NPASS Natural Product

Natural Product: NPC79220

Natural Product ID:	NPC79220
Common Name:	Helipyrone
IUPAC Name:	6-ethyl-3-[(6-ethyl-4-hydroxy-5-methyl-2-oxopyran-3-yl)methyl]-4-hydroxy-5-methylpyran-2-one
Synonyms:	Helipyrone
Molecular Formula:	C17H20O6
Standard InCHIKey:	BYRZLWJKTOLLBX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H20O6/c1-5-12-8(3)14(18)10(16(20)22-12)7-11-15(19)9(4)13(6-2)23-17(11)21/h18-19H,5-7H2,1-4H3
Canonical SMILES:	CCc1oc(=O)c(c(c1C)O)Cc1c(=O)oc(c(c1O)C)CC
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
NPO25148.1	Helichrysum italicum	Under-species	NA	NA	Flowered aerial parts	Arzana, Sardinia	2010-JUL	PMID[23265253]
NPO32653	helichrysum italicum ssp. microphyllum	Species	Asteraceae	Eukaryota				PMID[17315926]

Biological Activity

Activity Type	# Activity
IC50	1
MIC	6

Activity Type	# Activity
Organism	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	DrugMatrix in vitro pharmacology data
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12	ug/ml	10.6019/CHEMBL1201861
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	17869103
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64	ug/ml	15165148
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128	ug/ml	17517847
NPT2	Others	Unspecified		IC50	=	8700	nM	10691728

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 NPC79220 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	79
0.1-0.2	1224
0.2-0.3	5075
0.3-0.4	14222
0.4-0.5	7849
0.5-0.6	2213
0.6-0.7	204
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7826	Intermediate Similarity	NPC471556
0.7826	Intermediate Similarity	NPC471566
0.7826	Intermediate Similarity	NPC471565
0.7812	Intermediate Similarity	NPC49028
0.7656	Intermediate Similarity	NPC154626
0.7639	Intermediate Similarity	NPC473277
0.75	Intermediate Similarity	NPC287705
0.746	Intermediate Similarity	NPC15129
0.7361	Intermediate Similarity	NPC132286
0.7308	Intermediate Similarity	NPC315765
0.7297	Intermediate Similarity	NPC315597
0.726	Intermediate Similarity	NPC238223
0.7222	Intermediate Similarity	NPC315115
0.72	Intermediate Similarity	NPC133098
0.7143	Intermediate Similarity	NPC15193
0.7121	Intermediate Similarity	NPC218486
0.7067	Intermediate Similarity	NPC315285
0.7067	Intermediate Similarity	NPC59558
0.7042	Intermediate Similarity	NPC2328
0.7042	Intermediate Similarity	NPC68110
0.7027	Intermediate Similarity	NPC313444
0.7015	Intermediate Similarity	NPC173157
0.7	Intermediate Similarity	NPC478233
0.6986	Remote Similarity	NPC470033
0.6962	Remote Similarity	NPC316324
0.6923	Remote Similarity	NPC478191
0.6923	Remote Similarity	NPC478196
0.6923	Remote Similarity	NPC478192
0.6923	Remote Similarity	NPC478193
0.6923	Remote Similarity	NPC478195
0.6923	Remote Similarity	NPC478194
0.6875	Remote Similarity	NPC264391
0.6842	Remote Similarity	NPC316029
0.6753	Remote Similarity	NPC178575
0.675	Remote Similarity	NPC315394
0.6705	Remote Similarity	NPC274075
0.6667	Remote Similarity	NPC475083
0.6667	Remote Similarity	NPC221763
0.6628	Remote Similarity	NPC186332
0.6628	Remote Similarity	NPC47220
0.6625	Remote Similarity	NPC271986
0.6623	Remote Similarity	NPC202011
0.662	Remote Similarity	NPC133600
0.6579	Remote Similarity	NPC477117
0.6571	Remote Similarity	NPC293437
0.6571	Remote Similarity	NPC249850
0.6571	Remote Similarity	NPC135863
0.6567	Remote Similarity	NPC191643
0.6528	Remote Similarity	NPC79756
0.6528	Remote Similarity	NPC429928
0.6517	Remote Similarity	NPC303451
0.6517	Remote Similarity	NPC6414
0.6512	Remote Similarity	NPC307112
0.6512	Remote Similarity	NPC242233
0.6479	Remote Similarity	NPC254095
0.6479	Remote Similarity	NPC189700
0.6456	Remote Similarity	NPC144419
0.6438	Remote Similarity	NPC217537
0.6437	Remote Similarity	NPC122502
0.6429	Remote Similarity	NPC150717
0.6429	Remote Similarity	NPC86948
0.642	Remote Similarity	NPC470705
0.6413	Remote Similarity	NPC170204
0.64	Remote Similarity	NPC282760
0.6375	Remote Similarity	NPC470686
0.6375	Remote Similarity	NPC177030
0.6364	Remote Similarity	NPC234084
0.6364	Remote Similarity	NPC126184
0.6364	Remote Similarity	NPC113370
0.6364	Remote Similarity	NPC476079
0.6364	Remote Similarity	NPC103743
0.6353	Remote Similarity	NPC10080
0.6353	Remote Similarity	NPC123908
0.6338	Remote Similarity	NPC283502
0.6329	Remote Similarity	NPC316185
0.6322	Remote Similarity	NPC471223
0.6322	Remote Similarity	NPC67081
0.6316	Remote Similarity	NPC469446
0.6316	Remote Similarity	NPC146811
0.631	Remote Similarity	NPC160582
0.6301	Remote Similarity	NPC309408
0.6296	Remote Similarity	NPC315552
0.6296	Remote Similarity	NPC260396
0.6292	Remote Similarity	NPC473658
0.6292	Remote Similarity	NPC26078
0.6286	Remote Similarity	NPC25038
0.6282	Remote Similarity	NPC236208
0.6282	Remote Similarity	NPC151481
0.6279	Remote Similarity	NPC16488
0.6279	Remote Similarity	NPC185256
0.6267	Remote Similarity	NPC173409
0.6267	Remote Similarity	NPC53136
0.6264	Remote Similarity	NPC114345
0.6264	Remote Similarity	NPC32552
0.6264	Remote Similarity	NPC6099
0.6264	Remote Similarity	NPC303230
0.625	Remote Similarity	NPC315395
0.625	Remote Similarity	NPC284006
0.625	Remote Similarity	NPC21946
0.625	Remote Similarity	NPC316426
0.625	Remote Similarity	NPC316851
0.625	Remote Similarity	NPC238948
0.625	Remote Similarity	NPC215745
0.625	Remote Similarity	NPC12815
0.625	Remote Similarity	NPC223679
0.6237	Remote Similarity	NPC469543
0.6234	Remote Similarity	NPC203335
0.6222	Remote Similarity	NPC307092
0.6222	Remote Similarity	NPC51358
0.622	Remote Similarity	NPC238554
0.622	Remote Similarity	NPC225022
0.6216	Remote Similarity	NPC151648
0.6216	Remote Similarity	NPC26810
0.6216	Remote Similarity	NPC68044
0.6207	Remote Similarity	NPC474251
0.6203	Remote Similarity	NPC476012
0.6203	Remote Similarity	NPC67183
0.6203	Remote Similarity	NPC476037
0.6197	Remote Similarity	NPC51846
0.6196	Remote Similarity	NPC282644
0.6196	Remote Similarity	NPC476049
0.6196	Remote Similarity	NPC29798
0.619	Remote Similarity	NPC469617
0.6184	Remote Similarity	NPC7940
0.6184	Remote Similarity	NPC273600
0.6184	Remote Similarity	NPC476589
0.6184	Remote Similarity	NPC478099
0.6184	Remote Similarity	NPC220766
0.6184	Remote Similarity	NPC478098
0.6184	Remote Similarity	NPC96414
0.6176	Remote Similarity	NPC43053
0.6173	Remote Similarity	NPC92558
0.6173	Remote Similarity	NPC476590
0.6173	Remote Similarity	NPC114727
0.6173	Remote Similarity	NPC315843
0.6164	Remote Similarity	NPC82465
0.6164	Remote Similarity	NPC329550
0.6154	Remote Similarity	NPC280374
0.6154	Remote Similarity	NPC474823
0.6154	Remote Similarity	NPC470032
0.6145	Remote Similarity	NPC228902
0.6145	Remote Similarity	NPC473825
0.6145	Remote Similarity	NPC68156
0.6145	Remote Similarity	NPC475711
0.6145	Remote Similarity	NPC24827
0.6143	Remote Similarity	NPC322461
0.6136	Remote Similarity	NPC474424
0.6133	Remote Similarity	NPC132243
0.6133	Remote Similarity	NPC155849
0.6133	Remote Similarity	NPC475073
0.6133	Remote Similarity	NPC473737
0.6125	Remote Similarity	NPC293114
0.6118	Remote Similarity	NPC474510
0.6111	Remote Similarity	NPC129150
0.6111	Remote Similarity	NPC294938
0.6104	Remote Similarity	NPC142423
0.6104	Remote Similarity	NPC191233
0.6104	Remote Similarity	NPC37382
0.6104	Remote Similarity	NPC201356
0.6104	Remote Similarity	NPC308294
0.6104	Remote Similarity	NPC248125
0.6098	Remote Similarity	NPC206507
0.6098	Remote Similarity	NPC147621
0.6098	Remote Similarity	NPC161038
0.6098	Remote Similarity	NPC210258
0.6098	Remote Similarity	NPC68624
0.6092	Remote Similarity	NPC52923
0.6092	Remote Similarity	NPC188717
0.6092	Remote Similarity	NPC211455
0.6087	Remote Similarity	NPC327760
0.6087	Remote Similarity	NPC472705
0.6087	Remote Similarity	NPC45579
0.6082	Remote Similarity	NPC469851
0.6081	Remote Similarity	NPC476585
0.6081	Remote Similarity	NPC130953
0.6081	Remote Similarity	NPC98519
0.6076	Remote Similarity	NPC475982
0.6076	Remote Similarity	NPC470693
0.6076	Remote Similarity	NPC475004
0.6076	Remote Similarity	NPC494
0.6071	Remote Similarity	NPC108816
0.6071	Remote Similarity	NPC93763
0.6071	Remote Similarity	NPC28049
0.6067	Remote Similarity	NPC234038
0.6067	Remote Similarity	NPC164393
0.6064	Remote Similarity	NPC272050
0.6053	Remote Similarity	NPC475618
0.6049	Remote Similarity	NPC185186
0.6049	Remote Similarity	NPC327383
0.6049	Remote Similarity	NPC329890
0.6049	Remote Similarity	NPC329914
0.6049	Remote Similarity	NPC287878
0.6044	Remote Similarity	NPC212598
0.6044	Remote Similarity	NPC87306
0.6026	Remote Similarity	NPC21998
0.6026	Remote Similarity	NPC478097
0.6026	Remote Similarity	NPC49863
0.6024	Remote Similarity	NPC16279
0.6024	Remote Similarity	NPC205615
0.6024	Remote Similarity	NPC4492

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC79220 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	106
0.1-0.2	2016
0.2-0.3	4317
0.3-0.4	2174
0.4-0.5	480
0.5-0.6	64
0.6-0.7	4
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
0.6543	Remote Similarity	NPD4756	Discovery
0.6349	Remote Similarity	NPD9411	Phase 1
0.6119	Remote Similarity	NPD4220	Pre-registration
0.6026	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD6927	Phase 3
0.5867	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.573	Remote Similarity	NPD6110	Phase 1
0.5714	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3704	Approved
0.5672	Remote Similarity	NPD4222	Approved
0.5667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6698	Approved
0.5638	Remote Similarity	NPD46	Approved

Structure

NPC79220 OpenBabel07101718242D 23 24 0 0 0 0 0 0 0 0999 V2000 6.6511 -2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6511 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6511 -1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8197 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1569 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8197 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9883 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1569 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9883 0.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4942 -1.4400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3255 -1.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9883 -1.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	54709865
ChEMBL	CHEMBL225422
ZINC

Physicochemical Properties

Molecular Weight:	320.13
ALogP:	0.1536
MLogP:	2.67
XLogP:	1.657
# Rotatable Bonds:	10
Polar Surface Area:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	23

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