NPASS drugs

Drug Information

Drug ID:	NPD5331
Drug Name:	iloprost
Molecular Formula:	C22H32O4
Canonical SMILES:	CC#CCC([C@@H](/C=C/C1[C@H](O)C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)C
Standard InCHI:	InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18?,19-,20+,21+/m0/s1
Standard InCHIKey:	HIFJCPQKFCZDDL-SGSAMSKHSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5331

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	103
0.1-0.2	635
0.2-0.3	3585
0.3-0.4	11304
0.4-0.5	6451
0.5-0.6	5541
0.6-0.7	3095
0.7-0.8	165
0.8-0.85	5
0.85-0.9	6
0.9-0.95	0
0.95-1	0

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	0.8625	NPC323249
High Similarity	0.8625	NPC39547
High Similarity	0.8625	NPC260814
High Similarity	0.8625	NPC27949
High Similarity	0.8537	NPC88735
High Similarity	0.8537	NPC316844
Intermediate Similarity	0.8434	NPC7414
Intermediate Similarity	0.8375	NPC279537
Intermediate Similarity	0.8313	NPC47031
Intermediate Similarity	0.8293	NPC201225
Intermediate Similarity	0.8193	NPC115418
Intermediate Similarity	0.7955	NPC316629
Intermediate Similarity	0.7949	NPC224532
Intermediate Similarity	0.7907	NPC472473
Intermediate Similarity	0.7889	NPC472466
Intermediate Similarity	0.7882	NPC472471
Intermediate Similarity	0.7802	NPC472468
Intermediate Similarity	0.7778	NPC477215
Intermediate Similarity	0.7778	NPC476388
Intermediate Similarity	0.7742	NPC472469
Intermediate Similarity	0.7738	NPC192006
Intermediate Similarity	0.7711	NPC310643
Intermediate Similarity	0.7634	NPC472467
Intermediate Similarity	0.7619	NPC476439
Intermediate Similarity	0.7586	NPC472465
Intermediate Similarity	0.7582	NPC232747
Intermediate Similarity	0.7558	NPC472470
Intermediate Similarity	0.7531	NPC4299
Intermediate Similarity	0.75	NPC477667
Intermediate Similarity	0.75	NPC472472
Intermediate Similarity	0.7447	NPC90453
Intermediate Similarity	0.7444	NPC477668
Intermediate Similarity	0.7442	NPC164308
Intermediate Similarity	0.7439	NPC319163
Intermediate Similarity	0.7439	NPC67076
Intermediate Similarity	0.7419	NPC45269
Intermediate Similarity	0.7416	NPC165064
Intermediate Similarity	0.7407	NPC101622
Intermediate Similarity	0.7396	NPC107243
Intermediate Similarity	0.7396	NPC475894
Intermediate Similarity	0.7391	NPC155479
Intermediate Similarity	0.7391	NPC310236
Intermediate Similarity	0.7381	NPC113639
Intermediate Similarity	0.7363	NPC312215
Intermediate Similarity	0.7363	NPC128644
Intermediate Similarity	0.7349	NPC14352
Intermediate Similarity	0.7349	NPC234527
Intermediate Similarity	0.7333	NPC269638
Intermediate Similarity	0.7326	NPC172066
Intermediate Similarity	0.732	NPC166745
Intermediate Similarity	0.732	NPC235464
Intermediate Similarity	0.732	NPC197386
Intermediate Similarity	0.7317	NPC318766
Intermediate Similarity	0.7312	NPC46281
Intermediate Similarity	0.7283	NPC247406
Intermediate Similarity	0.7283	NPC249889
Intermediate Similarity	0.7283	NPC48866
Intermediate Similarity	0.7283	NPC294480
Intermediate Similarity	0.7283	NPC193843
Intermediate Similarity	0.7273	NPC191711
Intermediate Similarity	0.7263	NPC7165
Intermediate Similarity	0.7253	NPC212843
Intermediate Similarity	0.7241	NPC55304
Intermediate Similarity	0.7241	NPC226226
Intermediate Similarity	0.7229	NPC472254
Intermediate Similarity	0.7216	NPC161493
Intermediate Similarity	0.7216	NPC57416
Intermediate Similarity	0.7216	NPC469432
Intermediate Similarity	0.7215	NPC470320
Intermediate Similarity	0.7215	NPC226592
Intermediate Similarity	0.7209	NPC276769
Intermediate Similarity	0.7204	NPC2983
Intermediate Similarity	0.7204	NPC214387
Intermediate Similarity	0.7195	NPC22301
Intermediate Similarity	0.7188	NPC476487
Intermediate Similarity	0.7188	NPC54905
Intermediate Similarity	0.7188	NPC476488
Intermediate Similarity	0.7188	NPC314009
Intermediate Similarity	0.7188	NPC67584
Intermediate Similarity	0.7188	NPC52044
Intermediate Similarity	0.7179	NPC475984
Intermediate Similarity	0.7176	NPC199445
Intermediate Similarity	0.7176	NPC313185
Intermediate Similarity	0.7174	NPC237540
Intermediate Similarity	0.716	NPC477791
Intermediate Similarity	0.716	NPC99619
Intermediate Similarity	0.716	NPC26500
Intermediate Similarity	0.7159	NPC200446
Intermediate Similarity	0.7158	NPC243866
Intermediate Similarity	0.7158	NPC472942
Intermediate Similarity	0.7143	NPC122239
Intermediate Similarity	0.7143	NPC477085
Intermediate Similarity	0.7143	NPC48647
Intermediate Similarity	0.7128	NPC37607
Intermediate Similarity	0.7128	NPC477149
Intermediate Similarity	0.7128	NPC320026
Intermediate Similarity	0.7128	NPC123854
Intermediate Similarity	0.7128	NPC477147
Intermediate Similarity	0.7128	NPC69622
Intermediate Similarity	0.7128	NPC301969
Intermediate Similarity	0.7126	NPC121200
Intermediate Similarity	0.7125	NPC477009
Intermediate Similarity	0.7125	NPC238352
Intermediate Similarity	0.7113	NPC155676
Intermediate Similarity	0.7113	NPC213078
Intermediate Similarity	0.71	NPC195290
Intermediate Similarity	0.71	NPC204450
Intermediate Similarity	0.71	NPC118405
Intermediate Similarity	0.7097	NPC183546
Intermediate Similarity	0.7093	NPC12740
Intermediate Similarity	0.7093	NPC110461
Intermediate Similarity	0.7093	NPC470899
Intermediate Similarity	0.7093	NPC61863
Intermediate Similarity	0.7093	NPC469646
Intermediate Similarity	0.7089	NPC470965
Intermediate Similarity	0.7089	NPC29697
Intermediate Similarity	0.7083	NPC469406
Intermediate Similarity	0.7079	NPC59994
Intermediate Similarity	0.7079	NPC52861
Intermediate Similarity	0.7079	NPC470241
Intermediate Similarity	0.7079	NPC325031
Intermediate Similarity	0.7079	NPC112868
Intermediate Similarity	0.7079	NPC78677
Intermediate Similarity	0.7065	NPC80590
Intermediate Similarity	0.7065	NPC469994
Intermediate Similarity	0.7065	NPC116575
Intermediate Similarity	0.7065	NPC155011
Intermediate Similarity	0.7059	NPC309178
Intermediate Similarity	0.7059	NPC227396
Intermediate Similarity	0.7059	NPC471659
Intermediate Similarity	0.7053	NPC154101
Intermediate Similarity	0.7053	NPC475925
Intermediate Similarity	0.7045	NPC89128
Intermediate Similarity	0.7045	NPC209995
Intermediate Similarity	0.7041	NPC477949
Intermediate Similarity	0.7041	NPC475438
Intermediate Similarity	0.7033	NPC475732
Intermediate Similarity	0.7033	NPC194937
Intermediate Similarity	0.7033	NPC295799
Intermediate Similarity	0.7033	NPC476804
Intermediate Similarity	0.7033	NPC474776
Intermediate Similarity	0.7033	NPC476038
Intermediate Similarity	0.703	NPC236390
Intermediate Similarity	0.7024	NPC477087
Intermediate Similarity	0.7024	NPC471662
Intermediate Similarity	0.7024	NPC477983
Intermediate Similarity	0.7024	NPC477981
Intermediate Similarity	0.7024	NPC477086
Intermediate Similarity	0.7021	NPC146554
Intermediate Similarity	0.7021	NPC170775
Intermediate Similarity	0.7021	NPC54689
Intermediate Similarity	0.7021	NPC128496
Intermediate Similarity	0.7013	NPC329819
Intermediate Similarity	0.7011	NPC40049
Intermediate Similarity	0.7011	NPC84360
Intermediate Similarity	0.7011	NPC320630
Intermediate Similarity	0.7011	NPC281296
Intermediate Similarity	0.7011	NPC107668
Intermediate Similarity	0.7011	NPC7563
Intermediate Similarity	0.7011	NPC116177
Intermediate Similarity	0.701	NPC20546
Intermediate Similarity	0.701	NPC213698
Intermediate Similarity	0.701	NPC318282
Intermediate Similarity	0.701	NPC469599
Intermediate Similarity	0.701	NPC173875
Intermediate Similarity	0.701	NPC476174
Intermediate Similarity	0.701	NPC170120
Intermediate Similarity	0.701	NPC469995
Intermediate Similarity	0.701	NPC472932
Intermediate Similarity	0.701	NPC174948
Intermediate Similarity	0.7	NPC99411
Intermediate Similarity	0.7	NPC189972
Intermediate Similarity	0.7	NPC150923
Intermediate Similarity	0.7	NPC133844
Intermediate Similarity	0.7	NPC309300
Intermediate Similarity	0.7	NPC89555
Remote Similarity	0.6989	NPC167877
Remote Similarity	0.6989	NPC45957
Remote Similarity	0.6989	NPC86005
Remote Similarity	0.6989	NPC477959
Remote Similarity	0.6989	NPC471657
Remote Similarity	0.6989	NPC317590
Remote Similarity	0.6988	NPC469677
Remote Similarity	0.6988	NPC236208
Remote Similarity	0.6979	NPC66429
Remote Similarity	0.6979	NPC206810
Remote Similarity	0.6979	NPC37816
Remote Similarity	0.6979	NPC470376
Remote Similarity	0.6979	NPC470375
Remote Similarity	0.6979	NPC152897
Remote Similarity	0.697	NPC186810
Remote Similarity	0.697	NPC471610
Remote Similarity	0.697	NPC221615
Remote Similarity	0.6962	NPC271282
Remote Similarity	0.6962	NPC66460
Remote Similarity	0.6962	NPC321838
Remote Similarity	0.6962	NPC325929
Remote Similarity	0.6957	NPC474083
Remote Similarity	0.6957	NPC283733
Remote Similarity	0.6957	NPC471224

Drug Structure

NPD5331 OpenBabel08211706322D 29 30 0 0 1 0 0 0 0 0999 V2000 0.8482 -6.5093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6107 -2.2978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3619 -5.6670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1244 -4.8247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1273 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0523 1.2779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6107 -3.9824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9250 0.0260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2545 2.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0059 -1.6812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8482 -2.1675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4602 0.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4602 -0.8389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4922 0.8649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1244 -3.1401 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9524 0.0260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4764 0.8649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4922 -0.8389 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4764 -0.8389 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8482 -3.1401 0.0000 C 0 0 2 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 6.1795 2.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6905 -3.6264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9726 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9023 1.8790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3817 3.4812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5328 -3.1401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1748 -0.9514 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3067 3.7817 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 15 1 0 0 0 0 3 4 3 0 0 0 0 4 7 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 22 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 17 12 1 6 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 13 1 6 0 0 0 20 11 1 1 0 0 0 20 23 1 0 0 0 0 21 24 1 6 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 26 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000273
DrugBank
ChEMBL
IUPHAR/BPS	1895
PharmaGKB
KEGG Drug
PubChem CID	6435378
ChEBI
CAS Number

Drug Properties

Molecular Weight	360.23
ALogP	1.1479
MLogP	3.44
XLogP	3.192
HDA	4
HBD	3
Rotatable Bonds	12
TPSA	77.76
RO5 Violation	0