NPASS Natural Product

Natural Product: NPC132662

Natural Product ID:	NPC132662
Common Name:	Lyngbyabellin A
IUPAC Name:
Synonyms:
Molecular Formula:	C29H40Cl2N4O7S2
Standard InCHIKey:	VJSNPXXBMRWPEJ-CEDBRAGKSA-N
Standard InCHI:	InChI=1S/C29H40Cl2N4O7S2/c1-8-15(2)20-23-34-17(14-43-23)25(38)41-18(10-9-11-29(7,30)31)27(3,4)26(39)42-21(28(5,6)40)24-33-16(13-44-24)22(37)32-12-19(36)35-20/h13-15,18,20-21,40H,8-12H2,1-7H3,(H,32,37)(H,35,36)/t15-,18-,20-,21+/m0/s1
Canonical SMILES:	CC[C@@H]([C@@H]1N=C(O)CN=C(O)c2csc(n2)[C@@H](OC(=O)C([C@@H](OC(=O)c2nc1sc2)CCCC(Cl)(Cl)C)(C)C)C(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
NPO26389	Lyngbya majuscula	Species	Oscillatoriaceae	Bacteria				PMID[10843570]

Biological Activity

Activity Type	# Activity
AC50	5
IC50	4
Others	1
Potency	8

Activity Type	# Activity
Cell Line	5
Individual Protein	4
Organism	3
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency		73.1	nM	25278237
NPT1283	Individual Protein	Paired box protein Pax-8	Homo sapiens	AC50	<	260	nM	21044847
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency		15848.9	nM	15730249
NPT2	Others	Unspecified		Potency		51.7	nM	20553004
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	22	nM	25748161
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	AC50	=	2720	nM	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified		Potency		5623.4	nM	18512987
NPT2	Others	Unspecified		Potency		183.6	nM	21882831
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	2.4	mg/kg	11076549
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	AC50	=	2100	nM	10579870
NPT165	Cell Line	HeLa	Homo sapiens	AC50	<	195	nM	21905738
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	47	nM	22037378
NPT2	Others	Unspecified		AC50	=	2160	nM	15043423
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency		2059.6	nM	18494522
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency		25118.9	nM	10869199
NPT2	Others	Unspecified		Potency		6309.6	nM	20695427
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	0.5	ug/ml	PubChem BioAssay data set
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.03	ug/ml	PubChem BioAssay data set

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 NPC132662 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	130
0.1-0.2	1651
0.2-0.3	17337
0.3-0.4	10550
0.4-0.5	1067
0.5-0.6	72
0.6-0.7	72
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC164006
0.925	High Similarity	NPC475554
0.9202	High Similarity	NPC134480
0.9146	High Similarity	NPC473704
0.9119	High Similarity	NPC216720
0.9062	High Similarity	NPC210424
0.7429	Intermediate Similarity	NPC56058
0.7429	Intermediate Similarity	NPC522
0.7205	Intermediate Similarity	NPC89592
0.7176	Intermediate Similarity	NPC475390
0.6959	Remote Similarity	NPC469801
0.6957	Remote Similarity	NPC51692
0.6928	Remote Similarity	NPC74917
0.6886	Remote Similarity	NPC120917
0.6855	Remote Similarity	NPC214375
0.6796	Remote Similarity	NPC237219
0.6748	Remote Similarity	NPC267605
0.6704	Remote Similarity	NPC50274
0.6564	Remote Similarity	NPC135558
0.6532	Remote Similarity	NPC103268
0.6467	Remote Similarity	NPC127775
0.6444	Remote Similarity	NPC119481
0.64	Remote Similarity	NPC165538
0.6398	Remote Similarity	NPC312887
0.6389	Remote Similarity	NPC473398
0.6382	Remote Similarity	NPC122427
0.6369	Remote Similarity	NPC319751
0.6344	Remote Similarity	NPC231110
0.6339	Remote Similarity	NPC154873
0.6316	Remote Similarity	NPC101980
0.6316	Remote Similarity	NPC470146
0.6316	Remote Similarity	NPC97078
0.6316	Remote Similarity	NPC34319
0.6304	Remote Similarity	NPC224609
0.6304	Remote Similarity	NPC268063
0.63	Remote Similarity	NPC329961
0.629	Remote Similarity	NPC474538
0.6284	Remote Similarity	NPC474067
0.6284	Remote Similarity	NPC475737
0.6284	Remote Similarity	NPC474094
0.6284	Remote Similarity	NPC185665
0.625	Remote Similarity	NPC61667
0.625	Remote Similarity	NPC252616
0.625	Remote Similarity	NPC109498
0.625	Remote Similarity	NPC163147
0.625	Remote Similarity	NPC32583
0.625	Remote Similarity	NPC45576
0.625	Remote Similarity	NPC474090
0.6243	Remote Similarity	NPC222391
0.6237	Remote Similarity	NPC21126
0.6233	Remote Similarity	NPC469858
0.623	Remote Similarity	NPC256912
0.6222	Remote Similarity	NPC190329
0.6203	Remote Similarity	NPC52587
0.6188	Remote Similarity	NPC474069
0.6183	Remote Similarity	NPC212214
0.6183	Remote Similarity	NPC202591
0.6175	Remote Similarity	NPC82436
0.6175	Remote Similarity	NPC474103
0.6175	Remote Similarity	NPC474068
0.6175	Remote Similarity	NPC474064
0.6141	Remote Similarity	NPC474102
0.6141	Remote Similarity	NPC475683
0.6141	Remote Similarity	NPC157194
0.6141	Remote Similarity	NPC474079
0.6141	Remote Similarity	NPC474080
0.6141	Remote Similarity	NPC21449
0.6138	Remote Similarity	NPC110129
0.6138	Remote Similarity	NPC201014
0.6122	Remote Similarity	NPC161242
0.6117	Remote Similarity	NPC315252
0.6075	Remote Similarity	NPC474515
0.6075	Remote Similarity	NPC206724
0.6061	Remote Similarity	NPC229160
0.6061	Remote Similarity	NPC263485
0.6061	Remote Similarity	NPC25316
0.6041	Remote Similarity	NPC476080
0.6041	Remote Similarity	NPC475534
0.6028	Remote Similarity	NPC14877
0.6028	Remote Similarity	NPC145178
0.6028	Remote Similarity	NPC475350
0.601	Remote Similarity	NPC475330
0.598	Remote Similarity	NPC174652
0.5979	Remote Similarity	NPC217981
0.5979	Remote Similarity	NPC24990
0.5955	Remote Similarity	NPC474070
0.5949	Remote Similarity	NPC476103
0.5945	Remote Similarity	NPC251036
0.5863	Remote Similarity	NPC313966
0.5863	Remote Similarity	NPC314254
0.5852	Remote Similarity	NPC475196
0.5789	Remote Similarity	NPC239660
0.5789	Remote Similarity	NPC106235
0.5707	Remote Similarity	NPC96016

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC132662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	110
0.1-0.2	595
0.2-0.3	3386
0.3-0.4	4266
0.4-0.5	773
0.5-0.6	25
0.6-0.7	6
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
0.6448	Remote Similarity	NPD6915	Approved
0.6402	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6907	Phase 2
0.6237	Remote Similarity	NPD6910	Phase 3
0.6228	Remote Similarity	NPD9579	Approved
0.615	Remote Similarity	NPD6911	Discontinued
0.5789	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD2957	Phase 2

Structure

NPC132662 OpenBabel07101719252D 44 46 0 0 1 0 0 0 0 0999 V2000 -4.2218 3.7986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3887 4.2898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2265 -1.6383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3521 -1.9352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0155 -0.6056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7699 0.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 -2.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5509 3.1277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9137 -0.8951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9661 -0.8455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -1.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5031 3.1767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1635 1.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8439 1.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6343 3.3733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7390 2.2743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4378 1.2421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5353 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0322 3.1767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9633 2.7023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4280 0.3110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4280 2.7023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2743 2.2743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7390 0.7390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2743 0.7390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5031 -0.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0322 -0.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0990 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2921 -1.7903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2424 -2.7378 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.8089 -0.9944 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2967 1.5066 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4378 1.7712 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5353 3.0133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1806 4.1140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0990 3.3733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1198 0.3082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3547 -1.1007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 -1.2766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9633 0.3110 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 -2.7621 2.0870 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.1635 1.0322 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 11 29 1 0 0 0 0 12 19 1 0 0 0 0 12 32 1 0 0 0 0 13 16 2 0 0 0 0 13 44 1 0 0 0 0 14 17 2 0 0 0 0 14 43 1 0 0 0 0 15 2 1 6 0 0 0 16 22 1 0 0 0 0 16 33 1 0 0 0 0 17 25 1 0 0 0 0 17 34 1 0 0 0 0 18 10 1 6 0 0 0 18 27 1 0 0 0 0 18 41 1 0 0 0 0 19 35 2 3 0 0 0 19 36 1 0 0 0 0 20 15 1 6 0 0 0 20 23 1 0 0 0 0 20 35 1 0 0 0 0 21 24 1 0 0 0 0 21 28 1 6 0 0 0 21 42 1 0 0 0 0 22 32 2 3 0 0 0 22 37 1 0 0 0 0 23 34 2 0 0 0 0 23 43 1 0 0 0 0 24 33 2 0 0 0 0 24 44 1 0 0 0 0 25 38 2 0 0 0 0 25 41 1 0 0 0 0 26 27 1 0 0 0 0 26 39 2 0 0 0 0 26 42 1 0 0 0 0 28 40 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10032587
ChEMBL	CHEMBL453207
ZINC

Physicochemical Properties

Molecular Weight:	690.17
ALogP:	1.5901
MLogP:	3
XLogP:	5.196
# Rotatable Bonds:	19
Polar Surface Area:	220.27
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	44

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General Info & Identifiers & Properties
Structure MOL file
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