NPASS drugs

Drug Information

Drug ID:	NPD4454
Drug Name:	Rafabegron
Molecular Formula:	C21H23ClN2O4
Canonical SMILES:	C[C@H](Cc1c[nH]c2c1cccc2OCC(=O)O)NC[C@@H](c1cccc(c1)Cl)O
Standard InCHI:	InChI=1S/C21H23ClN2O4/c1-13(23-11-18(25)14-4-2-5-16(22)9-14)8-15-10-24-21-17(15)6-3-7-19(21)28-12-20(26)27/h2-7,9-10,13,18,23-25H,8,11-12H2,1H3,(H,26,27)/t13-,18+/m1/s1
Standard InCHIKey:	FHEYFIGWYQJVDR-ACJLOTCBSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4454

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	284
0.1-0.2	1785
0.2-0.3	9710
0.3-0.4	4273
0.4-0.5	11344
0.5-0.6	2326
0.6-0.7	1057
0.7-0.8	111
0.8-0.85	0
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

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Similarity Level	Similarity Score	Natural Product ID
Intermediate Similarity	0.7964	NPC476287
Intermediate Similarity	0.7877	NPC475190
Intermediate Similarity	0.7812	NPC288349
Intermediate Similarity	0.7803	NPC266931
Intermediate Similarity	0.7717	NPC475774
Intermediate Similarity	0.7679	NPC26679
Intermediate Similarity	0.7655	NPC470799
Intermediate Similarity	0.7655	NPC8022
Intermediate Similarity	0.7639	NPC251090
Intermediate Similarity	0.7636	NPC245816

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Drug Structure

NPD4454 OpenBabel08211705262D 32 34 0 0 1 0 0 0 0 0999 V2000 3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1180 -2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 -2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 -2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8383 0.6203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4128 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -0.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5074 1.3634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -0.2024 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -0.2024 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 4.5468 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1984 2.3145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4855 1.1555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1473 -0.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 0.2976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.7024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1547 1.8986 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 14 1 0 0 0 0 5 16 2 0 0 0 0 6 17 1 0 0 0 0 7 19 2 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 12 20 1 0 0 0 0 12 28 1 0 0 0 0 13 1 1 6 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 18 11 1 1 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB016776
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	402.13
ALogP	-1.128
MLogP	3
XLogP	2.997
HDA	5
HBD	4
Rotatable Bonds	13
TPSA	94.58
RO5 Violation	0