NPASS Natural Product

Natural Product: NPC103268

Natural Product ID:	NPC103268
Common Name:	Dolastatin 3
IUPAC Name:
Synonyms:	Dolastatin 3
Molecular Formula:	C29H40N8O6S2
Standard InCHIKey:	ATCVYMAKQRUVDS-OSAZLGQLSA-N
Standard InCHI:	InChI=1S/C29H40N8O6S2/c1-14(2)10-17-25(40)33-16(7-8-21(30)38)28-35-18(13-45-28)24(39)31-11-22-32-19(12-44-22)26(41)36-23(15(3)4)29(43)37-9-5-6-20(37)27(42)34-17/h12-17,20,23H,5-11H2,1-4H3,(H2,30,38)(H,31,39)(H,33,40)(H,34,42)(H,36,41)/t16-,17-,20-,23-/m0/s1
Canonical SMILES:	CC(C[C@@H]1N=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C(O)c2csc(CN=C(c3nc([C@@H](N=C1O)CCC(=N)O)sc3)O)n2)C(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		Palau		PMID[10691729]

Biological Activity

Activity Type	# Activity
ED50	1
IC50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT23	Individual Protein	Integrase	Human immunodeficiency virus 1	IC50	=	5000000	nM	Open TG-GATES in vivo data: Biochemistry
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.7	ug/ml	PubChem BioAssay data set
NPT23	Individual Protein	Integrase	Human immunodeficiency virus 1	IC50	=	4100000	nM	24480359

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 NPC103268 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	128
0.1-0.2	20277
0.2-0.3	6566
0.3-0.4	3218
0.4-0.5	575
0.5-0.6	83
0.6-0.7	30
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8194	Intermediate Similarity	NPC475390
0.777	Intermediate Similarity	NPC89592
0.7761	Intermediate Similarity	NPC214375
0.7622	Intermediate Similarity	NPC120917
0.7609	Intermediate Similarity	NPC51692
0.7552	Intermediate Similarity	NPC74917
0.7234	Intermediate Similarity	NPC267605
0.7176	Intermediate Similarity	NPC96016
0.7143	Intermediate Similarity	NPC135558
0.7125	Intermediate Similarity	NPC237219
0.7099	Intermediate Similarity	NPC222391
0.7025	Intermediate Similarity	NPC50274
0.6975	Remote Similarity	NPC110129
0.6975	Remote Similarity	NPC201014
0.6867	Remote Similarity	NPC256912
0.679	Remote Similarity	NPC217981
0.6766	Remote Similarity	NPC34319
0.6726	Remote Similarity	NPC164006
0.6575	Remote Similarity	NPC137705
0.6532	Remote Similarity	NPC132662
0.6467	Remote Similarity	NPC275393
0.6463	Remote Similarity	NPC145047
0.6463	Remote Similarity	NPC86490
0.6369	Remote Similarity	NPC56058
0.6369	Remote Similarity	NPC522
0.6264	Remote Similarity	NPC122427
0.6264	Remote Similarity	NPC329961
0.625	Remote Similarity	NPC161242
0.625	Remote Similarity	NPC469801
0.6243	Remote Similarity	NPC476103
0.6196	Remote Similarity	NPC165538
0.618	Remote Similarity	NPC25316
0.618	Remote Similarity	NPC263485
0.618	Remote Similarity	NPC229160
0.6171	Remote Similarity	NPC134480
0.6158	Remote Similarity	NPC476080
0.6158	Remote Similarity	NPC475534
0.6136	Remote Similarity	NPC473704
0.6124	Remote Similarity	NPC475330
0.6089	Remote Similarity	NPC174652
0.6069	Remote Similarity	NPC475554
0.6023	Remote Similarity	NPC216720
0.5988	Remote Similarity	NPC210424
0.5939	Remote Similarity	NPC319751
0.5833	Remote Similarity	NPC119481
0.5819	Remote Similarity	NPC24990
0.5813	Remote Similarity	NPC235866
0.5789	Remote Similarity	NPC106235
0.5789	Remote Similarity	NPC239660
0.5782	Remote Similarity	NPC475196
0.5774	Remote Similarity	NPC473398
0.5729	Remote Similarity	NPC475350
0.5729	Remote Similarity	NPC14877
0.5729	Remote Similarity	NPC145178
0.569	Remote Similarity	NPC315252
0.5644	Remote Similarity	NPC251036
0.5631	Remote Similarity	NPC478030

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC103268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	111
0.1-0.2	1349
0.2-0.3	3674
0.3-0.4	3301
0.4-0.5	668
0.5-0.6	53
0.6-0.7	5
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
0.6507	Remote Similarity	NPD9579	Approved
0.6215	Remote Similarity	NPD2957	Phase 2
0.6193	Remote Similarity	NPD3876	Approved
0.6136	Remote Similarity	NPD3877	Approved
0.6034	Remote Similarity	NPD3966	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD3333	Approved
0.5754	Remote Similarity	NPD3332	Approved
0.5714	Remote Similarity	NPD6121	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD8030	Approved

Structure

NPC103268 OpenBabel07101719152D 45 48 0 0 1 0 0 0 0 0999 V2000 0.8636 3.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1218 5.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4983 -2.2668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8559 -3.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1355 1.1526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1747 5.2344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1303 5.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8944 -0.4473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4906 4.3935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2282 -0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9522 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2642 2.2244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4983 4.2445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4906 -2.4159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9522 4.2595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1141 3.6117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2282 2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9522 -2.2818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1490 0.9888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8634 4.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6649 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1141 -1.6340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5230 1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9801 4.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9550 -2.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8831 3.8941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6408 3.8741 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5230 0.4888 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8831 -1.9165 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9550 4.3342 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 2.8786 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6649 3.2706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9801 -2.1340 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8189 5.1437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5118 1.6379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6147 5.0426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8803 -3.3537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9556 2.2724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3924 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8086 -0.7986 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -4.5916 2.9492 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 7 8 1 0 0 0 0 8 21 1 0 0 0 0 9 37 1 0 0 0 0 10 14 1 0 0 0 0 11 22 1 0 0 0 0 11 31 1 0 0 0 0 12 19 2 0 0 0 0 12 44 1 0 0 0 0 13 18 2 0 0 0 0 13 45 1 0 0 0 0 16 7 1 6 0 0 0 16 28 1 0 0 0 0 16 33 1 0 0 0 0 17 10 1 6 0 0 0 17 25 1 0 0 0 0 17 34 1 0 0 0 0 18 24 1 0 0 0 0 18 35 1 0 0 0 0 19 26 1 0 0 0 0 19 32 1 0 0 0 0 20 6 1 6 0 0 0 20 27 1 0 0 0 0 20 37 1 0 0 0 0 21 30 2 0 0 0 0 21 38 1 0 0 0 0 22 32 2 0 0 0 0 22 44 1 0 0 0 0 23 15 1 6 0 0 0 23 29 1 0 0 0 0 23 36 1 0 0 0 0 24 31 2 3 0 0 0 24 39 1 0 0 0 0 25 33 2 3 0 0 0 25 40 1 0 0 0 0 26 36 2 3 0 0 0 26 41 1 0 0 0 0 27 34 2 3 0 0 0 27 42 1 0 0 0 0 28 35 2 0 0 0 0 28 45 1 0 0 0 0 29 37 1 0 0 0 0 29 43 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	9852693
ChEMBL	CHEMBL506581
ZINC

Physicochemical Properties

Molecular Weight:	660.25
ALogP:	-0.1242
MLogP:	2.89
XLogP:	3.016
# Rotatable Bonds:	15
Polar Surface Area:	277.01
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	45

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