NPASS Natural Product

Natural Product: NPC121402

Natural Product ID:	NPC121402
Common Name:	Sesterstatin 3
IUPAC Name:	(5aS,5bR,7aR,8R,11aR,11bR,13R,13aS)-13-hydroxy-8-(hydroxymethyl)-5b,8,11a,13a-tetramethyl-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[1,2-g][2]benzofuran-1-one
Synonyms:	Sesterstatin 3
Molecular Formula:	C25H38O4
Standard InCHIKey:	BHUWRPVVYSATJU-PWBGEZQRSA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-22(14-26)9-5-10-23(2)16(22)8-11-24(3)17-7-6-15-13-29-21(28)20(15)25(17,4)19(27)12-18(23)24/h16-19,26-27H,5-14H2,1-4H3/t16-,17-,18+,19+,22-,23-,24-,25+/m0/s1
Canonical SMILES:	OC[C@]1(C)CCC[C@]2([C@H]1CC[C@@]1([C@@H]2C[C@H]([C@]2([C@H]1CCC1=C2C(=O)OC1)C)O)C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota		Indian Ocean		PMID[16124771]
NPO5239	Hyrtios erectus	Species	Thorectidae	Eukaryota				PMID[9461648]

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Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell Line	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.3	ug/ml	9461648
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.3	ug/ml	16124771

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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 NPC121402 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	142
0.1-0.2	821
0.2-0.3	2646
0.3-0.4	5102
0.4-0.5	10169
0.5-0.6	4508
0.6-0.7	4351
0.7-0.8	2793
0.8-0.85	323
0.85-0.9	24
0.9-0.95	2
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.8119	Intermediate Similarity	NPC54909
0.8119	Intermediate Similarity	NPC473160
0.8119	Intermediate Similarity	NPC472637
0.8119	Intermediate Similarity	NPC233012
0.8125	Intermediate Similarity	NPC470589

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Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC121402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1360
0.2-0.3	3383
0.3-0.4	2666
0.4-0.5	1016
0.5-0.6	284
0.6-0.7	204
0.7-0.8	88
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.648	Remote Similarity	NPD7078	Approved
0.648	Remote Similarity	NPD8293	Discontinued
0.6486	Remote Similarity	NPD5344	Discontinued
0.6495	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6098	Approved

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Structure

CID121402 OpenBabel06191715472D 29 33 0 0 1 0 0 0 0 0999 V2000 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2350 -1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 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 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 1 0 0 0 16 23 1 0 0 0 0 17 24 1 1 0 0 0 17 25 1 0 0 0 0 18 23 1 1 0 0 0 18 24 1 0 0 0 0 19 25 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 1 1 1 0 0 0 23 2 1 1 0 0 0 24 3 1 1 0 0 0 25 4 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	10092532
ChEMBL	CHEMBL485795
ZINC

Physicochemical Properties

Molecular Weight:	402.28
ALogP:	0.4622
MLogP:	3.77
XLogP:	4.832
# Rotatable Bonds:	7
Polar Surface Area:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	29

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