NPASS Natural Product

Natural Product: NPC172626

Natural Product ID:	NPC172626
Common Name:	Aplysinone B
IUPAC Name:	(5S,6R,7S)-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-oxo-1-oxa-2-azaspiro[4.5]deca-2,9-diene-3-carboxamide
Synonyms:
Molecular Formula:	C23H24Br4N4O8
Standard InCHIKey:	XZZXVTRWUWMFQH-IXJQUZSASA-N
Standard InCHI:	InChI=1S/C23H24Br4N4O8/c24-10-6-22(18(34)14(26)16(10)32)8-12(30-38-22)20(36)28-4-2-1-3-5-29-21(37)13-9-23(39-31-13)7-11(25)17(33)15(27)19(23)35/h6-7,14-15,18-19,34-35H,1-5,8-9H2,(H,28,36)(H,29,37)/t14-,15-,18+,19+,22-,23-/m1/s1
Canonical SMILES:	O=C(C1=NO[C@@]2(C1)C=C(Br)C(=O)[C@H]([C@@H]2O)Br)NCCCCCNC(=O)C1=NO[C@@]2(C1)C=C(Br)C(=O)[C@H]([C@@H]2O)Br
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	=	3000	nM	10924160
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	2100	nM	10924160
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	1500	nM	10924160
NPT81	Cell Line	A549	Homo sapiens	LC50	=	4100	nM	10924160
NPT81	Cell Line	A549	Homo sapiens	TGI	=	2900	nM	10924160
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	3000	nM	10924160
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	2100	nM	10924160
NPT81	Cell Line	A549	Homo sapiens	GI50	=	2000	nM	10924160
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	1600	nM	22584254

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 NPC172626 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	95
0.1-0.2	653
0.2-0.3	8483
0.3-0.4	17835
0.4-0.5	3633
0.5-0.6	168
0.6-0.7	3
0.7-0.8	7
0.8-0.85	5
0.85-0.9	2
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470892
0.9302	High Similarity	NPC473261
0.9302	High Similarity	NPC300912
0.9302	High Similarity	NPC202166
0.9302	High Similarity	NPC473262
0.8561	High Similarity	NPC473683
0.8507	High Similarity	NPC289324
0.8478	Intermediate Similarity	NPC130714
0.8372	Intermediate Similarity	NPC1702
0.8372	Intermediate Similarity	NPC158672
0.8248	Intermediate Similarity	NPC470886
0.8182	Intermediate Similarity	NPC477220
0.7537	Intermediate Similarity	NPC313173
0.7519	Intermediate Similarity	NPC66855
0.7426	Intermediate Similarity	NPC260270
0.7353	Intermediate Similarity	NPC145149
0.7324	Intermediate Similarity	NPC181086
0.7222	Intermediate Similarity	NPC81079
0.7203	Intermediate Similarity	NPC304257
0.6772	Remote Similarity	NPC243106
0.6772	Remote Similarity	NPC45830
0.6133	Remote Similarity	NPC202866
0.5942	Remote Similarity	NPC133729
0.5839	Remote Similarity	NPC475610
0.5833	Remote Similarity	NPC259071
0.5833	Remote Similarity	NPC77435
0.5801	Remote Similarity	NPC174607
0.5769	Remote Similarity	NPC147847
0.5755	Remote Similarity	NPC207820
0.5755	Remote Similarity	NPC140251
0.5755	Remote Similarity	NPC307903
0.5652	Remote Similarity	NPC472616
0.5645	Remote Similarity	NPC227953
0.5629	Remote Similarity	NPC473249
0.5612	Remote Similarity	NPC472615
0.5608	Remote Similarity	NPC160688

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC172626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	359
0.2-0.3	3537
0.3-0.4	4563
0.4-0.5	592
0.5-0.6	22
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
0.5676	Remote Similarity	NPD7623	Phase 3
0.5676	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD7746	Phase 1
0.5629	Remote Similarity	NPD7747	Phase 1

Structure

NPC172626 OpenBabel07101718322D 39 42 0 0 1 0 0 0 0 0999 V2000 -3.6929 -3.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2807 -2.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6984 -3.3988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8739 -1.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2916 -2.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9456 -4.1922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8411 -2.1977 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 -7.8117 -4.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8630 -1.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6777 -3.1922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6777 -4.1922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8117 -2.6922 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4562 -1.0762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4727 -0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9456 -3.1922 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8117 -5.6922 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -0.4945 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -9.5437 -2.6922 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -3.4945 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.4617 -0.9717 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8794 -1.6762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3630 -2.8558 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.5437 -4.6922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8117 -1.6922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0440 -0.2672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0605 0.0464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0321 -3.5989 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 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 16 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 20 1 0 0 0 0 12 30 2 0 0 0 0 13 21 1 0 0 0 0 13 31 2 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 14 26 1 1 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 32 2 0 0 0 0 17 33 2 0 0 0 0 18 22 1 6 0 0 0 18 34 1 0 0 0 0 19 23 1 6 0 0 0 19 35 1 0 0 0 0 20 28 1 0 0 0 0 20 36 2 0 0 0 0 21 29 1 0 0 0 0 21 37 2 0 0 0 0 22 6 1 6 0 0 0 22 38 1 0 0 0 0 23 7 1 6 0 0 0 23 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	23661639
ChEMBL	CHEMBL388324
ZINC

Physicochemical Properties

Molecular Weight:	799.83
ALogP:	-1.3746
MLogP:	2.23
XLogP:	1.218
# Rotatable Bonds:	16
Polar Surface Area:	175.98
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	39

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