NPASS Natural Product

Natural Product: NPC9868

Natural Product ID:	NPC9868
Common Name:	Sinuflexolide
IUPAC Name:	(1S,4S,5R,8E,12R,13R)-4,5,12-trihydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadec-8-en-15-one
Synonyms:	Sinuflexolide
Molecular Formula:	C20H32O5
Standard InCHIKey:	DAMCLDLKMZAXNC-JZVIKIFUSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-13-6-5-10-20(4,24)17-12-15(14(2)18(22)25-17)9-11-19(3,23)16(21)8-7-13/h6,15-17,21,23-24H,2,5,7-12H2,1,3-4H3/b13-6+/t15-,16+,17+,19-,20+/m0/s1
Canonical SMILES:	C/C/1=CCC[C@@](C)(O)[C@H]2C[C@H](CC[C@]([C@@H](CC1)O)(C)O)C(=C)C(=O)O2
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
NPO3821	Sinularia flexibilis	Species	Alcyoniidae	Eukaryota				PMID[9644083]

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Biological Activity

Activity Type	# Activity
ED50	4

Activity Type	# Activity
Cell Line	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.39	ug/ml	11858989
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.16	ug/ml	26351040
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.68	ug/ml	4020828
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.46	ug/ml	11858989

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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 NPC9868 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	107
0.1-0.2	691
0.2-0.3	2651
0.3-0.4	5588
0.4-0.5	10698
0.5-0.6	4880
0.6-0.7	5084
0.7-0.8	1108
0.8-0.85	55
0.85-0.9	20
0.9-0.95	4
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.7647	Intermediate Similarity	NPC11796
0.7647	Intermediate Similarity	NPC474341
0.7653	Intermediate Similarity	NPC475945
0.7653	Intermediate Similarity	NPC475871
0.7654	Intermediate Similarity	NPC4299

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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 NPC9868 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	114
0.1-0.2	1189
0.2-0.3	3405
0.3-0.4	2847
0.4-0.5	1005
0.5-0.6	374
0.6-0.7	201
0.7-0.8	24
0.8-0.85	2
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
0.6087	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6317	Approved
0.6098	Remote Similarity	NPD6109	Phase 1
0.6098	Remote Similarity	NPD7260	Phase 2
0.61	Remote Similarity	NPD6051	Approved

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Structure

NPC9868 OpenBabel07101719512D 25 26 0 0 1 0 0 0 0 0999 V2000 -1.8772 -1.2316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3756 2.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4435 1.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5331 -0.0756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2679 -0.7197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8280 -0.7197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7146 -0.0756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8878 0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5479 1.9452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2439 -0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0959 1.8287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7919 1.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3398 -0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7919 1.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8287 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8292 1.0143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7919 0.4572 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7919 0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5491 1.4994 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6187 -0.0756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6988 1.2968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3756 -0.4572 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8317 2.3690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0759 -0.8674 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 13 1 0 0 0 0 2 14 2 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 9 1 1 0 0 0 16 19 1 1 0 0 0 16 21 1 0 0 0 0 17 20 1 6 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 20 4 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	21774929
ChEMBL	CHEMBL470131
ZINC

Physicochemical Properties

Molecular Weight:	352.22
ALogP:	0.9088
MLogP:	3.11
XLogP:	2.468
# Rotatable Bonds:	6
Polar Surface Area:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	25

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