NPASS Natural Product

Natural Product: NPC81195

Natural Product ID:	NPC81195
Common Name:	Malyngamide O
IUPAC Name:	methyl (2E,5Z)-6-chloro-3-methoxy-5-[[[(E,7S)-7-methoxytetradec-4-enoyl]-methylamino]methyl]hexa-2,5-dienoate
Synonyms:	Malyngamide O
Molecular Formula:	C25H42ClNO5
Standard InCHIKey:	APYMXRPHYRRJTM-ZWUHNMOSSA-N
Standard InCHI:	InChI=1S/C25H42ClNO5/c1-6-7-8-9-11-14-22(30-3)15-12-10-13-16-24(28)27(2)20-21(19-26)17-23(31-4)18-25(29)32-5/h10,12,18-19,22H,6-9,11,13-17,20H2,1-5H3/b12-10+,21-19-,23-18+/t22-/m0/s1
Canonical SMILES:	CCCCCCC[C@@H](C/C=C/CCC(=O)N(C/C(=CCl)/C/C(=CC(=O)OC)/OC)C)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO13233	Solanum megacarpum	Species	Solanaceae	Eukaryota	UNPD*
NPO16759	Polyalthia debilis	Species	Annonaceae	Eukaryota	UNPD*
NPO15140	Soja max	Species	Fabaceae	Eukaryota	UNPD*
NPO21487	Eunicea flexuosa	Species	Plexauridae	Eukaryota	UNPD*
NPO11600	Scolopendra subspinipes	Species	Scolopendridae	Eukaryota	UNPD*
NPO3396	Allium cernuum	Species	Amaryllidaceae	Eukaryota	UNPD*
NPO12135	Rhamnus triquetra	Species	Rhamnaceae	Eukaryota	UNPD*
NPO16176	Citrus fusca	Species	Rutaceae	Eukaryota	UNPD*
NPO12302	Hebanthe paniculata	Species	Amaranthaceae	Eukaryota	UNPD*

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	2	ug/ml	11076568
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2	ug/ml	11076568
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2	ug/ml	11076568

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 NPC81195 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	388
0.2-0.3	4591
0.3-0.4	17638
0.4-0.5	6675
0.5-0.6	1502
0.6-0.7	48
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8352	Intermediate Similarity	NPC53240
0.75	Intermediate Similarity	NPC233932
0.7264	Intermediate Similarity	NPC21324
0.7129	Intermediate Similarity	NPC52820
0.6952	Remote Similarity	NPC474828
0.6952	Remote Similarity	NPC474827
0.6952	Remote Similarity	NPC199831
0.6952	Remote Similarity	NPC68001
0.6882	Remote Similarity	NPC477523
0.6857	Remote Similarity	NPC474244
0.6809	Remote Similarity	NPC477524
0.6774	Remote Similarity	NPC471768
0.6697	Remote Similarity	NPC474099
0.6535	Remote Similarity	NPC159568
0.6476	Remote Similarity	NPC476344
0.6465	Remote Similarity	NPC130436
0.6465	Remote Similarity	NPC469860
0.6465	Remote Similarity	NPC469861
0.6458	Remote Similarity	NPC226982
0.6458	Remote Similarity	NPC277341
0.6442	Remote Similarity	NPC150041
0.6422	Remote Similarity	NPC469604
0.6372	Remote Similarity	NPC58281
0.6364	Remote Similarity	NPC296589
0.6355	Remote Similarity	NPC474985
0.6354	Remote Similarity	NPC209232
0.6321	Remote Similarity	NPC241426
0.6304	Remote Similarity	NPC474705
0.6283	Remote Similarity	NPC469603
0.6264	Remote Similarity	NPC469660
0.6226	Remote Similarity	NPC175614
0.6222	Remote Similarity	NPC218477
0.6214	Remote Similarity	NPC17143
0.6214	Remote Similarity	NPC47230
0.6211	Remote Similarity	NPC46268
0.6204	Remote Similarity	NPC26597
0.6196	Remote Similarity	NPC84038
0.618	Remote Similarity	NPC248125
0.617	Remote Similarity	NPC34672
0.6168	Remote Similarity	NPC150967
0.6168	Remote Similarity	NPC265662
0.6147	Remote Similarity	NPC77703
0.6126	Remote Similarity	NPC205176
0.6106	Remote Similarity	NPC470072
0.6082	Remote Similarity	NPC473947
0.6068	Remote Similarity	NPC474984
0.6055	Remote Similarity	NPC316730
0.6042	Remote Similarity	NPC325936
0.6	Remote Similarity	NPC469414
0.6	Remote Similarity	NPC329826
0.6	Remote Similarity	NPC188785
0.6	Remote Similarity	NPC284447
0.5978	Remote Similarity	NPC475004
0.5977	Remote Similarity	NPC45097
0.5955	Remote Similarity	NPC477456
0.5955	Remote Similarity	NPC477457
0.5948	Remote Similarity	NPC475608
0.5948	Remote Similarity	NPC21713
0.5941	Remote Similarity	NPC475975
0.5934	Remote Similarity	NPC472266
0.5934	Remote Similarity	NPC203335
0.5932	Remote Similarity	NPC472536
0.5932	Remote Similarity	NPC103391
0.5914	Remote Similarity	NPC97614
0.59	Remote Similarity	NPC123908
0.59	Remote Similarity	NPC10080
0.59	Remote Similarity	NPC473810
0.5897	Remote Similarity	NPC474995
0.5895	Remote Similarity	NPC140287
0.5895	Remote Similarity	NPC476355
0.5895	Remote Similarity	NPC470994
0.5889	Remote Similarity	NPC182794
0.5876	Remote Similarity	NPC471225
0.587	Remote Similarity	NPC96272
0.587	Remote Similarity	NPC474823
0.587	Remote Similarity	NPC475760
0.5862	Remote Similarity	NPC159650
0.5862	Remote Similarity	NPC474267
0.5862	Remote Similarity	NPC22897
0.5859	Remote Similarity	NPC120335
0.5851	Remote Similarity	NPC186531
0.5843	Remote Similarity	NPC179087
0.5843	Remote Similarity	NPC210303
0.5843	Remote Similarity	NPC44343
0.5841	Remote Similarity	NPC470073
0.5841	Remote Similarity	NPC133420
0.5841	Remote Similarity	NPC75523
0.5833	Remote Similarity	NPC260396
0.5833	Remote Similarity	NPC477421
0.5806	Remote Similarity	NPC101622
0.58	Remote Similarity	NPC471325
0.58	Remote Similarity	NPC112868
0.5795	Remote Similarity	NPC79756
0.5789	Remote Similarity	NPC329890
0.5789	Remote Similarity	NPC252503
0.5789	Remote Similarity	NPC185186
0.5789	Remote Similarity	NPC329914
0.5789	Remote Similarity	NPC327383
0.5789	Remote Similarity	NPC154601
0.5789	Remote Similarity	NPC271269
0.5778	Remote Similarity	NPC206660
0.5773	Remote Similarity	NPC123360
0.5769	Remote Similarity	NPC478144
0.5761	Remote Similarity	NPC194871
0.576	Remote Similarity	NPC321197
0.5758	Remote Similarity	NPC477088
0.5752	Remote Similarity	NPC318544
0.5747	Remote Similarity	NPC23418
0.5745	Remote Similarity	NPC64234
0.5745	Remote Similarity	NPC323677
0.5745	Remote Similarity	NPC477429
0.5745	Remote Similarity	NPC4299
0.5745	Remote Similarity	NPC37929
0.5743	Remote Similarity	NPC35556
0.5739	Remote Similarity	NPC251330
0.5736	Remote Similarity	NPC213969
0.5736	Remote Similarity	NPC165726
0.5736	Remote Similarity	NPC17374
0.573	Remote Similarity	NPC270412
0.573	Remote Similarity	NPC252684
0.573	Remote Similarity	NPC14437
0.573	Remote Similarity	NPC151648
0.5729	Remote Similarity	NPC474758
0.5729	Remote Similarity	NPC477204
0.5729	Remote Similarity	NPC227396
0.5728	Remote Similarity	NPC2640
0.5728	Remote Similarity	NPC319913
0.5728	Remote Similarity	NPC475614
0.5726	Remote Similarity	NPC63511
0.5714	Remote Similarity	NPC469597
0.5714	Remote Similarity	NPC329401
0.5714	Remote Similarity	NPC315394
0.5714	Remote Similarity	NPC477987
0.5714	Remote Similarity	NPC475711
0.5714	Remote Similarity	NPC97516
0.5702	Remote Similarity	NPC475642
0.5702	Remote Similarity	NPC477000
0.5702	Remote Similarity	NPC477001
0.5702	Remote Similarity	NPC477553
0.5701	Remote Similarity	NPC472264
0.5699	Remote Similarity	NPC470256
0.5699	Remote Similarity	NPC276290
0.5691	Remote Similarity	NPC477140
0.5691	Remote Similarity	NPC477143
0.5686	Remote Similarity	NPC178758
0.5686	Remote Similarity	NPC253801
0.5686	Remote Similarity	NPC196102
0.5684	Remote Similarity	NPC163003
0.5684	Remote Similarity	NPC475762
0.5684	Remote Similarity	NPC477084
0.5682	Remote Similarity	NPC286189
0.5678	Remote Similarity	NPC474411
0.5678	Remote Similarity	NPC474431
0.5676	Remote Similarity	NPC270813
0.5673	Remote Similarity	NPC69082
0.5673	Remote Similarity	NPC279267
0.5673	Remote Similarity	NPC186332
0.5673	Remote Similarity	NPC47220
0.5673	Remote Similarity	NPC322672
0.567	Remote Similarity	NPC285840
0.567	Remote Similarity	NPC327041
0.567	Remote Similarity	NPC244166
0.5667	Remote Similarity	NPC217940
0.5664	Remote Similarity	NPC473289
0.5657	Remote Similarity	NPC473471
0.5657	Remote Similarity	NPC93763
0.5657	Remote Similarity	NPC128276
0.5657	Remote Similarity	NPC108816
0.5657	Remote Similarity	NPC182292
0.5656	Remote Similarity	NPC477555
0.5652	Remote Similarity	NPC93179
0.5648	Remote Similarity	NPC304897
0.5647	Remote Similarity	NPC478120
0.5641	Remote Similarity	NPC470536
0.5638	Remote Similarity	NPC232812
0.5638	Remote Similarity	NPC477688
0.5638	Remote Similarity	NPC265574
0.5638	Remote Similarity	NPC236208
0.5638	Remote Similarity	NPC151481
0.5635	Remote Similarity	NPC469999
0.5631	Remote Similarity	NPC41856
0.5625	Remote Similarity	NPC477964
0.5625	Remote Similarity	NPC222244
0.5625	Remote Similarity	NPC144419
0.5625	Remote Similarity	NPC477085
0.5625	Remote Similarity	NPC16349
0.5625	Remote Similarity	NPC326126
0.5619	Remote Similarity	NPC478145
0.5619	Remote Similarity	NPC473525
0.5618	Remote Similarity	NPC26223
0.5618	Remote Similarity	NPC158368
0.5618	Remote Similarity	NPC143857
0.5618	Remote Similarity	NPC299730
0.5618	Remote Similarity	NPC154908
0.5618	Remote Similarity	NPC226872
0.5618	Remote Similarity	NPC252851
0.5618	Remote Similarity	NPC229252
0.5614	Remote Similarity	NPC6271
0.5612	Remote Similarity	NPC469880
0.5612	Remote Similarity	NPC477202

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC81195 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	367
0.2-0.3	3098
0.3-0.4	4285
0.4-0.5	1261
0.5-0.6	83
0.6-0.7	2
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
0.6522	Remote Similarity	NPD1452	Discontinued
0.6279	Remote Similarity	NPD3205	Discontinued
0.573	Remote Similarity	NPD9418	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1376	Discontinued
0.5691	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5349	Clinical (unspecified phase)

Structure

CID81195 OpenBabel06191715422D 32 31 0 0 1 0 0 0 0 0999 V2000 12.1244 -4.0000 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 6.0622 -4.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -1.7321 0.0000 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 -0.0000 -3.0000 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 6.9282 -3.0000 0.0000 C 0 0 1 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 -3.0000 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 -1.7321 -4.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 27 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 21 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 22 14 1 6 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 27 1 0 0 0 0 24 28 2 0 0 0 0 25 29 2 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10027764
ChEMBL	CHEMBL485986
ZINC

Physicochemical Properties

Molecular Weight:	471.28
ALogP:	-0.5244
MLogP:	3.44
XLogP:	5.491
# Rotatable Bonds:	26
Polar Surface Area:	65.07
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	32

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Structure MOL file
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