NPASS Natural Product

Natural Product: NPC471597

Natural Product ID:	NPC471597
Common Name:	Iromycin E
IUPAC Name:	6-[(2E,5E)-3,7-dimethylocta-2,5-dienyl]-4,5-dihydroxy-3-methyl-5-propylpyridin-2-one
Synonyms:
Molecular Formula:	C19H29NO3
Standard InCHIKey:	YZSSUVKYULNCGU-ACLLVWJRSA-N
Standard InCHI:	InChI=1S/C19H29NO3/c1-6-12-19(23)16(20-18(22)15(5)17(19)21)11-10-14(4)9-7-8-13(2)3/h7-8,10,13,21,23H,6,9,11-12H2,1-5H3/b8-7+,14-10+
Canonical SMILES:	CCCC1(O)C(=NC(=O)C(=C1O)C)C/C=C(/C/C=C/C(C)C)C
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
NPO33217	streptomyces sp. dra 17	Species	Streptomycetaceae	Bacteria				PMID[18054490]

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5098	Protein Complex	Mitochondrial complex I; NADH oxidoreductase	Bos taurus	IC50	>	25300	nM	11141104

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 NPC471597 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	42
0.1-0.2	267
0.2-0.3	5182
0.3-0.4	17106
0.4-0.5	7242
0.5-0.6	1023
0.6-0.7	26
0.7-0.8	1
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
0.7241	Intermediate Similarity	NPC471595
0.6591	Remote Similarity	NPC314854
0.6591	Remote Similarity	NPC313911
0.6559	Remote Similarity	NPC472614
0.6489	Remote Similarity	NPC316186
0.6442	Remote Similarity	NPC251330
0.6346	Remote Similarity	NPC154601
0.6346	Remote Similarity	NPC271269
0.63	Remote Similarity	NPC265662
0.625	Remote Similarity	NPC21848
0.625	Remote Similarity	NPC124849
0.6235	Remote Similarity	NPC4706
0.6224	Remote Similarity	NPC472613
0.6196	Remote Similarity	NPC224072
0.618	Remote Similarity	NPC477484
0.618	Remote Similarity	NPC477486
0.6162	Remote Similarity	NPC116930
0.6125	Remote Similarity	NPC6795
0.6122	Remote Similarity	NPC314500
0.6122	Remote Similarity	NPC472264
0.6087	Remote Similarity	NPC477582
0.6047	Remote Similarity	NPC203819
0.6044	Remote Similarity	NPC477485
0.6038	Remote Similarity	NPC472615
0.6023	Remote Similarity	NPC288086
0.6022	Remote Similarity	NPC477583
0.6022	Remote Similarity	NPC477581
0.5974	Remote Similarity	NPC474127
0.5962	Remote Similarity	NPC175531
0.5952	Remote Similarity	NPC187315
0.5943	Remote Similarity	NPC472616
0.593	Remote Similarity	NPC471022
0.593	Remote Similarity	NPC136473
0.5914	Remote Similarity	NPC275766
0.5909	Remote Similarity	NPC314678
0.5909	Remote Similarity	NPC153660
0.5905	Remote Similarity	NPC469598
0.5882	Remote Similarity	NPC106613
0.5872	Remote Similarity	NPC133729
0.5865	Remote Similarity	NPC316730
0.5862	Remote Similarity	NPC316029
0.5862	Remote Similarity	NPC315597
0.5854	Remote Similarity	NPC273614
0.5851	Remote Similarity	NPC39966
0.5849	Remote Similarity	NPC318544
0.5843	Remote Similarity	NPC469835
0.5833	Remote Similarity	NPC471566
0.5833	Remote Similarity	NPC471556
0.5825	Remote Similarity	NPC167380
0.5818	Remote Similarity	NPC122926
0.5818	Remote Similarity	NPC113012
0.5814	Remote Similarity	NPC117804
0.5814	Remote Similarity	NPC313444
0.581	Remote Similarity	NPC313234
0.5802	Remote Similarity	NPC312826
0.5795	Remote Similarity	NPC126061
0.5795	Remote Similarity	NPC95863
0.5795	Remote Similarity	NPC469836
0.5794	Remote Similarity	NPC470073
0.5789	Remote Similarity	NPC44261
0.5784	Remote Similarity	NPC189764
0.578	Remote Similarity	NPC140251
0.578	Remote Similarity	NPC307903
0.5766	Remote Similarity	NPC170375
0.5765	Remote Similarity	NPC137163
0.5765	Remote Similarity	NPC267027
0.5765	Remote Similarity	NPC315115
0.5765	Remote Similarity	NPC129995
0.5765	Remote Similarity	NPC315141
0.5761	Remote Similarity	NPC469492
0.575	Remote Similarity	NPC245650
0.5747	Remote Similarity	NPC151481
0.5747	Remote Similarity	NPC103712
0.5747	Remote Similarity	NPC291196
0.5732	Remote Similarity	NPC130807
0.573	Remote Similarity	NPC186042
0.573	Remote Similarity	NPC201562
0.573	Remote Similarity	NPC29542
0.573	Remote Similarity	NPC323437
0.5729	Remote Similarity	NPC477199
0.5728	Remote Similarity	NPC121857
0.5728	Remote Similarity	NPC247220
0.5714	Remote Similarity	NPC150162
0.5714	Remote Similarity	NPC476269
0.5714	Remote Similarity	NPC294358
0.5714	Remote Similarity	NPC40417
0.5714	Remote Similarity	NPC68014
0.5701	Remote Similarity	NPC293299
0.5701	Remote Similarity	NPC474563
0.5701	Remote Similarity	NPC45365
0.57	Remote Similarity	NPC473056
0.5699	Remote Similarity	NPC469617
0.5699	Remote Similarity	NPC469517
0.5698	Remote Similarity	NPC278895
0.5696	Remote Similarity	NPC297020
0.5696	Remote Similarity	NPC227135
0.5696	Remote Similarity	NPC273023
0.5682	Remote Similarity	NPC315285
0.5679	Remote Similarity	NPC325734
0.5679	Remote Similarity	NPC181872
0.5679	Remote Similarity	NPC210999
0.5673	Remote Similarity	NPC52820
0.5667	Remote Similarity	NPC470686
0.5667	Remote Similarity	NPC122244
0.5663	Remote Similarity	NPC269737
0.5663	Remote Similarity	NPC29468
0.5663	Remote Similarity	NPC64985
0.5657	Remote Similarity	NPC34754
0.5652	Remote Similarity	NPC476007
0.5652	Remote Similarity	NPC315394
0.5648	Remote Similarity	NPC469604
0.5647	Remote Similarity	NPC470688
0.5647	Remote Similarity	NPC471565
0.5647	Remote Similarity	NPC477525
0.5641	Remote Similarity	NPC303672
0.5636	Remote Similarity	NPC470072
0.5632	Remote Similarity	NPC249713
0.5632	Remote Similarity	NPC272961
0.5631	Remote Similarity	NPC205546
0.5631	Remote Similarity	NPC233273
0.5631	Remote Similarity	NPC50902
0.5625	Remote Similarity	NPC228638
0.5625	Remote Similarity	NPC475083
0.5625	Remote Similarity	NPC4881
0.5625	Remote Similarity	NPC261158
0.5625	Remote Similarity	NPC24216
0.5625	Remote Similarity	NPC306420
0.5625	Remote Similarity	NPC104138
0.5618	Remote Similarity	NPC67076
0.5618	Remote Similarity	NPC319163
0.5614	Remote Similarity	NPC103391
0.5614	Remote Similarity	NPC476814
0.5614	Remote Similarity	NPC476813
0.5614	Remote Similarity	NPC472536
0.561	Remote Similarity	NPC278202
0.561	Remote Similarity	NPC74617
0.561	Remote Similarity	NPC150505
0.561	Remote Similarity	NPC475931
0.5604	Remote Similarity	NPC166018
0.5604	Remote Similarity	NPC169056
0.5604	Remote Similarity	NPC225665

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471597 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	260
0.2-0.3	3329
0.3-0.4	4579
0.4-0.5	844
0.5-0.6	77
0.6-0.7	7
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
0.6282	Remote Similarity	NPD570	Approved
0.625	Remote Similarity	NPD835	Approved
0.625	Remote Similarity	NPD834	Approved
0.6203	Remote Similarity	NPD571	Approved
0.6118	Remote Similarity	NPD1082	Approved
0.6118	Remote Similarity	NPD791	Approved
0.6118	Remote Similarity	NPD15	Approved
0.5889	Remote Similarity	NPD1346	Approved
0.5823	Remote Similarity	NPD273	Approved
0.5795	Remote Similarity	NPD816	Approved
0.5795	Remote Similarity	NPD815	Approved
0.5783	Remote Similarity	NPD833	Approved
0.5783	Remote Similarity	NPD832	Approved
0.5766	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6404	Discontinued
0.5714	Remote Similarity	NPD277	Approved
0.5652	Remote Similarity	NPD836	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD9575	Approved
0.5625	Remote Similarity	NPD7116	Clinical (unspecified phase)

Structure

NPC471597 OpenBabel07101719512D 23 23 0 0 1 0 0 0 0 0999 V2000 -2.7979 -2.0176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0908 -2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -1.1248 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 0.0000 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 3 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 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 -0.8912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	54732500
ChEMBL	CHEMBL272356
ZINC

Physicochemical Properties

Molecular Weight:	319.21
ALogP:	1.0604
MLogP:	3.11
XLogP:	4.611
# Rotatable Bonds:	14
Polar Surface Area:	69.89
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	23

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