NPASS Natural Product

Natural Product: NPC226982

Natural Product ID:	NPC226982
Common Name:	Pecilocin
IUPAC Name:	1-[(2E,4E,6E,8R)-8-hydroxy-6-methyldodeca-2,4,6-trienoyl]pyrrolidin-2-one
Synonyms:	Pecilocin; Variotin
Molecular Formula:	C17H25NO3
Standard InCHIKey:	ZYPGADGCNXOUJP-CXVPHVKISA-N
Standard InCHI:	InChI=1S/C17H25NO3/c1-3-4-9-15(19)13-14(2)8-5-6-10-16(20)18-12-7-11-17(18)21/h5-6,8,10,13,15,19H,3-4,7,9,11-12H2,1-2H3/b8-5+,10-6+,14-13+/t15-/m1/s1
Canonical SMILES:	CCCC[C@H](/C=C(/C=C/C=C/C(=O)N1CCCC1=O)C)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32757	aspergillus viridi-nutans	Species	Aspergillaceae	Eukaryota				PMID[10924177]
NPO32913	paecilomyces formosus	Species	Thermoascaceae	Eukaryota				PMID[24411199]

Biological Activity

Activity Type	# Activity
IC50	26
MIC	4

Activity Type	# Activity
Individual Protein	16
Organism	4
Others	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	200000	nM	20350944
NPT6429	Individual Protein	DNA polymerase alpha catalytic subunit	Drosophila melanogaster	IC50	>	200000	nM	10924160
NPT6320	Individual Protein	DNA polymerase delta catalytic subunit	Drosophila melanogaster	IC50	>	200000	nM	10924160
NPT6594	Individual Protein	DNA-directed RNA polymerase	Enterobacteria phage T7	IC50	>	200000	nM	16933872
NPT6383	Individual Protein	Inosine-5'-monophosphate dehydrogenase 2	Mus musculus	IC50	>	200000	nM	16933872
NPT3656	Organism	Paecilomyces variotii	Paecilomyces variotii	MIC	=	1	ug/ml	26727375
NPT3659	Organism	Eremothecium coryli	Eremothecium coryli	MIC	=	1	ug/ml	23805995
NPT6225	Organism	Nadsonia fulvescens	Nadsonia fulvescens	MIC	=	1	ug/ml	21435874
NPT6333	Individual Protein	DNA polymerase	Enterobacteria phage T4	IC50	>	200000	nM	20624681
NPT2	Others	Unspecified		IC50	>	200000	nM	20405881
NPT26	Individual Protein	Reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200000	nM	20405881
NPT6223	Individual Protein	Polynucleotide kinase	Enterobacteria phage T4	IC50	>	200000	nM	15974609
NPT6348	Individual Protein	DNA polymerase lambda	Mus musculus	IC50	>	200000	nM	17157006
NPT2	Others	Unspecified		IC50	>	200000	nM	24210499
NPT6396	Individual Protein	DNA-directed DNA/RNA polymerase mu	Homo sapiens	IC50	>	200000	nM	10.6019/CHEMBL1201861
NPT3628	Organism	Rhodotorula glutinis	Rhodotorula glutinis	MIC	=	1	ug/ml	DrugMatrix in vivo data: Pathology
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	IC50	>	200000	nM	19035792
NPT2	Others	Unspecified		IC50	>	200000	nM	19035792
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	IC50	>	200000	nM	19035792
NPT4232	Individual Protein	DNA polymerase delta subunit 1	Homo sapiens	IC50	>	200000	nM	22934671
NPT2	Others	Unspecified		IC50	>	200000	nM	22934671
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	>	200000	nM	22934671
NPT4538	Individual Protein	DNA nucleotidylexotransferase	Bos taurus	IC50	>	200000	nM	17417907
NPT2	Others	Unspecified		IC50	>	200000	nM	17417907
NPT2	Others	Unspecified		IC50	>	200000	nM	25302529
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	IC50	>	200000	nM	8759172
NPT2	Others	Unspecified		IC50	>	200000	nM	DrugMatrix in vitro pharmacology data
NPT4478	Individual Protein	Deoxyribonuclease-1	Bos taurus	IC50	>	200000	nM	17850057
NPT2	Others	Unspecified		IC50	>	200000	nM	22584254

Similar Natural Products in NPASS

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

● The left chart: Distribution of similarity level between NPC226982 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	43
0.1-0.2	239
0.2-0.3	8177
0.3-0.4	16030
0.4-0.5	5396
0.5-0.6	931
0.6-0.7	64
0.7-0.8	6
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC277341
0.8659	High Similarity	NPC475975
0.8049	Intermediate Similarity	NPC471768
0.7922	Intermediate Similarity	NPC96272
0.7333	Intermediate Similarity	NPC133923
0.72	Intermediate Similarity	NPC385
0.7143	Intermediate Similarity	NPC34672
0.7143	Intermediate Similarity	NPC252684
0.7126	Intermediate Similarity	NPC209232
0.6977	Remote Similarity	NPC46268
0.6837	Remote Similarity	NPC52820
0.6832	Remote Similarity	NPC474828
0.6832	Remote Similarity	NPC474827
0.6832	Remote Similarity	NPC68001
0.6832	Remote Similarity	NPC199831
0.6706	Remote Similarity	NPC326126
0.6634	Remote Similarity	NPC77703
0.6596	Remote Similarity	NPC324506
0.6593	Remote Similarity	NPC473810
0.6582	Remote Similarity	NPC42477
0.6571	Remote Similarity	NPC474099
0.6569	Remote Similarity	NPC474244
0.6548	Remote Similarity	NPC471022
0.6535	Remote Similarity	NPC316730
0.6531	Remote Similarity	NPC313265
0.6481	Remote Similarity	NPC314550
0.6471	Remote Similarity	NPC97614
0.6471	Remote Similarity	NPC188785
0.6458	Remote Similarity	NPC81195
0.6392	Remote Similarity	NPC53240
0.6383	Remote Similarity	NPC319913
0.6353	Remote Similarity	NPC90782
0.6353	Remote Similarity	NPC236208
0.6346	Remote Similarity	NPC318544
0.6341	Remote Similarity	NPC206660
0.6339	Remote Similarity	NPC470300
0.6316	Remote Similarity	NPC130436
0.6316	Remote Similarity	NPC469860
0.6316	Remote Similarity	NPC469861
0.6316	Remote Similarity	NPC322672
0.6293	Remote Similarity	NPC36254
0.6286	Remote Similarity	NPC470073
0.6282	Remote Similarity	NPC472808
0.6282	Remote Similarity	NPC324224
0.6262	Remote Similarity	NPC470072
0.625	Remote Similarity	NPC473525
0.6235	Remote Similarity	NPC23721
0.6214	Remote Similarity	NPC474985
0.6203	Remote Similarity	NPC268185
0.6176	Remote Similarity	NPC476344
0.6139	Remote Similarity	NPC469739
0.6139	Remote Similarity	NPC150041
0.6136	Remote Similarity	NPC252503
0.6118	Remote Similarity	NPC106613
0.6104	Remote Similarity	NPC217188
0.6071	Remote Similarity	NPC272166
0.6067	Remote Similarity	NPC470992
0.6067	Remote Similarity	NPC470993
0.6067	Remote Similarity	NPC227396
0.6061	Remote Similarity	NPC17143
0.6061	Remote Similarity	NPC47230
0.6058	Remote Similarity	NPC233932
0.6058	Remote Similarity	NPC26597
0.6053	Remote Similarity	NPC476155
0.6053	Remote Similarity	NPC17581
0.6024	Remote Similarity	NPC471023
0.6019	Remote Similarity	NPC471447
0.6018	Remote Similarity	NPC66007
0.6	Remote Similarity	NPC144714
0.6	Remote Similarity	NPC470788
0.6	Remote Similarity	NPC100810
0.6	Remote Similarity	NPC469603
0.6	Remote Similarity	NPC71755
0.5981	Remote Similarity	NPC469604
0.5977	Remote Similarity	NPC143396
0.5977	Remote Similarity	NPC477688
0.5976	Remote Similarity	NPC327112
0.5976	Remote Similarity	NPC6795
0.5963	Remote Similarity	NPC207820
0.5955	Remote Similarity	NPC314678
0.5949	Remote Similarity	NPC317899
0.5922	Remote Similarity	NPC175614
0.5921	Remote Similarity	NPC225974
0.5909	Remote Similarity	NPC133700
0.5888	Remote Similarity	NPC476877
0.5882	Remote Similarity	NPC97580
0.5882	Remote Similarity	NPC474974
0.5862	Remote Similarity	NPC474823
0.5862	Remote Similarity	NPC309466
0.5854	Remote Similarity	NPC322002
0.5854	Remote Similarity	NPC318306
0.5843	Remote Similarity	NPC67076
0.5843	Remote Similarity	NPC95863
0.5843	Remote Similarity	NPC316185
0.5843	Remote Similarity	NPC319163
0.5833	Remote Similarity	NPC473737
0.5823	Remote Similarity	NPC189677
0.5823	Remote Similarity	NPC300121
0.5818	Remote Similarity	NPC476276
0.5814	Remote Similarity	NPC146811
0.5814	Remote Similarity	NPC129995
0.5814	Remote Similarity	NPC315141
0.5804	Remote Similarity	NPC168758
0.5804	Remote Similarity	NPC58281
0.5804	Remote Similarity	NPC47857
0.5804	Remote Similarity	NPC181510
0.5795	Remote Similarity	NPC475004
0.5794	Remote Similarity	NPC473289
0.5789	Remote Similarity	NPC267110
0.5789	Remote Similarity	NPC474984
0.5783	Remote Similarity	NPC305973
0.578	Remote Similarity	NPC472856
0.578	Remote Similarity	NPC476876
0.5778	Remote Similarity	NPC284006
0.5778	Remote Similarity	NPC238948
0.5778	Remote Similarity	NPC12815
0.5778	Remote Similarity	NPC26932
0.5778	Remote Similarity	NPC215745
0.5747	Remote Similarity	NPC98329
0.5747	Remote Similarity	NPC7392
0.5741	Remote Similarity	NPC6271
0.5714	Remote Similarity	NPC474545
0.5714	Remote Similarity	NPC315843
0.5714	Remote Similarity	NPC288381
0.5714	Remote Similarity	NPC470994
0.5714	Remote Similarity	NPC269737
0.5714	Remote Similarity	NPC241426
0.5714	Remote Similarity	NPC20934
0.5714	Remote Similarity	NPC26810
0.5714	Remote Similarity	NPC91036
0.57	Remote Similarity	NPC155230
0.5698	Remote Similarity	NPC245947
0.5698	Remote Similarity	NPC136164
0.5698	Remote Similarity	NPC323045
0.5698	Remote Similarity	NPC255863
0.5698	Remote Similarity	NPC477525
0.5698	Remote Similarity	NPC317881
0.5696	Remote Similarity	NPC61177
0.5688	Remote Similarity	NPC64168
0.5688	Remote Similarity	NPC133420
0.5684	Remote Similarity	NPC476560
0.5667	Remote Similarity	NPC293114
0.5663	Remote Similarity	NPC322186
0.5663	Remote Similarity	NPC329249
0.5657	Remote Similarity	NPC202056
0.5656	Remote Similarity	NPC262880
0.5656	Remote Similarity	NPC247902
0.5652	Remote Similarity	NPC478196
0.5652	Remote Similarity	NPC103391
0.5652	Remote Similarity	NPC478191
0.5652	Remote Similarity	NPC478192
0.5652	Remote Similarity	NPC161038
0.5652	Remote Similarity	NPC472536
0.5652	Remote Similarity	NPC478195
0.5652	Remote Similarity	NPC478193
0.5652	Remote Similarity	NPC260396
0.5652	Remote Similarity	NPC478194
0.5647	Remote Similarity	NPC477106
0.5647	Remote Similarity	NPC322457
0.5647	Remote Similarity	NPC68110
0.5645	Remote Similarity	NPC41162
0.5641	Remote Similarity	NPC474495
0.5641	Remote Similarity	NPC59408
0.5641	Remote Similarity	NPC473672
0.5641	Remote Similarity	NPC71053
0.5638	Remote Similarity	NPC28529
0.5638	Remote Similarity	NPC473471
0.5636	Remote Similarity	NPC471259
0.5636	Remote Similarity	NPC476328
0.5632	Remote Similarity	NPC37382
0.5632	Remote Similarity	NPC187315
0.5631	Remote Similarity	NPC304897
0.5631	Remote Similarity	NPC38172
0.5625	Remote Similarity	NPC21324
0.5625	Remote Similarity	NPC110732
0.5625	Remote Similarity	NPC322461
0.5625	Remote Similarity	NPC184473
0.5615	Remote Similarity	NPC315848
0.5615	Remote Similarity	NPC315210
0.5614	Remote Similarity	NPC474497
0.5614	Remote Similarity	NPC474995
0.5612	Remote Similarity	NPC161670
0.561	Remote Similarity	NPC245650
0.5607	Remote Similarity	NPC477964
0.56	Remote Similarity	NPC120335

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC226982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	65
0.1-0.2	188
0.2-0.3	3201
0.3-0.4	4520
0.4-0.5	1113
0.5-0.6	71
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.618	Remote Similarity	NPD1452	Discontinued
0.6075	Remote Similarity	NPD7333	Discontinued
0.6071	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD9137	Approved
0.5741	Remote Similarity	NPD2905	Discontinued
0.566	Remote Similarity	NPD211	Approved
0.566	Remote Similarity	NPD210	Approved

Structure

NPC226982 OpenBabel07101718302D 21 21 0 0 1 0 0 0 0 0999 V2000 -8.0926 -5.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1537 -1.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 -5.3495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5103 -4.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 -1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 -2.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9170 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3347 -2.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7469 -2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3292 -2.8180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 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 -6.7360 -1.9044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 14 1 0 0 0 0 3 4 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 8 2 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 15 19 1 1 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5282176
ChEMBL	CHEMBL486174
ZINC

Physicochemical Properties

Molecular Weight:	291.18
ALogP:	-0.5802
MLogP:	2.89
XLogP:	2.648
# Rotatable Bonds:	11
Polar Surface Area:	57.61
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	21

Download Data

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General Info & Identifiers & Properties
Structure MOL file
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