NPASS Natural Product

Natural Product: NPC300912

Natural Product ID:	NPC300912
Common Name:	Aplysinone A
IUPAC Name:	(5S,6R)-7,9-dibromo-N-[5-[[(5S,6R,7S)-7,9-dibromo-6-hydroxy-8-oxo-1-oxa-2-azaspiro[4.5]deca-2,9-diene-3-carbonyl]amino]pentyl]-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:
Molecular Formula:	C24H26Br4N4O8
Standard InCHIKey:	KCVKPVRAUSPLPZ-CPXJRIKISA-N
Standard InCHI:	InChI=1S/C24H26Br4N4O8/c1-38-18-12(26)8-24(20(35)16(18)28)10-14(32-40-24)22(37)30-6-4-2-3-5-29-21(36)13-9-23(39-31-13)7-11(25)17(33)15(27)19(23)34/h7-8,15,19-20,34-35H,2-6,9-10H2,1H3,(H,29,36)(H,30,37)/t15-,19+,20+,23-,24-/m1/s1
Canonical SMILES:	COC1=C(Br)[C@@H]([C@]2(C=C1Br)ON=C(C2)C(=O)NCCCCCNC(=O)C1=NO[C@@]2(C1)C=C(Br)C(=O)[C@H]([C@@H]2O)Br)O
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
NPO8996	Aplysina gerardogreeni	Species	Aplysinidae	Eukaryota				PMID[17512741]

Biological Activity

Activity Type	# Activity
GI50	3
Others	6

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	9100	nM	20934335
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	4800	nM	8350085
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	2800	nM	10514307
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	8200	nM	10514307
NPT81	Cell Line	A549	Homo sapiens	GI50	=	4500	nM	10514307
NPT81	Cell Line	A549	Homo sapiens	TGI	=	7100	nM	10514307
NPT81	Cell Line	A549	Homo sapiens	LC50	>	10	ug/ml	18479163
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	3300	nM	18479163
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	5400	nM	18479163

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 NPC300912 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	94
0.1-0.2	656
0.2-0.3	5002
0.3-0.4	20043
0.4-0.5	4823
0.5-0.6	242
0.6-0.7	10
0.7-0.8	4
0.8-0.85	4
0.85-0.9	3
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473262
1.0	High Similarity	NPC202166
1.0	High Similarity	NPC473261
0.9302	High Similarity	NPC172626
0.9302	High Similarity	NPC470892
0.913	High Similarity	NPC130714
0.907	High Similarity	NPC158672
0.907	High Similarity	NPC1702
0.8905	High Similarity	NPC470886
0.8864	High Similarity	NPC477220
0.854	High Similarity	NPC473683
0.8209	Intermediate Similarity	NPC313173
0.8195	Intermediate Similarity	NPC66855
0.8088	Intermediate Similarity	NPC260270
0.8015	Intermediate Similarity	NPC145149
0.7972	Intermediate Similarity	NPC289324
0.7958	Intermediate Similarity	NPC181086
0.7847	Intermediate Similarity	NPC81079
0.7832	Intermediate Similarity	NPC304257
0.663	Remote Similarity	NPC202866
0.6333	Remote Similarity	NPC77435
0.6333	Remote Similarity	NPC259071
0.6324	Remote Similarity	NPC45830
0.6324	Remote Similarity	NPC243106
0.6298	Remote Similarity	NPC174607
0.6264	Remote Similarity	NPC147847
0.6129	Remote Similarity	NPC227953
0.6014	Remote Similarity	NPC133729
0.6013	Remote Similarity	NPC473249
0.5938	Remote Similarity	NPC123140
0.5887	Remote Similarity	NPC68001
0.5887	Remote Similarity	NPC199831
0.5887	Remote Similarity	NPC474827
0.5887	Remote Similarity	NPC474828
0.5828	Remote Similarity	NPC477143
0.5828	Remote Similarity	NPC477140
0.5823	Remote Similarity	NPC314361
0.582	Remote Similarity	NPC201900
0.5808	Remote Similarity	NPC470746
0.5808	Remote Similarity	NPC471336
0.5806	Remote Similarity	NPC475610
0.5806	Remote Similarity	NPC8093
0.5806	Remote Similarity	NPC121571
0.5767	Remote Similarity	NPC315210
0.5767	Remote Similarity	NPC315848
0.5764	Remote Similarity	NPC251330
0.5753	Remote Similarity	NPC469603
0.5745	Remote Similarity	NPC313234
0.5733	Remote Similarity	NPC476190
0.5724	Remote Similarity	NPC474099
0.5707	Remote Similarity	NPC471338
0.5707	Remote Similarity	NPC474678
0.5686	Remote Similarity	NPC315915
0.5677	Remote Similarity	NPC36254
0.5677	Remote Similarity	NPC475843
0.5676	Remote Similarity	NPC314550
0.565	Remote Similarity	NPC471339
0.5629	Remote Similarity	NPC271621
0.5629	Remote Similarity	NPC59751
0.5629	Remote Similarity	NPC27413
0.5616	Remote Similarity	NPC307903
0.5616	Remote Similarity	NPC140251
0.5612	Remote Similarity	NPC471337

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC300912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	94
0.1-0.2	349
0.2-0.3	2603
0.3-0.4	5144
0.4-0.5	937
0.5-0.6	30
0.6-0.7	4
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
0.6067	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7623	Phase 3
0.6013	Remote Similarity	NPD7746	Phase 1
0.6013	Remote Similarity	NPD7747	Phase 1
0.5828	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5608	Remote Similarity	NPD7116	Clinical (unspecified phase)

Structure

NPC300912 OpenBabel07101718272D 40 43 0 0 1 0 0 0 0 0999 V2000 -3.5116 -2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5887 3.9317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9955 3.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5942 4.0362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9900 2.9136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0064 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0617 0.5021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9572 2.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9278 0.0021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9790 2.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7938 1.5021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7938 0.5021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9278 2.0021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 0.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5723 3.6181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0617 1.5021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9278 -0.9979 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -2.0933 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -9.6598 2.0021 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.9067 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.5778 3.7226 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0119 3.3317 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4790 1.8385 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.6598 0.0021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9278 3.0021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1601 4.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 2.6272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1482 1.0954 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 38 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 11 2 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 10 24 1 0 0 0 0 11 17 1 0 0 0 0 11 25 1 0 0 0 0 12 18 1 0 0 0 0 12 26 1 0 0 0 0 13 21 1 0 0 0 0 13 31 2 0 0 0 0 14 22 1 0 0 0 0 14 32 2 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 15 27 1 1 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 33 2 0 0 0 0 18 38 1 0 0 0 0 19 23 1 6 0 0 0 19 34 1 0 0 0 0 20 24 1 6 0 0 0 20 35 1 0 0 0 0 21 29 1 0 0 0 0 21 36 2 0 0 0 0 22 30 1 0 0 0 0 22 37 2 0 0 0 0 23 7 1 6 0 0 0 23 39 1 0 0 0 0 24 8 1 6 0 0 0 24 40 1 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44424473
ChEMBL	CHEMBL274349
ZINC

Physicochemical Properties

Molecular Weight:	813.85
ALogP:	-1.4206
MLogP:	2.34
XLogP:	2.125
# Rotatable Bonds:	18
Polar Surface Area:	168.14
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	40

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