NPASS Natural Product

Natural Product: NPC288629

Natural Product ID:	NPC288629
Common Name:	Ircinal
IUPAC Name:
Synonyms:	Ircinal; Ircinal A
Molecular Formula:	C26H38N2O2
Standard InCHIKey:	VGYIUIBYSYNRNZ-ZDWSRKPSSA-N
Standard InCHI:	InChI=1S/C26H38N2O2/c29-19-21-17-26(30)13-8-4-1-2-5-9-14-27-16-12-23(21)25(20-27)18-22-11-7-3-6-10-15-28(22)24(25)26/h1,4,7,11,17,19,22-24,30H,2-3,5-6,8-10,12-16,18,20H2/b4-1-,11-7-/t22-,23-,24+,25-,26-/m0/s1
Canonical SMILES:	O=CC1=C[C@@]2(O)CC/C=CCCCCN3CC[C@@H]1[C@@]1([C@H]2N2[C@H](C1)C=CCCCC2)C3
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
NPO33280	acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota		Collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia		PMID[16872140]

Biological Activity

Activity Type	# Activity
EC50	2
IC50	4
MIC	1
Others	3

Activity Type	# Activity
Individual Protein	1
Organism	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	Inhibition	=	0	%	10.1016/j.cropro.2012.04.001
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	6800	nM	Open TG-GATES in vivo data: Biochemistry
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	50	ug/ml	16378371
NPT2	Others	Unspecified		IC50	=	330	nM	25871261
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	8.5	ug/ml	10.6019/CHEMBL1201861
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	4.6	ug/ml	10.6019/CHEMBL1201861
NPT2	Others	Unspecified		IC50	>	10000	nM	10579870
NPT2	Others	Unspecified		Activity	=	4.6	nM	18993063
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	30.2	ug/ml	12444691
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	6800	nM	18070975

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 NPC288629 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	72
0.1-0.2	531
0.2-0.3	3938
0.3-0.4	14916
0.4-0.5	9457
0.5-0.6	1909
0.6-0.7	66
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	Natural Product ID
0.6864	Remote Similarity	NPC77703
0.6842	Remote Similarity	NPC470539
0.6692	Remote Similarity	NPC476951
0.6615	Remote Similarity	NPC88190
0.6612	Remote Similarity	NPC474563
0.6589	Remote Similarity	NPC471673
0.6532	Remote Similarity	NPC476276
0.6529	Remote Similarity	NPC226509
0.6529	Remote Similarity	NPC152718
0.6518	Remote Similarity	NPC76283
0.6504	Remote Similarity	NPC476328
0.6475	Remote Similarity	NPC473254
0.6462	Remote Similarity	NPC476952
0.6462	Remote Similarity	NPC96731
0.6444	Remote Similarity	NPC96010
0.6444	Remote Similarity	NPC262880
0.6444	Remote Similarity	NPC247902
0.6444	Remote Similarity	NPC317654
0.6423	Remote Similarity	NPC475239
0.64	Remote Similarity	NPC307903
0.64	Remote Similarity	NPC140251
0.6336	Remote Similarity	NPC470300
0.6328	Remote Similarity	NPC314550
0.6311	Remote Similarity	NPC144714
0.6311	Remote Similarity	NPC100810
0.6304	Remote Similarity	NPC41162
0.629	Remote Similarity	NPC469958
0.627	Remote Similarity	NPC207820
0.6261	Remote Similarity	NPC324506
0.623	Remote Similarity	NPC477964
0.6198	Remote Similarity	NPC476344
0.619	Remote Similarity	NPC46981
0.619	Remote Similarity	NPC271562
0.6186	Remote Similarity	NPC145707
0.6183	Remote Similarity	NPC66007
0.6167	Remote Similarity	NPC150041
0.616	Remote Similarity	NPC133420
0.6159	Remote Similarity	NPC478136
0.6129	Remote Similarity	NPC473289
0.6111	Remote Similarity	NPC472856
0.6111	Remote Similarity	NPC230677
0.6107	Remote Similarity	NPC272166
0.609	Remote Similarity	NPC17581
0.609	Remote Similarity	NPC476155
0.609	Remote Similarity	NPC174463
0.6077	Remote Similarity	NPC124358
0.6066	Remote Similarity	NPC91036
0.6061	Remote Similarity	NPC470538
0.6048	Remote Similarity	NPC474348
0.6047	Remote Similarity	NPC473232
0.6033	Remote Similarity	NPC25033
0.6033	Remote Similarity	NPC471635
0.6033	Remote Similarity	NPC119225
0.6033	Remote Similarity	NPC470382
0.6033	Remote Similarity	NPC476261
0.6032	Remote Similarity	NPC477001
0.6032	Remote Similarity	NPC87919
0.6032	Remote Similarity	NPC477000
0.6	Remote Similarity	NPC475975
0.6	Remote Similarity	NPC247060
0.6	Remote Similarity	NPC11379
0.6	Remote Similarity	NPC230849
0.6	Remote Similarity	NPC471083
0.6	Remote Similarity	NPC50815
0.6	Remote Similarity	NPC476412
0.6	Remote Similarity	NPC13351
0.5969	Remote Similarity	NPC274895
0.5969	Remote Similarity	NPC175585
0.5969	Remote Similarity	NPC470536
0.5957	Remote Similarity	NPC478139
0.5956	Remote Similarity	NPC238323
0.5956	Remote Similarity	NPC315188
0.5948	Remote Similarity	NPC70685
0.5948	Remote Similarity	NPC182106
0.5948	Remote Similarity	NPC311769
0.5944	Remote Similarity	NPC313348
0.5944	Remote Similarity	NPC475987
0.5942	Remote Similarity	NPC97580
0.5938	Remote Similarity	NPC176773
0.5935	Remote Similarity	NPC184033
0.5931	Remote Similarity	NPC45813
0.5929	Remote Similarity	NPC476560
0.5929	Remote Similarity	NPC472301
0.5926	Remote Similarity	NPC470788
0.5926	Remote Similarity	NPC35037
0.5923	Remote Similarity	NPC476290
0.5923	Remote Similarity	NPC63511
0.592	Remote Similarity	NPC188785
0.5917	Remote Similarity	NPC110875
0.5917	Remote Similarity	NPC299808
0.5917	Remote Similarity	NPC118844
0.5917	Remote Similarity	NPC72183
0.5909	Remote Similarity	NPC478137
0.5906	Remote Similarity	NPC212874
0.5897	Remote Similarity	NPC194417
0.5893	Remote Similarity	NPC275494
0.5893	Remote Similarity	NPC475994
0.5893	Remote Similarity	NPC471409
0.5891	Remote Similarity	NPC476918
0.5891	Remote Similarity	NPC470535
0.5887	Remote Similarity	NPC91604
0.5882	Remote Similarity	NPC472983
0.5878	Remote Similarity	NPC470534
0.5873	Remote Similarity	NPC469598
0.5867	Remote Similarity	NPC276822
0.5859	Remote Similarity	NPC55462
0.5859	Remote Similarity	NPC86906
0.5857	Remote Similarity	NPC470537
0.5857	Remote Similarity	NPC280903
0.5854	Remote Similarity	NPC289140
0.5854	Remote Similarity	NPC476903
0.5852	Remote Similarity	NPC235625
0.5852	Remote Similarity	NPC471109
0.5852	Remote Similarity	NPC474006
0.5841	Remote Similarity	NPC19900
0.5833	Remote Similarity	NPC476269
0.5833	Remote Similarity	NPC17143
0.5833	Remote Similarity	NPC475342
0.5833	Remote Similarity	NPC47230
0.5827	Remote Similarity	NPC90538
0.5826	Remote Similarity	NPC224072
0.5821	Remote Similarity	NPC28280
0.5821	Remote Similarity	NPC304646
0.5816	Remote Similarity	NPC471586
0.5812	Remote Similarity	NPC476426
0.5802	Remote Similarity	NPC328052
0.5798	Remote Similarity	NPC259252
0.5789	Remote Similarity	NPC477963
0.5785	Remote Similarity	NPC475806
0.5781	Remote Similarity	NPC119329
0.5781	Remote Similarity	NPC44514
0.5763	Remote Similarity	NPC472974
0.5752	Remote Similarity	NPC473446
0.5752	Remote Similarity	NPC62336
0.5752	Remote Similarity	NPC473695
0.575	Remote Similarity	NPC472973
0.575	Remote Similarity	NPC123912
0.5748	Remote Similarity	NPC476755
0.5743	Remote Similarity	NPC473955
0.5738	Remote Similarity	NPC474736
0.5736	Remote Similarity	NPC195841
0.5736	Remote Similarity	NPC93179
0.5736	Remote Similarity	NPC233256
0.5736	Remote Similarity	NPC476926
0.5725	Remote Similarity	NPC218602
0.5714	Remote Similarity	NPC263582
0.5714	Remote Similarity	NPC19907
0.5714	Remote Similarity	NPC287079
0.5714	Remote Similarity	NPC80834
0.5714	Remote Similarity	NPC469968
0.5703	Remote Similarity	NPC241879
0.5703	Remote Similarity	NPC98765
0.5703	Remote Similarity	NPC265094
0.5702	Remote Similarity	NPC308038
0.5702	Remote Similarity	NPC152061
0.5694	Remote Similarity	NPC261730
0.5694	Remote Similarity	NPC161644
0.5694	Remote Similarity	NPC120335
0.5694	Remote Similarity	NPC472413
0.5691	Remote Similarity	NPC476754
0.5691	Remote Similarity	NPC292793
0.5691	Remote Similarity	NPC299100
0.5691	Remote Similarity	NPC8993
0.569	Remote Similarity	NPC39966
0.569	Remote Similarity	NPC279186
0.569	Remote Similarity	NPC158411
0.569	Remote Similarity	NPC38796
0.5683	Remote Similarity	NPC478138
0.5682	Remote Similarity	NPC469603
0.5674	Remote Similarity	NPC309525
0.5672	Remote Similarity	NPC193471
0.5672	Remote Similarity	NPC130124
0.5669	Remote Similarity	NPC34193
0.5667	Remote Similarity	NPC34754
0.5667	Remote Similarity	NPC472870
0.5662	Remote Similarity	NPC476190
0.5662	Remote Similarity	NPC477121
0.5659	Remote Similarity	NPC476921
0.5656	Remote Similarity	NPC172101
0.5656	Remote Similarity	NPC472978
0.5652	Remote Similarity	NPC471514
0.5652	Remote Similarity	NPC209232
0.5652	Remote Similarity	NPC36495
0.5652	Remote Similarity	NPC45495
0.5649	Remote Similarity	NPC266697
0.5649	Remote Similarity	NPC159367
0.5645	Remote Similarity	NPC259286
0.5645	Remote Similarity	NPC180950
0.5641	Remote Similarity	NPC307258
0.5641	Remote Similarity	NPC97913
0.5639	Remote Similarity	NPC79238
0.5638	Remote Similarity	NPC25025
0.5634	Remote Similarity	NPC475610
0.563	Remote Similarity	NPC472869
0.563	Remote Similarity	NPC166458
0.563	Remote Similarity	NPC322672
0.5625	Remote Similarity	NPC176012
0.5625	Remote Similarity	NPC58200
0.562	Remote Similarity	NPC9714
0.562	Remote Similarity	NPC310236

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC288629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	90
0.1-0.2	318
0.2-0.3	2077
0.3-0.4	4515
0.4-0.5	1898
0.5-0.6	260
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
0.625	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7333	Discontinued
0.6107	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD2132	Phase 3
0.5734	Remote Similarity	NPD6914	Discontinued
0.5643	Remote Similarity	NPD7122	Discontinued
0.563	Remote Similarity	NPD4519	Discontinued
0.563	Remote Similarity	NPD4623	Approved
0.5612	Remote Similarity	NPD7739	Clinical (unspecified phase)

Structure

NPC288629 OpenBabel07101719252D 30 34 0 0 1 0 0 0 0 0999 V2000 -3.3956 -1.3992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7093 -0.8916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3303 0.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8928 -1.7205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7716 -0.2982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3303 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6478 1.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3003 -1.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5704 0.2635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6478 -0.6825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6825 1.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1812 0.5555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7357 -1.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1453 0.6822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6825 -0.6825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2648 0.8604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2706 -1.2810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9180 1.2635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7579 -0.7019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9882 0.8039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8380 -0.5001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4453 0.3817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9180 -0.2983 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4854 0.4826 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3106 -1.1801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5806 0.8751 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -5.3253 0.0790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4039 -1.5110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 27 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 29 2 0 0 0 0 20 25 1 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 22 28 1 6 0 0 0 23 25 1 1 0 0 0 24 25 1 1 0 0 0 24 26 1 0 0 0 0 24 28 1 0 0 0 0 25 18 1 1 0 0 0 26 30 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	5270588
ChEMBL	CHEMBL332054
ZINC

Physicochemical Properties

Molecular Weight:	410.29
ALogP:	-0.6137
MLogP:	3.88
XLogP:	3.264
# Rotatable Bonds:	2
Polar Surface Area:	43.78
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	30

Download Data

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General Info & Identifiers & Properties
Structure MOL file
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