NPASS Natural Product

Natural Product: NPC469555

Natural Product ID:	NPC469555
Common Name:	(5S)-5-Acetoxycaespitol
IUPAC Name:	[(1S,2S,4R,5R)-4-bromo-2-[(2S,3S,5S)-5-bromo-3-hydroxy-2,6,6-trimethyloxan-2-yl]-5-chloro-5-methylcyclohexyl] acetate
Synonyms:	(5S)-5-Acetoxycaespitol
Molecular Formula:	C17H27Br2ClO4
Standard InCHIKey:	TXUIEJDHDWIUIB-NCIZBFQTSA-N
Standard InCHI:	InChI=1S/C17H27Br2ClO4/c1-9(21)23-11-8-16(4,20)13(19)6-10(11)17(5)14(22)7-12(18)15(2,3)24-17/h10-14,22H,6-8H2,1-5H3/t10-,11-,12-,13+,14-,16+,17-/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]1O)Br)Br
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
NPO29486	Laurencia catarinensis	Species	Rhodomelaceae	Eukaryota		Brazil		PMID[20039643]

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11700	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	12400	nM	17570664
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	13100	nM	16107142

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 NPC469555 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	211
0.1-0.2	2479
0.2-0.3	10045
0.3-0.4	9624
0.4-0.5	7038
0.5-0.6	1422
0.6-0.7	62
0.7-0.8	2
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC469556
0.9367	High Similarity	NPC469580
0.8861	High Similarity	NPC469581
0.8608	High Similarity	NPC33876
0.8608	High Similarity	NPC277993
0.8481	Intermediate Similarity	NPC83368
0.7619	Intermediate Similarity	NPC150938
0.7143	Intermediate Similarity	NPC475934
0.6962	Remote Similarity	NPC308569
0.6962	Remote Similarity	NPC469582
0.6962	Remote Similarity	NPC469572
0.6737	Remote Similarity	NPC279260
0.6667	Remote Similarity	NPC471377
0.6667	Remote Similarity	NPC244002
0.6632	Remote Similarity	NPC93616
0.6562	Remote Similarity	NPC246347
0.6556	Remote Similarity	NPC136424
0.6543	Remote Similarity	NPC185116
0.6517	Remote Similarity	NPC237510
0.6517	Remote Similarity	NPC472945
0.6517	Remote Similarity	NPC475793
0.6517	Remote Similarity	NPC472944
0.6452	Remote Similarity	NPC472943
0.6452	Remote Similarity	NPC472951
0.6413	Remote Similarity	NPC43463
0.6413	Remote Similarity	NPC191345
0.6413	Remote Similarity	NPC252483
0.6395	Remote Similarity	NPC476928
0.6383	Remote Similarity	NPC470156
0.6333	Remote Similarity	NPC166250
0.6316	Remote Similarity	NPC470155
0.6316	Remote Similarity	NPC477446
0.6316	Remote Similarity	NPC477447
0.6304	Remote Similarity	NPC476719
0.6292	Remote Similarity	NPC470173
0.6263	Remote Similarity	NPC76909
0.625	Remote Similarity	NPC253123
0.6224	Remote Similarity	NPC471411
0.6224	Remote Similarity	NPC471410
0.6222	Remote Similarity	NPC123122
0.6211	Remote Similarity	NPC470154
0.6211	Remote Similarity	NPC211049
0.6207	Remote Similarity	NPC179823
0.619	Remote Similarity	NPC469573
0.6186	Remote Similarity	NPC282598
0.6186	Remote Similarity	NPC18953
0.617	Remote Similarity	NPC83436
0.6146	Remote Similarity	NPC60018
0.6146	Remote Similarity	NPC202688
0.6146	Remote Similarity	NPC154043
0.6136	Remote Similarity	NPC475786
0.6129	Remote Similarity	NPC171658
0.6105	Remote Similarity	NPC186594
0.61	Remote Similarity	NPC475817
0.6082	Remote Similarity	NPC477285
0.6082	Remote Similarity	NPC111582
0.6064	Remote Similarity	NPC177343
0.6061	Remote Similarity	NPC155531
0.6061	Remote Similarity	NPC215968
0.6061	Remote Similarity	NPC475276
0.6044	Remote Similarity	NPC476422
0.6042	Remote Similarity	NPC119922
0.6042	Remote Similarity	NPC116320
0.6022	Remote Similarity	NPC470176
0.6	Remote Similarity	NPC45833
0.6	Remote Similarity	NPC471879
0.6	Remote Similarity	NPC213658
0.6	Remote Similarity	NPC110365
0.6	Remote Similarity	NPC329871
0.6	Remote Similarity	NPC62202
0.5979	Remote Similarity	NPC477286
0.5979	Remote Similarity	NPC286719
0.5979	Remote Similarity	NPC216800
0.596	Remote Similarity	NPC266651
0.596	Remote Similarity	NPC313115
0.596	Remote Similarity	NPC476715
0.5957	Remote Similarity	NPC307865
0.5949	Remote Similarity	NPC291724
0.5949	Remote Similarity	NPC274261
0.5941	Remote Similarity	NPC476379
0.5934	Remote Similarity	NPC131506
0.5934	Remote Similarity	NPC157777
0.5918	Remote Similarity	NPC2572
0.5918	Remote Similarity	NPC29342
0.5918	Remote Similarity	NPC69953
0.5914	Remote Similarity	NPC472950
0.5914	Remote Similarity	NPC472952
0.59	Remote Similarity	NPC477283
0.5895	Remote Similarity	NPC471045
0.5895	Remote Similarity	NPC272841
0.5882	Remote Similarity	NPC204173
0.5876	Remote Similarity	NPC190940
0.587	Remote Similarity	NPC476718
0.5859	Remote Similarity	NPC79308
0.5851	Remote Similarity	NPC470174
0.5851	Remote Similarity	NPC474020
0.5851	Remote Similarity	NPC30575
0.5842	Remote Similarity	NPC5943
0.5833	Remote Similarity	NPC476603
0.5833	Remote Similarity	NPC47663
0.581	Remote Similarity	NPC191915
0.581	Remote Similarity	NPC96736
0.581	Remote Similarity	NPC247877
0.581	Remote Similarity	NPC309127
0.581	Remote Similarity	NPC178949
0.581	Remote Similarity	NPC151214
0.5806	Remote Similarity	NPC74639
0.5806	Remote Similarity	NPC308489
0.5806	Remote Similarity	NPC470151
0.58	Remote Similarity	NPC51267
0.5789	Remote Similarity	NPC474003
0.5784	Remote Similarity	NPC476435
0.5784	Remote Similarity	NPC201607
0.5784	Remote Similarity	NPC471221
0.5784	Remote Similarity	NPC470872
0.5784	Remote Similarity	NPC56777
0.5773	Remote Similarity	NPC474714
0.5769	Remote Similarity	NPC473066
0.5769	Remote Similarity	NPC312805
0.5765	Remote Similarity	NPC470363
0.5758	Remote Similarity	NPC128816
0.5758	Remote Similarity	NPC273356
0.5758	Remote Similarity	NPC30102
0.5758	Remote Similarity	NPC97491
0.5758	Remote Similarity	NPC67158
0.5758	Remote Similarity	NPC259173
0.5758	Remote Similarity	NPC241959
0.5755	Remote Similarity	NPC94582
0.5755	Remote Similarity	NPC57964
0.5747	Remote Similarity	NPC235788
0.5743	Remote Similarity	NPC103782
0.5743	Remote Similarity	NPC228593
0.5743	Remote Similarity	NPC64862
0.5743	Remote Similarity	NPC475684
0.5743	Remote Similarity	NPC114378
0.5743	Remote Similarity	NPC131365
0.5743	Remote Similarity	NPC235196
0.5728	Remote Similarity	NPC224552
0.5728	Remote Similarity	NPC239453
0.5714	Remote Similarity	NPC118116
0.5714	Remote Similarity	NPC73515
0.5714	Remote Similarity	NPC475307
0.5714	Remote Similarity	NPC216941
0.5714	Remote Similarity	NPC211845
0.5714	Remote Similarity	NPC122083
0.5714	Remote Similarity	NPC256104
0.5714	Remote Similarity	NPC470833
0.5714	Remote Similarity	NPC182740
0.5701	Remote Similarity	NPC203434
0.5701	Remote Similarity	NPC238796
0.5701	Remote Similarity	NPC237071
0.5701	Remote Similarity	NPC156377
0.5701	Remote Similarity	NPC252056
0.57	Remote Similarity	NPC115995
0.5686	Remote Similarity	NPC44538
0.5686	Remote Similarity	NPC280810
0.5684	Remote Similarity	NPC476606
0.5682	Remote Similarity	NPC94897
0.5673	Remote Similarity	NPC473269
0.567	Remote Similarity	NPC81074
0.567	Remote Similarity	NPC477282
0.567	Remote Similarity	NPC31330
0.567	Remote Similarity	NPC220379
0.567	Remote Similarity	NPC476176
0.5667	Remote Similarity	NPC469925
0.566	Remote Similarity	NPC211238
0.5657	Remote Similarity	NPC164289
0.5657	Remote Similarity	NPC2096
0.5657	Remote Similarity	NPC242771
0.5657	Remote Similarity	NPC475849
0.5657	Remote Similarity	NPC100366
0.5657	Remote Similarity	NPC311642
0.5657	Remote Similarity	NPC208912
0.5648	Remote Similarity	NPC92231
0.5648	Remote Similarity	NPC34732
0.5644	Remote Similarity	NPC477205
0.5644	Remote Similarity	NPC290612
0.5644	Remote Similarity	NPC235402
0.5644	Remote Similarity	NPC471379
0.5644	Remote Similarity	NPC196911
0.5638	Remote Similarity	NPC31046
0.5638	Remote Similarity	NPC200167
0.5638	Remote Similarity	NPC71152
0.5638	Remote Similarity	NPC209666
0.5638	Remote Similarity	NPC53868
0.5631	Remote Similarity	NPC470260
0.5631	Remote Similarity	NPC92370
0.5631	Remote Similarity	NPC476724
0.5631	Remote Similarity	NPC476723
0.5631	Remote Similarity	NPC75443
0.5631	Remote Similarity	NPC255176
0.5631	Remote Similarity	NPC131453
0.5625	Remote Similarity	NPC133596
0.5625	Remote Similarity	NPC212453
0.5625	Remote Similarity	NPC11907
0.5625	Remote Similarity	NPC214030
0.5625	Remote Similarity	NPC474574
0.5625	Remote Similarity	NPC64081
0.5625	Remote Similarity	NPC83108
0.5625	Remote Similarity	NPC40049

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	3652
0.2-0.3	3797
0.3-0.4	1015
0.4-0.5	415
0.5-0.6	39
0.6-0.7	1
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
0.6429	Remote Similarity	NPD371	Approved
0.5824	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3669	Approved
0.5758	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD1810	Approved
0.5638	Remote Similarity	NPD1811	Approved

Structure

NPC469555 OpenBabel07101718332D 24 25 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 0.3660 -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 -0.9659 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 21 2 0 0 0 0 9 23 1 0 0 0 0 10 6 1 6 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 23 1 1 0 0 0 12 15 1 0 0 0 0 12 18 1 6 0 0 0 13 16 1 6 0 0 0 13 19 1 0 0 0 0 14 17 1 1 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 16 4 1 6 0 0 0 16 20 1 0 0 0 0 17 5 1 6 0 0 0 17 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	46881024
ChEMBL	CHEMBL1087144
ZINC

Physicochemical Properties

Molecular Weight:	488.00
ALogP:	2.4451
MLogP:	2.56
XLogP:	4.621
# Rotatable Bonds:	12
Polar Surface Area:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	24

Download Data

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