NPASS Natural Product

Natural Product: NPC469580

Natural Product ID:	NPC469580
Common Name:	(5S)-5-Acetoxyacetylcaespitol
IUPAC Name:	[(2S,3S,5S)-2-[(1S,2S,4R,5R)-2-acetyloxy-5-bromo-4-chloro-4-methylcyclohexyl]-5-bromo-2,6,6-trimethyloxan-3-yl] acetate
Synonyms:	(5S)-5-Acetoxyacetylcaespitol
Molecular Formula:	C19H29Br2ClO5
Standard InCHIKey:	OMBBHMVIDWGJKW-NPFZYRJPSA-N
Standard InCHI:	InChI=1S/C19H29Br2ClO5/c1-10(23)25-13-9-18(5,22)15(21)7-12(13)19(6)16(26-11(2)24)8-14(20)17(3,4)27-19/h12-16H,7-9H2,1-6H3/t12-,13-,14-,15+,16-,18+,19-/m0/s1
Canonical SMILES:	CC(=O)O[C@H]1C[C@@](C)(Cl)[C@@H](C[C@@H]1[C@]1(C)OC(C)(C)[C@H](C[C@@H]1OC(=O)C)Br)Br
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
NPO29486	Laurencia catarinensis	Species	Rhodomelaceae	Eukaryota		Brazil		PMID[20039643]

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Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

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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	IC50	>	100000	nM	12570376
NPT762	Cell Line	A-431	Homo sapiens	IC50	>	100000	nM	16107142
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000	nM	PubChem BioAssay data set

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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 NPC469580 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	230
0.1-0.2	2954
0.2-0.3	12759
0.3-0.4	7962
0.4-0.5	6458
0.5-0.6	497
0.6-0.7	19
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	5
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.56	Remote Similarity	NPC475817
0.5604	Remote Similarity	NPC74639
0.5604	Remote Similarity	NPC55508
0.561	Remote Similarity	NPC240206
0.5618	Remote Similarity	NPC5209

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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 NPC469580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	4081
0.2-0.3	3635
0.3-0.4	863
0.4-0.5	295
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

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5618	Remote Similarity	NPD2687	Approved
0.5618	Remote Similarity	NPD2686	Approved
0.5618	Remote Similarity	NPD2254	Approved
0.5833	Remote Similarity	NPD371	Approved

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Structure

NPC469580 OpenBabel07101719132D 27 28 0 0 1 0 0 0 0 0999 V2000 -1.7424 -2.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8637 0.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1907 -0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -1.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.7412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2247 -0.2247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6390 1.1895 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 0.2235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 1.8966 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 -0.4836 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.0694 -2.6049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 -0.9319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 23 2 0 0 0 0 10 25 1 0 0 0 0 11 24 2 0 0 0 0 11 26 1 0 0 0 0 12 7 1 6 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 25 1 1 0 0 0 14 17 1 0 0 0 0 14 20 1 6 0 0 0 15 18 1 6 0 0 0 15 21 1 0 0 0 0 16 19 1 1 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 5 1 6 0 0 0 18 22 1 0 0 0 0 19 6 1 6 0 0 0 19 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	46881053
ChEMBL	CHEMBL1088317
ZINC

Physicochemical Properties

Molecular Weight:	530.01
ALogP:	2.8242
MLogP:	2.67
XLogP:	5.361
# Rotatable Bonds:	14
Polar Surface Area:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	27

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