NPASS Natural Product

Natural Product: NPC316730

Natural Product ID:	NPC316730
Common Name:	Militarinone E
IUPAC Name:	1,4-dihydroxy-5-[(4S)-4-hydroxycyclohexen-1-yl]-3-[(2E,4E,6E,8R,10R)-6,8,10-trimethyldodeca-2,4,6-trienoyl]pyridin-2-one
Synonyms:	Militarinone E
Molecular Formula:	C26H35NO5
Standard InCHIKey:	BFJKFLDLQKCOHR-BFIBXSCBSA-N
Standard InCHI:	InChI=1S/C26H35NO5/c1-5-17(2)14-19(4)15-18(3)8-6-7-9-23(29)24-25(30)22(16-27(32)26(24)31)20-10-12-21(28)13-11-20/h6-10,15-17,19,21,28,30,32H,5,11-14H2,1-4H3/b8-6+,9-7+,18-15+/t17-,19-,21-/m1/s1
Canonical SMILES:	CC[C@H](C[C@H](/C=C(/C=C/C=C/C(=O)c1c(O)c(cn(c1=O)O)C1=CC[C@H](CC1)O)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
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota				PMID[21158423]

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1590	nM	21158423
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	150000	nM	21158423
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	>	150000	nM	21158423
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	150000	nM	21158423

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 NPC316730 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	59
0.1-0.2	337
0.2-0.3	1948
0.3-0.4	14615
0.4-0.5	10814
0.5-0.6	3016
0.6-0.7	96
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC470073
0.9278	High Similarity	NPC318544
0.8725	High Similarity	NPC470072
0.7087	Intermediate Similarity	NPC473056
0.6975	Remote Similarity	NPC477140
0.6975	Remote Similarity	NPC477143
0.6952	Remote Similarity	NPC247316
0.6724	Remote Similarity	NPC44733
0.6667	Remote Similarity	NPC77703
0.6609	Remote Similarity	NPC476276
0.6581	Remote Similarity	NPC21713
0.6581	Remote Similarity	NPC475608
0.6562	Remote Similarity	NPC81092
0.6562	Remote Similarity	NPC103605
0.6545	Remote Similarity	NPC472166
0.6535	Remote Similarity	NPC226982
0.6535	Remote Similarity	NPC277341
0.6471	Remote Similarity	NPC473810
0.6446	Remote Similarity	NPC475642
0.6442	Remote Similarity	NPC2640
0.6436	Remote Similarity	NPC209232
0.6435	Remote Similarity	NPC476328
0.6429	Remote Similarity	NPC34672
0.6396	Remote Similarity	NPC265662
0.6356	Remote Similarity	NPC476290
0.63	Remote Similarity	NPC471061
0.6293	Remote Similarity	NPC472856
0.6286	Remote Similarity	NPC32037
0.6262	Remote Similarity	NPC316186
0.6262	Remote Similarity	NPC7280
0.6262	Remote Similarity	NPC229612
0.6261	Remote Similarity	NPC68001
0.6261	Remote Similarity	NPC199831
0.6261	Remote Similarity	NPC474827
0.6261	Remote Similarity	NPC474828
0.625	Remote Similarity	NPC52820
0.625	Remote Similarity	NPC476269
0.624	Remote Similarity	NPC475383
0.624	Remote Similarity	NPC156379
0.6239	Remote Similarity	NPC314500
0.6239	Remote Similarity	NPC251330
0.6228	Remote Similarity	NPC144714
0.6228	Remote Similarity	NPC100810
0.6228	Remote Similarity	NPC316250
0.6226	Remote Similarity	NPC322672
0.6214	Remote Similarity	NPC6663
0.621	Remote Similarity	NPC241050
0.619	Remote Similarity	NPC302360
0.6186	Remote Similarity	NPC220730
0.6168	Remote Similarity	NPC113370
0.6168	Remote Similarity	NPC103743
0.6168	Remote Similarity	NPC476079
0.6168	Remote Similarity	NPC473525
0.6161	Remote Similarity	NPC175614
0.6154	Remote Similarity	NPC271269
0.6154	Remote Similarity	NPC154601
0.6139	Remote Similarity	NPC46268
0.6139	Remote Similarity	NPC203403
0.6134	Remote Similarity	NPC21324
0.6132	Remote Similarity	NPC319913
0.6122	Remote Similarity	NPC95863
0.6117	Remote Similarity	NPC74086
0.6111	Remote Similarity	NPC60765
0.6106	Remote Similarity	NPC476344
0.6106	Remote Similarity	NPC91036
0.6106	Remote Similarity	NPC472167
0.6095	Remote Similarity	NPC16488
0.6095	Remote Similarity	NPC57370
0.6078	Remote Similarity	NPC231739
0.6078	Remote Similarity	NPC475994
0.6075	Remote Similarity	NPC316426
0.6075	Remote Similarity	NPC315395
0.6075	Remote Similarity	NPC472136
0.6071	Remote Similarity	NPC150041
0.6068	Remote Similarity	NPC133420
0.6055	Remote Similarity	NPC81195
0.6055	Remote Similarity	NPC471054
0.605	Remote Similarity	NPC307903
0.605	Remote Similarity	NPC140251
0.605	Remote Similarity	NPC474099
0.6048	Remote Similarity	NPC476190
0.604	Remote Similarity	NPC250621
0.6038	Remote Similarity	NPC475975
0.6036	Remote Similarity	NPC282644
0.6036	Remote Similarity	NPC29798
0.6034	Remote Similarity	NPC474244
0.6034	Remote Similarity	NPC128501
0.602	Remote Similarity	NPC318766
0.602	Remote Similarity	NPC203819
0.6019	Remote Similarity	NPC287079
0.6019	Remote Similarity	NPC241054
0.6019	Remote Similarity	NPC19900
0.6017	Remote Similarity	NPC472615
0.6	Remote Similarity	NPC47230
0.6	Remote Similarity	NPC19771
0.6	Remote Similarity	NPC158411
0.6	Remote Similarity	NPC477964
0.6	Remote Similarity	NPC224455
0.6	Remote Similarity	NPC38796
0.6	Remote Similarity	NPC17143
0.5984	Remote Similarity	NPC314550
0.5983	Remote Similarity	NPC474563
0.5982	Remote Similarity	NPC473162
0.5982	Remote Similarity	NPC474690
0.5982	Remote Similarity	NPC299100
0.5981	Remote Similarity	NPC187529
0.5981	Remote Similarity	NPC475614
0.5981	Remote Similarity	NPC15807
0.5981	Remote Similarity	NPC307112
0.5981	Remote Similarity	NPC242233
0.5981	Remote Similarity	NPC109528
0.5981	Remote Similarity	NPC76283
0.598	Remote Similarity	NPC315394
0.598	Remote Similarity	NPC82666
0.598	Remote Similarity	NPC97173
0.5966	Remote Similarity	NPC315531
0.5963	Remote Similarity	NPC472011
0.5963	Remote Similarity	NPC106051
0.5962	Remote Similarity	NPC476560
0.5948	Remote Similarity	NPC175531
0.5948	Remote Similarity	NPC469851
0.5946	Remote Similarity	NPC142838
0.5946	Remote Similarity	NPC32552
0.5946	Remote Similarity	NPC472010
0.5943	Remote Similarity	NPC477786
0.5943	Remote Similarity	NPC475083
0.5943	Remote Similarity	NPC477784
0.5943	Remote Similarity	NPC477785
0.5941	Remote Similarity	NPC474885
0.5941	Remote Similarity	NPC315552
0.5938	Remote Similarity	NPC137163
0.5932	Remote Similarity	NPC472616
0.5929	Remote Similarity	NPC180950
0.5926	Remote Similarity	NPC472974
0.5926	Remote Similarity	NPC203795
0.5922	Remote Similarity	NPC192006
0.5922	Remote Similarity	NPC478122
0.592	Remote Similarity	NPC271621
0.592	Remote Similarity	NPC59751
0.592	Remote Similarity	NPC27413
0.592	Remote Similarity	NPC235421
0.5909	Remote Similarity	NPC472983
0.5909	Remote Similarity	NPC472688
0.5909	Remote Similarity	NPC472676
0.5905	Remote Similarity	NPC275766
0.59	Remote Similarity	NPC186042
0.5888	Remote Similarity	NPC33913
0.5888	Remote Similarity	NPC472265
0.5882	Remote Similarity	NPC477708
0.5882	Remote Similarity	NPC469852
0.5878	Remote Similarity	NPC473249
0.5877	Remote Similarity	NPC250757
0.5877	Remote Similarity	NPC301534
0.5876	Remote Similarity	NPC96962
0.5876	Remote Similarity	NPC106613
0.5873	Remote Similarity	NPC471673
0.5872	Remote Similarity	NPC313658
0.5872	Remote Similarity	NPC324506
0.5872	Remote Similarity	NPC316138
0.5868	Remote Similarity	NPC133729
0.5865	Remote Similarity	NPC471597
0.5862	Remote Similarity	NPC185253
0.5862	Remote Similarity	NPC215253
0.5856	Remote Similarity	NPC265856
0.5856	Remote Similarity	NPC53240
0.5847	Remote Similarity	NPC320294
0.5842	Remote Similarity	NPC227396
0.5841	Remote Similarity	NPC78159
0.5841	Remote Similarity	NPC472977
0.5841	Remote Similarity	NPC474882
0.5841	Remote Similarity	NPC472976
0.5833	Remote Similarity	NPC470177
0.5833	Remote Similarity	NPC469853
0.5833	Remote Similarity	NPC176773
0.5833	Remote Similarity	NPC476426
0.5826	Remote Similarity	NPC99726
0.5826	Remote Similarity	NPC474938
0.5826	Remote Similarity	NPC474785
0.5826	Remote Similarity	NPC471694
0.5826	Remote Similarity	NPC241426
0.5826	Remote Similarity	NPC161147
0.5825	Remote Similarity	NPC476007
0.582	Remote Similarity	NPC469603
0.582	Remote Similarity	NPC328052
0.582	Remote Similarity	NPC477997
0.5816	Remote Similarity	NPC117804
0.581	Remote Similarity	NPC471514
0.5804	Remote Similarity	NPC472978
0.58	Remote Similarity	NPC67076
0.58	Remote Similarity	NPC319163
0.5798	Remote Similarity	NPC9436
0.5798	Remote Similarity	NPC469604
0.5794	Remote Similarity	NPC297398
0.5784	Remote Similarity	NPC171148
0.5784	Remote Similarity	NPC313179
0.5784	Remote Similarity	NPC69383
0.578	Remote Similarity	NPC186332
0.578	Remote Similarity	NPC118648
0.578	Remote Similarity	NPC183736
0.578	Remote Similarity	NPC194417

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC316730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	257
0.2-0.3	2221
0.3-0.4	4415
0.4-0.5	1964
0.5-0.6	219
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
0.619	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7623	Phase 3
0.616	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7333	Discontinued
0.6117	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.596	Remote Similarity	NPD815	Approved
0.596	Remote Similarity	NPD816	Approved
0.5878	Remote Similarity	NPD7746	Phase 1
0.5878	Remote Similarity	NPD7747	Phase 1
0.5784	Remote Similarity	NPD8264	Approved
0.5748	Remote Similarity	NPD7641	Discontinued
0.5704	Remote Similarity	NPD7260	Phase 2
0.5704	Remote Similarity	NPD4208	Discontinued
0.5688	Remote Similarity	NPD5363	Approved
0.5673	Remote Similarity	NPD4756	Discovery
0.5669	Remote Similarity	NPD7500	Approved
0.5641	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD5779	Approved
0.5614	Remote Similarity	NPD5778	Approved

Structure

CID316730 OpenBabel06191716132D 32 33 0 0 1 0 0 0 0 0999 V2000 6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 6.5000 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 5.1962 9.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 2 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 -3.4641 3.0000 0.0000 C 0 0 2 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 1.7321 2.0000 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 -0.0000 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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 3 18 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 9 2 0 0 0 0 8 18 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 22 2 0 0 0 0 16 27 1 0 0 0 0 17 2 1 6 0 0 0 19 4 1 6 0 0 0 20 22 1 0 0 0 0 21 28 1 1 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 29 2 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 26 31 2 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	54732917
ChEMBL	CHEMBL1669191
ZINC

Physicochemical Properties

Molecular Weight:	441.25
ALogP:	-0.2715
MLogP:	3.66
XLogP:	5.717
# Rotatable Bonds:	16
Polar Surface Area:	98.07
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	32

Download Data

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General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs