NPASS Natural Product

Natural Product: NPC130714

Natural Product ID:	NPC130714
Common Name:	Aplysinone C
IUPAC Name:	(1'R,5S,6'S)-3'-bromo-N-[5-[[(5S,6R)-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carbonyl]amino]pentyl]-2'-oxospiro[4H-1,2-oxazole-5,5'-7-oxabicyclo[4.1.0]hept-3-ene]-3-carboxamide
Synonyms:	Aplysinone C
Molecular Formula:	C24H25Br3N4O8
Standard InCHIKey:	GSUVKSRKZPOPBP-DRRHGHKVSA-N
Standard InCHI:	InChI=1S/C24H25Br3N4O8/c1-36-17-12(26)8-23(19(33)15(17)27)9-13(30-38-23)21(34)28-5-3-2-4-6-29-22(35)14-10-24(39-31-14)7-11(25)16(32)18-20(24)37-18/h7-8,18-20,33H,2-6,9-10H2,1H3,(H,28,34)(H,29,35)/t18-,19-,20-,23+,24+/m0/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]1[C@@H]2O1)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	>	10	ug/ml	17958396
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	5800	nM	17958396
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	6400	nM	17958396
NPT139	Cell Line	HT-29	Homo sapiens	TGI	>	10	ug/ml	17958396
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	5600	nM	17958396
NPT81	Cell Line	A549	Homo sapiens	LC50	>	10	ug/ml	17958396
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	12600	nM	17958396
NPT81	Cell Line	A549	Homo sapiens	GI50	=	10700	nM	17958396
NPT81	Cell Line	A549	Homo sapiens	TGI	>	10	ug/ml	17958396

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 NPC130714 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	99
0.1-0.2	719
0.2-0.3	4137
0.3-0.4	19016
0.4-0.5	6450
0.5-0.6	436
0.6-0.7	13
0.7-0.8	8
0.8-0.85	5
0.85-0.9	2
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC473261
0.913	High Similarity	NPC202166
0.913	High Similarity	NPC473262
0.913	High Similarity	NPC300912
0.8529	High Similarity	NPC1702
0.8529	High Similarity	NPC158672
0.8478	Intermediate Similarity	NPC172626
0.8478	Intermediate Similarity	NPC470892
0.8403	Intermediate Similarity	NPC470886
0.8345	Intermediate Similarity	NPC477220
0.8056	Intermediate Similarity	NPC473683
0.7857	Intermediate Similarity	NPC313173
0.7842	Intermediate Similarity	NPC66855
0.7746	Intermediate Similarity	NPC260270
0.7676	Intermediate Similarity	NPC145149
0.7635	Intermediate Similarity	NPC181086
0.7533	Intermediate Similarity	NPC81079
0.7517	Intermediate Similarity	NPC304257
0.7417	Intermediate Similarity	NPC289324
0.6417	Remote Similarity	NPC202866
0.6135	Remote Similarity	NPC315848
0.6135	Remote Similarity	NPC315210
0.6129	Remote Similarity	NPC259071
0.6129	Remote Similarity	NPC77435
0.6096	Remote Similarity	NPC174607
0.6065	Remote Similarity	NPC469494
0.6064	Remote Similarity	NPC147847
0.6056	Remote Similarity	NPC45830
0.6056	Remote Similarity	NPC243106
0.6014	Remote Similarity	NPC170375
0.6013	Remote Similarity	NPC473808
0.6	Remote Similarity	NPC314361
0.5987	Remote Similarity	NPC473249
0.5974	Remote Similarity	NPC315915
0.5938	Remote Similarity	NPC227953
0.5921	Remote Similarity	NPC27413
0.5921	Remote Similarity	NPC59751
0.5921	Remote Similarity	NPC271621
0.5909	Remote Similarity	NPC477140
0.5909	Remote Similarity	NPC477143
0.5882	Remote Similarity	NPC296361
0.5878	Remote Similarity	NPC133729
0.5871	Remote Similarity	NPC469515
0.5862	Remote Similarity	NPC474828
0.5862	Remote Similarity	NPC199831
0.5862	Remote Similarity	NPC68001
0.5862	Remote Similarity	NPC474827
0.586	Remote Similarity	NPC36254
0.5855	Remote Similarity	NPC315652
0.5855	Remote Similarity	NPC7905
0.5839	Remote Similarity	NPC469603
0.5838	Remote Similarity	NPC123140
0.5828	Remote Similarity	NPC5485
0.5793	Remote Similarity	NPC128501
0.5782	Remote Similarity	NPC469852
0.5772	Remote Similarity	NPC24389
0.5743	Remote Similarity	NPC251330
0.5724	Remote Similarity	NPC313234
0.5714	Remote Similarity	NPC470746
0.5714	Remote Similarity	NPC471336
0.5714	Remote Similarity	NPC476190
0.5707	Remote Similarity	NPC8093
0.5707	Remote Similarity	NPC121571
0.5705	Remote Similarity	NPC474099
0.5696	Remote Similarity	NPC280498
0.5687	Remote Similarity	NPC475610
0.5676	Remote Similarity	NPC271269
0.5669	Remote Similarity	NPC156379
0.5669	Remote Similarity	NPC475383
0.5657	Remote Similarity	NPC185404
0.5641	Remote Similarity	NPC201900
0.5612	Remote Similarity	NPC471338
0.5612	Remote Similarity	NPC474678

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC130714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	395
0.2-0.3	2620
0.3-0.4	4819
0.4-0.5	1170
0.5-0.6	55
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
0.6118	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD7623	Phase 3
0.6039	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD7746	Phase 1
0.5987	Remote Similarity	NPD7747	Phase 1
0.5823	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8273	Phase 1

Structure

NPC130714 OpenBabel07101718292D 39 43 0 0 1 0 0 0 0 0999 V2000 2.6366 -3.1887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5594 2.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5540 2.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1527 1.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1417 2.1318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1582 1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2346 -1.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3392 0.3059 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 -2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3686 -2.1887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3173 0.5138 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 3.5026 -0.6887 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 3.5026 -1.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3686 -0.1887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7240 1.4273 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 5.2346 -0.6887 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 -3.5116 0.9067 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.3686 -3.1887 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.6366 -0.1887 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.1363 2.2363 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 6.8173 -0.3522 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 -3.5116 -1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3686 0.8113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7186 1.5319 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 2.6366 -2.1887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -1.5933 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 36 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 28 1 0 0 0 0 6 29 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 16 1 0 0 0 0 11 25 1 0 0 0 0 12 17 1 0 0 0 0 12 26 1 0 0 0 0 13 21 1 0 0 0 0 13 30 2 0 0 0 0 14 22 1 0 0 0 0 14 31 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 15 27 1 0 0 0 0 16 32 2 0 0 0 0 17 36 1 0 0 0 0 18 16 1 1 0 0 0 18 20 1 0 0 0 0 18 37 1 0 0 0 0 19 23 1 6 0 0 0 19 33 1 0 0 0 0 20 24 1 1 0 0 0 20 37 1 0 0 0 0 21 28 1 0 0 0 0 21 34 2 0 0 0 0 22 29 1 0 0 0 0 22 35 2 0 0 0 0 23 8 1 6 0 0 0 23 38 1 0 0 0 0 24 7 1 6 0 0 0 24 39 1 0 0 0 0 30 38 1 0 0 0 0 31 39 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44424474
ChEMBL	CHEMBL229729
ZINC

Physicochemical Properties

Molecular Weight:	733.92
ALogP:	-2.0032
MLogP:	2.45
XLogP:	1.764
# Rotatable Bonds:	16
Polar Surface Area:	160.44
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	39

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