NPASS Natural Product

Natural Product: NPC33876

Natural Product ID:	NPC33876
Common Name:	8-Acetylcaespitol
IUPAC Name:	[(2R,3R,5R)-5-bromo-2-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-2,6,6-trimethyloxan-3-yl] acetate
Synonyms:	8-Acetylcaespitol
Molecular Formula:	C17H27Br2ClO3
Standard InCHIKey:	PVGGMHHFCWKSQT-BUJMLFLGSA-N
Standard InCHI:	InChI=1S/C17H27Br2ClO3/c1-10(21)22-14-9-12(18)15(2,3)23-17(14,5)11-6-7-16(4,20)13(19)8-11/h11-14H,6-9H2,1-5H3/t11-,12+,13-,14+,16-,17+/m0/s1
Canonical SMILES:	CC(=O)O[C@@H]1C[C@@H](Br)C(O[C@]1(C)[C@H]1CC[C@]([C@H](C1)Br)(C)Cl)(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
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota				PMID[16309323]
NPO18850	Aplysia dactylomela	Species	Aplysiidae	Eukaryota		Tenerife		PMID[10924166]

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	33600	nM	DrugMatrix in vivo data: Biochemistry
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	31900	nM	21123068
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	42000	nM	21123068
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	42000	nM	19349520

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 NPC33876 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	196
0.1-0.2	2927
0.2-0.3	14112
0.3-0.4	7300
0.4-0.5	5969
0.5-0.6	358
0.6-0.7	16
0.7-0.8	2
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC277993
0.9189	High Similarity	NPC469580
0.8904	High Similarity	NPC469581
0.8718	High Similarity	NPC469556
0.8608	High Similarity	NPC469555
0.8493	Intermediate Similarity	NPC83368
0.8088	Intermediate Similarity	NPC308569
0.8088	Intermediate Similarity	NPC469572
0.8088	Intermediate Similarity	NPC469582
0.7564	Intermediate Similarity	NPC150938
0.7123	Intermediate Similarity	NPC469573
0.6854	Remote Similarity	NPC76909
0.6782	Remote Similarity	NPC282598
0.6582	Remote Similarity	NPC475786
0.6429	Remote Similarity	NPC291724
0.6429	Remote Similarity	NPC274261
0.6353	Remote Similarity	NPC244002
0.6265	Remote Similarity	NPC123122
0.6186	Remote Similarity	NPC475934
0.6154	Remote Similarity	NPC469570
0.6154	Remote Similarity	NPC48210
0.6136	Remote Similarity	NPC15714
0.6023	Remote Similarity	NPC83436
0.6	Remote Similarity	NPC237510
0.6	Remote Similarity	NPC472945
0.6	Remote Similarity	NPC472944
0.6	Remote Similarity	NPC475793
0.5978	Remote Similarity	NPC93616
0.5974	Remote Similarity	NPC185116
0.5914	Remote Similarity	NPC246347
0.5914	Remote Similarity	NPC279260
0.5904	Remote Similarity	NPC253123
0.5897	Remote Similarity	NPC204173
0.5882	Remote Similarity	NPC470526
0.5882	Remote Similarity	NPC476718
0.5862	Remote Similarity	NPC30575
0.5854	Remote Similarity	NPC476928
0.5851	Remote Similarity	NPC471377
0.5851	Remote Similarity	NPC280810
0.5843	Remote Similarity	NPC476603
0.5783	Remote Similarity	NPC301725
0.5773	Remote Similarity	NPC469538
0.5765	Remote Similarity	NPC470173
0.5698	Remote Similarity	NPC109510
0.5696	Remote Similarity	NPC472021
0.5682	Remote Similarity	NPC136424
0.5682	Remote Similarity	NPC476606
0.5667	Remote Similarity	NPC477287
0.5641	Remote Similarity	NPC240206
0.5618	Remote Similarity	NPC476719
0.561	Remote Similarity	NPC469926
0.5604	Remote Similarity	NPC471217
0.5604	Remote Similarity	NPC471216
0.5604	Remote Similarity	NPC472943
0.5604	Remote Similarity	NPC472951

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC33876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	4067
0.2-0.3	3654
0.3-0.4	897
0.4-0.5	290
0.5-0.6	19
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

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5679	Remote Similarity	NPD371	Approved

Structure

NPC33876 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 2.5981 2.5000 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 -3.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 1.8660 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5000 1.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -3.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 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 -3.0000 2.7321 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 0.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 15 1 0 0 0 0 3 15 1 0 0 0 0 6 7 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 21 2 0 0 0 0 10 22 1 0 0 0 0 11 6 1 1 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 1 0 0 0 13 16 1 1 0 0 0 13 19 1 0 0 0 0 14 17 1 6 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 4 1 1 0 0 0 16 20 1 0 0 0 0 17 5 1 1 0 0 0 17 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	23244756
ChEMBL	CHEMBL462893
ZINC

Physicochemical Properties

Molecular Weight:	472.00
ALogP:	3.2114
MLogP:	2.67
XLogP:	5.651
# Rotatable Bonds:	11
Polar Surface Area:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	23

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