213947
Intermediate Similarity	0.7423	NPC170143
Intermediate Similarity	0.7423	NPC57416
Intermediate Similarity	0.7419	NPC117405
Intermediate Similarity	0.7419	NPC307092
Intermediate Similarity	0.7419	NPC123912
Intermediate Similarity	0.7419	NPC155479
Intermediate Similarity	0.7419	NPC212598
Intermediate Similarity	0.7419	NPC295312
Intermediate Similarity	0.7419	NPC51358
Intermediate Similarity	0.7419	NPC52198
Intermediate Similarity	0.7416	NPC256750
Intermediate Similarity	0.7416	NPC133844

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