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:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6664

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	108799
0.1-0.2	99494
0.2-0.3	3266
0.3-0.4	136
0.4-0.5	39
0.5-0.6	6
0.6-0.7	0
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	0.5375	NPC56765
Remote Similarity	0.5375	NPC175190
Remote Similarity	0.5375	NPC506981
Remote Similarity	0.5375	NPC602380
Remote Similarity	0.5119	NPC586903
Remote Similarity	0.5119	NPC603365

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