NPASS drugs

Drug Information

Drug ID:	NPD6338
Drug Name:	Nefazodone
Molecular Formula:	C25H32ClN5O2
Canonical SMILES:	CCc1nn(c(=O)n1CCOc1ccccc1)CCCN1CCN(CC1)c1cccc(c1)Cl
Standard InCHI:	InChI=1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3
Standard InCHIKey:	VRBKIVRKKCLPHA-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6338

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	339
0.1-0.2	4641
0.2-0.3	8421
0.3-0.4	10176
0.4-0.5	6232
0.5-0.6	1064
0.6-0.7	16
0.7-0.8	1
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

Similarity Level	Similarity Score	Natural Product ID
Intermediate Similarity	0.7345	NPC315257
Remote Similarity	0.6951	NPC228206
Remote Similarity	0.6622	NPC471614
Remote Similarity	0.6341	NPC198401
Remote Similarity	0.633	NPC197141
Remote Similarity	0.6298	NPC476462
Remote Similarity	0.6284	NPC473874
Remote Similarity	0.6256	NPC471648
Remote Similarity	0.623	NPC260601
Remote Similarity	0.6229	NPC56271
Remote Similarity	0.62	NPC118776
Remote Similarity	0.6175	NPC168750
Remote Similarity	0.6133	NPC476475
Remote Similarity	0.6127	NPC232872
Remote Similarity	0.6068	NPC471593
Remote Similarity	0.6051	NPC254700
Remote Similarity	0.6019	NPC110741
Remote Similarity	0.5982	NPC242923
Remote Similarity	0.5981	NPC311357
Remote Similarity	0.5978	NPC189724
Remote Similarity	0.5978	NPC212850
Remote Similarity	0.5978	NPC83289
Remote Similarity	0.5943	NPC315632
Remote Similarity	0.5936	NPC247298
Remote Similarity	0.593	NPC85482
Remote Similarity	0.5916	NPC13397
Remote Similarity	0.5912	NPC297584
Remote Similarity	0.5909	NPC1527
Remote Similarity	0.5907	NPC52801
Remote Similarity	0.5879	NPC29650
Remote Similarity	0.5873	NPC245974
Remote Similarity	0.5872	NPC194699
Remote Similarity	0.5872	NPC219350
Remote Similarity	0.5868	NPC95977
Remote Similarity	0.5858	NPC264782
Remote Similarity	0.5856	NPC208022
Remote Similarity	0.5856	NPC471663
Remote Similarity	0.5854	NPC469831
Remote Similarity	0.5853	NPC473422
Remote Similarity	0.5847	NPC138365
Remote Similarity	0.5847	NPC237227
Remote Similarity	0.5838	NPC475998
Remote Similarity	0.5825	NPC469829
Remote Similarity	0.582	NPC9373
Remote Similarity	0.5816	NPC285635
Remote Similarity	0.5813	NPC220560
Remote Similarity	0.5806	NPC473460
Remote Similarity	0.5802	NPC280638
Remote Similarity	0.58	NPC477888
Remote Similarity	0.5796	NPC308906
Remote Similarity	0.5787	NPC191863
Remote Similarity	0.5787	NPC133470
Remote Similarity	0.5787	NPC289776
Remote Similarity	0.5782	NPC79213
Remote Similarity	0.5769	NPC274732
Remote Similarity	0.5766	NPC277306
Remote Similarity	0.5766	NPC469442
Remote Similarity	0.5765	NPC301163
Remote Similarity	0.5764	NPC290069
Remote Similarity	0.5763	NPC255253
Remote Similarity	0.5762	NPC473569
Remote Similarity	0.5758	NPC257851
Remote Similarity	0.5753	NPC204156
Remote Similarity	0.5748	NPC314948
Remote Similarity	0.5746	NPC473987
Remote Similarity	0.5742	NPC469830
Remote Similarity	0.5728	NPC219963
Remote Similarity	0.5721	NPC476518
Remote Similarity	0.5714	NPC473006
Remote Similarity	0.5714	NPC25539
Remote Similarity	0.5714	NPC26850
Remote Similarity	0.5707	NPC315498
Remote Similarity	0.5707	NPC177404
Remote Similarity	0.5707	NPC230942
Remote Similarity	0.57	NPC314659
Remote Similarity	0.57	NPC471785
Remote Similarity	0.5695	NPC471532
Remote Similarity	0.5694	NPC87391
Remote Similarity	0.5693	NPC14651
Remote Similarity	0.5693	NPC121658
Remote Similarity	0.5693	NPC258773
Remote Similarity	0.5687	NPC174629
Remote Similarity	0.5686	NPC473432
Remote Similarity	0.568	NPC70092
Remote Similarity	0.5676	NPC471561
Remote Similarity	0.5674	NPC478049
Remote Similarity	0.566	NPC475411
Remote Similarity	0.5652	NPC197335
Remote Similarity	0.5652	NPC184437
Remote Similarity	0.5652	NPC266551
Remote Similarity	0.5652	NPC161887
Remote Similarity	0.565	NPC24954
Remote Similarity	0.5646	NPC20249
Remote Similarity	0.5646	NPC315542
Remote Similarity	0.5642	NPC470586
Remote Similarity	0.5641	NPC26872
Remote Similarity	0.5641	NPC471132
Remote Similarity	0.5639	NPC244425
Remote Similarity	0.5639	NPC15384
Remote Similarity	0.5639	NPC471197
Remote Similarity	0.5634	NPC473004
Remote Similarity	0.5634	NPC204970
Remote Similarity	0.5634	NPC469961
Remote Similarity	0.5631	NPC287208
Remote Similarity	0.5622	NPC187145
Remote Similarity	0.5622	NPC157931
Remote Similarity	0.5614	NPC471198
Remote Similarity	0.5611	NPC250476
Remote Similarity	0.5611	NPC471736
Remote Similarity	0.5605	NPC469589
Remote Similarity	0.56	NPC118511

Drug Structure

NPD6338 OpenBabel08211709092D 33 36 0 0 0 0 0 0 0 0999 V2000 3.1650 1.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5772 0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8742 3.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4675 2.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2865 4.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4730 2.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2919 4.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4894 2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4839 2.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8852 3.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 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 -0.6386 1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8907 3.1341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 31 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 30 1 0 0 0 0 19 33 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 22 29 1 0 0 0 0 23 33 1 0 0 0 0 24 27 2 0 0 0 0 24 30 1 0 0 0 0 25 30 1 0 0 0 0 25 31 1 0 0 0 0 25 32 2 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000042
DrugBank	DB01149
ChEMBL	CHEMBL623
IUPHAR/BPS	7247
PharmaGKB	PA450603
KEGG Drug
PubChem CID	4449
ChEBI	7494
CAS Number	83366-66-9

Drug Properties

Molecular Weight	469.22
ALogP	-0.0855
MLogP	3.33
XLogP	4.993
HDA	6
HBD	0
Rotatable Bonds	12
TPSA	51.62
RO5 Violation	0