NPASS Natural Product

Natural Product: NPC117746

Natural Product ID:	NPC117746
Common Name:	Sarcostolide A
IUPAC Name:	(1S,2R,5Z,9E)-5,9-dimethyl-2-propan-2-yl-15-oxabicyclo[11.2.1]hexadeca-5,9,13(16)-triene-4,11,14-trione
Synonyms:
Molecular Formula:	C20H26O4
Standard InCHIKey:	SLQVZPZHWRKZDO-XISQCUFKSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-12(2)17-11-18(22)14(4)7-5-6-13(3)8-16(21)9-15-10-19(17)24-20(15)23/h7-8,10,12,17,19H,5-6,9,11H2,1-4H3/b13-8+,14-7-/t17-,19-/m1/s1
Canonical SMILES:	O=C1/C=C(C)/CC/C=C(/C)C(=O)C[C@@H]([C@H]2C=C(C1)C(=O)O2)C(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
NPO29001	Sarcophyton stolidotum	Species	Orchidaceae	Eukaryota		Taiwan		PMID[18537291]

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Biological Activity

Activity Type	# Activity
Others	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
NPT1183	Cell Line	WiDr	Homo sapiens	Inhibition	=	19.97	%	DrugMatrix in vitro pharmacology data
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	22.26	%	18973388

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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 NPC117746 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	100
0.1-0.2	743
0.2-0.3	3849
0.3-0.4	11063
0.4-0.5	7284
0.5-0.6	4949
0.6-0.7	2352
0.7-0.8	490
0.8-0.85	44
0.85-0.9	6
0.9-0.95	5
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.747	Intermediate Similarity	NPC16488
0.747	Intermediate Similarity	NPC59097
0.747	Intermediate Similarity	NPC131669
0.747	Intermediate Similarity	NPC473390
0.7471	Intermediate Similarity	NPC144133

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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 NPC117746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	1298
0.2-0.3	4115
0.3-0.4	2538
0.4-0.5	704
0.5-0.6	300
0.6-0.7	79
0.7-0.8	6
0.8-0.85	1
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
0.56	Remote Similarity	NPD5654	Approved
0.56	Remote Similarity	NPD5210	Approved
0.56	Remote Similarity	NPD4629	Approved
0.5604	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7320	Approved

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Structure

NPC117746 OpenBabel07101718292D 24 25 0 0 1 0 0 0 0 0999 V2000 2.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -2.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 1.2660 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 -1.4198 -1.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 0.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 -1.6920 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 -0.0186 0.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 -1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 0.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 -1.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 0.6920 0.0000 C 0 0 2 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 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 -2.8634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8968 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 12 1 6 0 0 0 17 19 1 0 0 0 0 18 22 2 0 0 0 0 19 10 1 1 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24970448
ChEMBL	CHEMBL487628
ZINC

Physicochemical Properties

Molecular Weight:	330.18
ALogP:	1.9792
MLogP:	3.22
XLogP:	2.914
# Rotatable Bonds:	5
Polar Surface Area:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	24

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