NPASS Natural Product

Natural Product: NPC260270

Natural Product ID:	NPC260270
Common Name:	Aplysinamisine Ii
IUPAC Name:	(5S,6R)-7,9-dibromo-N-[5-(diaminomethylideneamino)pentyl]-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:	Aplysinamisine II
Molecular Formula:	C16H23Br2N5O4
Standard InCHIKey:	GCYSDIFCRYTRFB-XJKSGUPXSA-N
Standard InCHI:	InChI=1S/C16H23Br2N5O4/c1-26-12-9(17)7-16(13(24)11(12)18)8-10(23-27-16)14(25)21-5-3-2-4-6-22-15(19)20/h7,13,24H,2-6,8H2,1H3,(H,21,25)(H4,19,20,22)/t13-,16+/m0/s1
Canonical SMILES:	COC1=C(Br)[C@@H]([C@]2(C=C1Br)ON=C(C2)C(=O)NCCCCCNC(=N)N)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Collection Location	Reference
NPO13261	Suberea clavata	Species	Aplysinellidae	Eukaryota	Australia	PMID[19379003]
NPO11745	Subergorgia suberosa	Species	Subergorgiidae	Eukaryota		UNPD*
NPO11870	Rhododendron arboreum	Species	Ericaceae	Eukaryota		UNPD*
NPO12594	Hybanthus enneaspermus	Species	Violaceae	Eukaryota		UNPD*

Biological Activity

Activity Type	# Activity
GI50	57
IC50	3
Others	2

Activity Type	# Activity
Cell Line	60
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50	ug/ml	8350091
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	50	ug/ml	8350091
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10	ug/ml	8350091
NPT4197	Individual Protein	Coagulation factor XI	Homo sapiens	Inhibition	=	30	%	19379003
NPT4655	Individual Protein	Coagulation factor IX	Homo sapiens	Inhibition	<	5	%	19379003
NPT367	Cell Line	MDA-N	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT368	Cell Line	SN12C	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT369	Cell Line	ACHN	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT371	Cell Line	UO-31	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT374	Cell Line	SF-539	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT376	Cell Line	A498	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT379	Cell Line	HOP-62	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT380	Cell Line	U-251	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT383	Cell Line	SNB-19	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT385	Cell Line	SR	Homo sapiens	GI50		6870.68	nM	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT384	Cell Line	TK-10	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT323	Cell Line	SW-620	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT386	Cell Line	KM12	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT387	Cell Line	M14	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT457	Cell Line	BT-549	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT392	Cell Line	SNB-75	Homo sapiens	GI50		6792.04	nM	PubChem BioAssay data set
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT395	Cell Line	SF-268	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT393	Cell Line	HCT-116	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT83	Cell Line	MCF7	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT396	Cell Line	T47D	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT398	Cell Line	UACC-62	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT399	Cell Line	SF-295	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT401	Cell Line	786-0	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT403	Cell Line	UACC-257	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT406	Cell Line	RXF 393	Homo sapiens	GI50		10000	nM	PubChem BioAssay data set
NPT407	Cell Line	COLO 205	Homo sapiens	GI50		10000	nM	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 NPC260270 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	77
0.1-0.2	559
0.2-0.3	7612
0.3-0.4	19920
0.4-0.5	2498
0.5-0.6	195
0.6-0.7	7
0.7-0.8	7
0.8-0.85	5
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9915	High Similarity	NPC145149
0.9286	High Similarity	NPC181086
0.9141	High Similarity	NPC81079
0.9134	High Similarity	NPC304257
0.9008	High Similarity	NPC66855
0.8871	High Similarity	NPC1702
0.8871	High Similarity	NPC158672
0.8862	High Similarity	NPC313173
0.8661	High Similarity	NPC477220
0.8088	Intermediate Similarity	NPC202166
0.8088	Intermediate Similarity	NPC473262
0.8088	Intermediate Similarity	NPC300912
0.8088	Intermediate Similarity	NPC473261
0.8029	Intermediate Similarity	NPC470886
0.7746	Intermediate Similarity	NPC130714
0.7664	Intermediate Similarity	NPC473683
0.7626	Intermediate Similarity	NPC289324
0.7426	Intermediate Similarity	NPC470892
0.7426	Intermediate Similarity	NPC172626
0.7213	Intermediate Similarity	NPC45830
0.7213	Intermediate Similarity	NPC243106
0.6784	Remote Similarity	NPC201900
0.6301	Remote Similarity	NPC77435
0.6301	Remote Similarity	NPC259071
0.6264	Remote Similarity	NPC174607
0.6229	Remote Similarity	NPC147847
0.6145	Remote Similarity	NPC202866
0.6089	Remote Similarity	NPC227953
0.5915	Remote Similarity	NPC471261
0.587	Remote Similarity	NPC147238
0.5855	Remote Similarity	NPC477400
0.5819	Remote Similarity	NPC477254
0.5796	Remote Similarity	NPC142761
0.5789	Remote Similarity	NPC471256
0.5735	Remote Similarity	NPC471259
0.5714	Remote Similarity	NPC314550
0.5714	Remote Similarity	NPC36254
0.5705	Remote Similarity	NPC315210
0.5705	Remote Similarity	NPC315848
0.5683	Remote Similarity	NPC251122
0.5672	Remote Similarity	NPC313234
0.5669	Remote Similarity	NPC477399
0.5669	Remote Similarity	NPC477401
0.5667	Remote Similarity	NPC121571
0.5667	Remote Similarity	NPC8093
0.5638	Remote Similarity	NPC475610
0.5638	Remote Similarity	NPC473249
0.5616	Remote Similarity	NPC314293
0.5606	Remote Similarity	NPC471257
0.5603	Remote Similarity	NPC478024

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC260270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	80
0.1-0.2	243
0.2-0.3	2287
0.3-0.4	5570
0.4-0.5	945
0.5-0.6	36
0.6-0.7	0
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
0.5782	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD7623	Phase 3
0.5685	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7747	Phase 1
0.5638	Remote Similarity	NPD7746	Phase 1

Structure

CID260270 OpenBabel06191716062D 27 28 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 -3.3784 -4.5589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9716 -3.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3729 -4.6634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9771 -3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7796 -5.5769 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 0.8090 -1.4013 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 -0.1691 -1.6092 0.0000 C 0 0 0 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 2.6456 0.5933 0.0000 C 0 0 0 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 -0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1809 -6.5950 0.0000 C 0 0 0 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 1.7796 2.0933 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 -7.1754 -6.6995 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5931 -7.4040 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5704 -2.6272 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7742 -5.6815 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 1.7796 -1.9067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0119 -3.3317 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 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 21 1 0 0 0 0 6 22 1 0 0 0 0 7 9 2 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 23 2 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 6 0 0 0 13 24 1 0 0 0 0 14 21 1 0 0 0 0 14 25 2 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 7 1 6 0 0 0 16 27 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	6712295
ChEMBL	CHEMBL458691
ZINC

Physicochemical Properties

Molecular Weight:	507.01
ALogP:	-1.6232
MLogP:	2.01
XLogP:	1.765
# Rotatable Bonds:	15
Polar Surface Area:	142.05
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	27

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