NPASS drugs

Drug Information

Drug ID:	NPD6664
Drug Name:	Cabergoline
Molecular Formula:	C26H37N5O2
Canonical SMILES:	C=CCN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N(C(=NCC)O)CCCN(C)C
Standard InCHI:	InChI=1S/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1
Standard InCHIKey:	KORNTPPJEAJQIU-KJXAQDMKSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6664

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	390
0.1-0.2	2474
0.2-0.3	13664
0.3-0.4	9877
0.4-0.5	1743
0.5-0.6	1360
0.6-0.7	975
0.7-0.8	388
0.8-0.85	19
0.85-0.9	0
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
Intermediate Similarity	0.8391	NPC56765
Intermediate Similarity	0.8315	NPC228835
Intermediate Similarity	0.8297	NPC11126
Intermediate Similarity	0.8268	NPC194411
Intermediate Similarity	0.8226	NPC94752
Intermediate Similarity	0.8182	NPC206819
Intermediate Similarity	0.8182	NPC318065
Intermediate Similarity	0.8172	NPC99939
Intermediate Similarity	0.8172	NPC308931
Intermediate Similarity	0.8142	NPC68354
Intermediate Similarity	0.8132	NPC37423
Intermediate Similarity	0.8132	NPC275305
Intermediate Similarity	0.8098	NPC215795
Intermediate Similarity	0.8098	NPC176199
Intermediate Similarity	0.8021	NPC477003
Intermediate Similarity	0.802	NPC473376
Intermediate Similarity	0.801	NPC153980
Intermediate Similarity	0.801	NPC6865
Intermediate Similarity	0.8	NPC213468
Intermediate Similarity	0.7989	NPC17059
Intermediate Similarity	0.7978	NPC41257
Intermediate Similarity	0.7978	NPC161861
Intermediate Similarity	0.796	NPC72956
Intermediate Similarity	0.7959	NPC300183
Intermediate Similarity	0.7944	NPC90723
Intermediate Similarity	0.7921	NPC286427
Intermediate Similarity	0.7917	NPC47190
Intermediate Similarity	0.7906	NPC95783
Intermediate Similarity	0.7884	NPC133003
Intermediate Similarity	0.7853	NPC213629
Intermediate Similarity	0.7845	NPC21174
Intermediate Similarity	0.7845	NPC271797
Intermediate Similarity	0.7841	NPC33421
Intermediate Similarity	0.7833	NPC215584
Intermediate Similarity	0.7833	NPC471194
Intermediate Similarity	0.7833	NPC471193
Intermediate Similarity	0.7833	NPC44773
Intermediate Similarity	0.7831	NPC21429
Intermediate Similarity	0.7805	NPC471192
Intermediate Similarity	0.7789	NPC317701
Intermediate Similarity	0.7778	NPC470205
Intermediate Similarity	0.7772	NPC476460
Intermediate Similarity	0.7766	NPC16659
Intermediate Similarity	0.7761	NPC54420
Intermediate Similarity	0.7751	NPC155444
Intermediate Similarity	0.7744	NPC195239
Intermediate Similarity	0.7744	NPC157828
Intermediate Similarity	0.7744	NPC294693
Intermediate Similarity	0.774	NPC24678
Intermediate Similarity	0.774	NPC105818
Intermediate Similarity	0.7736	NPC56109
Intermediate Similarity	0.7736	NPC191382
Intermediate Similarity	0.7716	NPC171317
Intermediate Similarity	0.7714	NPC314372
Intermediate Similarity	0.7713	NPC265710
Intermediate Similarity	0.7713	NPC248462
Intermediate Similarity	0.7707	NPC54744
Intermediate Similarity	0.7704	NPC11445
Intermediate Similarity	0.7701	NPC267885
Intermediate Similarity	0.7701	NPC190296
Intermediate Similarity	0.7685	NPC162860
Intermediate Similarity	0.7672	NPC91179
Intermediate Similarity	0.7668	NPC321708
Intermediate Similarity	0.7667	NPC51054
Intermediate Similarity	0.7663	NPC160105
Intermediate Similarity	0.7663	NPC49217
Intermediate Similarity	0.766	NPC84827
Intermediate Similarity	0.766	NPC14113
Intermediate Similarity	0.766	NPC145885
Intermediate Similarity	0.7654	NPC469786
Intermediate Similarity	0.7654	NPC25008
Intermediate Similarity	0.7654	NPC469760
Intermediate Similarity	0.7654	NPC469765
Intermediate Similarity	0.7654	NPC200214
Intermediate Similarity	0.7654	NPC469763
Intermediate Similarity	0.7654	NPC73952
Intermediate Similarity	0.7654	NPC259644
Intermediate Similarity	0.765	NPC476073
Intermediate Similarity	0.7647	NPC149155
Intermediate Similarity	0.7647	NPC293216
Intermediate Similarity	0.7647	NPC203468
Intermediate Similarity	0.7647	NPC110500
Intermediate Similarity	0.7644	NPC281049
Intermediate Similarity	0.7622	NPC78020
Intermediate Similarity	0.7622	NPC201700
Intermediate Similarity	0.7619	NPC126709
Intermediate Similarity	0.7619	NPC248041
Intermediate Similarity	0.7614	NPC470440
Intermediate Similarity	0.7611	NPC70922
Intermediate Similarity	0.7611	NPC75540
Intermediate Similarity	0.7611	NPC80597
Intermediate Similarity	0.7611	NPC211572
Intermediate Similarity	0.7611	NPC212376
Intermediate Similarity	0.7598	NPC478158
Intermediate Similarity	0.759	NPC117244
Intermediate Similarity	0.759	NPC473763
Intermediate Similarity	0.7588	NPC220797
Intermediate Similarity	0.7588	NPC153123
Intermediate Similarity	0.7588	NPC475914
Intermediate Similarity	0.7588	NPC268744
Intermediate Similarity	0.7588	NPC293917
Intermediate Similarity	0.7588	NPC474318
Intermediate Similarity	0.7588	NPC201266
Intermediate Similarity	0.7586	NPC469784
Intermediate Similarity	0.7586	NPC469768
Intermediate Similarity	0.7586	NPC469779
Intermediate Similarity	0.7586	NPC469767
Intermediate Similarity	0.7586	NPC469780
Intermediate Similarity	0.7586	NPC469783
Intermediate Similarity	0.7586	NPC469761
Intermediate Similarity	0.7568	NPC49954
Intermediate Similarity	0.7568	NPC474561
Intermediate Similarity	0.7568	NPC56233
Intermediate Similarity	0.7566	NPC240088
Intermediate Similarity	0.7566	NPC473380
Intermediate Similarity	0.7565	NPC235684
Intermediate Similarity	0.7565	NPC141612
Intermediate Similarity	0.7565	NPC17273
Intermediate Similarity	0.7565	NPC135601
Intermediate Similarity	0.756	NPC477714
Intermediate Similarity	0.755	NPC269203
Intermediate Similarity	0.755	NPC77241
Intermediate Similarity	0.755	NPC166209
Intermediate Similarity	0.755	NPC13456
Intermediate Similarity	0.7548	NPC470732
Intermediate Similarity	0.7548	NPC470731
Intermediate Similarity	0.7547	NPC64216
Intermediate Similarity	0.7543	NPC469766
Intermediate Similarity	0.7538	NPC324091
Intermediate Similarity	0.7538	NPC474389
Intermediate Similarity	0.7538	NPC329858
Intermediate Similarity	0.7529	NPC73767
Intermediate Similarity	0.7529	NPC110126
Intermediate Similarity	0.7527	NPC63751
Intermediate Similarity	0.7527	NPC469762
Intermediate Similarity	0.7526	NPC283219
Intermediate Similarity	0.7524	NPC320968
Intermediate Similarity	0.7514	NPC159856
Intermediate Similarity	0.75	NPC470203
Intermediate Similarity	0.75	NPC477004
Intermediate Similarity	0.75	NPC478157
Intermediate Similarity	0.75	NPC314603
Intermediate Similarity	0.7488	NPC75634
Intermediate Similarity	0.7487	NPC227582
Intermediate Similarity	0.7487	NPC167710
Intermediate Similarity	0.7487	NPC229332
Intermediate Similarity	0.7487	NPC300688
Intermediate Similarity	0.7486	NPC135141
Intermediate Similarity	0.7486	NPC92796
Intermediate Similarity	0.7475	NPC162730
Intermediate Similarity	0.7475	NPC474116
Intermediate Similarity	0.7474	NPC151939
Intermediate Similarity	0.7474	NPC284775
Intermediate Similarity	0.7474	NPC62749
Intermediate Similarity	0.7474	NPC111275
Intermediate Similarity	0.7473	NPC469785
Intermediate Similarity	0.7472	NPC143872
Intermediate Similarity	0.7462	NPC471386
Intermediate Similarity	0.7461	NPC165495
Intermediate Similarity	0.7459	NPC311276
Intermediate Similarity	0.745	NPC473640
Intermediate Similarity	0.7448	NPC470677
Intermediate Similarity	0.7447	NPC6982
Intermediate Similarity	0.7446	NPC470204
Intermediate Similarity	0.7444	NPC53947
Intermediate Similarity	0.7438	NPC98715
Intermediate Similarity	0.7435	NPC55772
Intermediate Similarity	0.743	NPC21605
Intermediate Similarity	0.743	NPC471957
Intermediate Similarity	0.7429	NPC477715
Intermediate Similarity	0.7426	NPC475506
Intermediate Similarity	0.7424	NPC304203
Intermediate Similarity	0.7415	NPC477065
Intermediate Similarity	0.7414	NPC84911
Intermediate Similarity	0.7414	NPC105127
Intermediate Similarity	0.7413	NPC100321
Intermediate Similarity	0.7409	NPC19679
Intermediate Similarity	0.7405	NPC282231
Intermediate Similarity	0.7405	NPC194881
Intermediate Similarity	0.7403	NPC470233
Intermediate Similarity	0.7398	NPC175474
Intermediate Similarity	0.7396	NPC477042
Intermediate Similarity	0.7389	NPC155143
Intermediate Similarity	0.7382	NPC59269
Intermediate Similarity	0.7376	NPC252338
Intermediate Similarity	0.7366	NPC471191
Intermediate Similarity	0.7366	NPC194640
Intermediate Similarity	0.7366	NPC40779
Intermediate Similarity	0.7363	NPC34837
Intermediate Similarity	0.7363	NPC131887
Intermediate Similarity	0.7363	NPC325903
Intermediate Similarity	0.7363	NPC265576
Intermediate Similarity	0.7361	NPC476491
Intermediate Similarity	0.736	NPC314333
Intermediate Similarity	0.7358	NPC191415
Intermediate Similarity	0.7356	NPC29886
Intermediate Similarity	0.7356	NPC96102
Intermediate Similarity	0.7356	NPC261195
Intermediate Similarity	0.7351	NPC279918
Intermediate Similarity	0.7351	NPC122141

Drug Structure

NPD6664 OpenBabel08211710072D 35 38 0 0 1 0 0 0 0 0999 V2000 0.8327 2.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7913 -1.3730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9586 1.0327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7915 -0.4108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8330 1.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9579 -1.8539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3762 -3.2001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2918 0.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5842 -2.7429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1679 -2.7429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 0.9622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1250 -0.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4584 -0.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -1.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5838 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1677 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7918 -0.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3760 -0.4569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7916 -1.3719 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5842 -1.8287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7922 -1.3715 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1680 -1.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7920 -0.4570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3759 -1.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6248 -1.8531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2914 -1.8535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1248 -1.3726 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9597 -1.3711 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9584 0.0705 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4582 -1.3722 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6246 -2.8153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2912 -2.8157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8829 -1.6183 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1243 -3.2970 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 6 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 11 1 0 0 0 0 6 27 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 22 2 0 0 0 0 11 30 1 0 0 0 0 12 29 1 0 0 0 0 13 31 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 30 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 1 0 0 0 20 21 1 0 0 0 0 20 24 2 0 0 0 0 21 14 1 1 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 15 1 6 0 0 0 23 30 1 0 0 0 0 25 31 1 0 0 0 0 25 32 2 0 0 0 0 26 27 2 3 0 0 0 26 31 1 0 0 0 0 26 33 1 0 0 0 0 28 34 1 0 0 0 0 33 35 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000251
DrugBank	DB00248
ChEMBL	CHEMBL1201087
IUPHAR/BPS	37
PharmaGKB	PA448708
KEGG Drug	D00987
PubChem CID	54746
ChEBI	3286
CAS Number	81409-90-7

Drug Properties

Molecular Weight	451.29
ALogP	-0.1694
MLogP	3.55
XLogP	2.765
HDA	7
HBD	2
Rotatable Bonds	14
TPSA	75.17
RO5 Violation	0