NPASS Natural Product

Natural Product: NPC469927

Natural Product ID:	NPC469927
Common Name:	(4S,5S)-4-Hydroxy-5-[(2R)-2-Hydroxy-11-(4-Hydroxyphenyl)-2-Methylundecyl]-5-Methyloxolan-2-One
IUPAC Name:	(4S,5S)-4-hydroxy-5-[(2R)-2-hydroxy-11-(4-hydroxyphenyl)-2-methylundecyl]-5-methyloxolan-2-one
Synonyms:
Molecular Formula:	C23H36O5
Standard InCHIKey:	DIFCTNZAEJDHLR-WWNPGLIZSA-N
Standard InCHI:	InChI=1S/C23H36O5/c1-22(27,17-23(2)20(25)16-21(26)28-23)15-9-7-5-3-4-6-8-10-18-11-13-19(24)14-12-18/h11-14,20,24-25,27H,3-10,15-17H2,1-2H3/t20-,22+,23-/m0/s1
Canonical SMILES:	Oc1ccc(cc1)CCCCCCCCC[C@](C[C@]1(C)OC(=O)C[C@@H]1O)(O)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
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota		Puerto Rican		PMID[20923180]

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Biological Activity

Activity Type	# Activity
IC50	3
Others	2

Activity Type	# Activity
Cell Line	4
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1383	Cell Line	A2058	Homo sapiens	Activity	=	81	%	15104488
NPT1383	Cell Line	A2058	Homo sapiens	IC50	>	10000	nM	10.6019/CHEMBL1201861
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7	ug/ml	10924160
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	10000	nM	PubChem BioAssay data set
NPT90	Cell Line	DU-145	Homo sapiens	Activity	=	95	%	19029328

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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 NPC469927 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	156
0.1-0.2	609
0.2-0.3	1620
0.3-0.4	3575
0.4-0.5	8073
0.5-0.6	5441
0.6-0.7	9277
0.7-0.8	2062
0.8-0.85	67
0.85-0.9	8
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.7769	Intermediate Similarity	NPC138798
0.7769	Intermediate Similarity	NPC244876
0.777	Intermediate Similarity	NPC295492
0.777	Intermediate Similarity	NPC303683
0.777	Intermediate Similarity	NPC474875

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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 NPC469927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	607
0.2-0.3	1313
0.3-0.4	2431
0.4-0.5	2431
0.5-0.6	1424
0.6-0.7	689
0.7-0.8	109
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
0.6736	Remote Similarity	NPD275	Approved
0.6736	Remote Similarity	NPD274	Approved
0.6738	Remote Similarity	NPD2614	Approved
0.6738	Remote Similarity	NPD5203	Approved
0.6738	Remote Similarity	NPD4620	Approved

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Structure

NPC469927 OpenBabel07101718282D 28 29 0 0 1 0 0 0 0 0999 V2000 2.3605 -2.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4696 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3356 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6036 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2016 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7375 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0677 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9337 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6657 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7997 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5318 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6657 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7997 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5318 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 -1.6045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3978 -0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8605 -1.6045 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 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 6 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 1 1 1 0 0 0 22 27 1 0 0 0 0 23 2 1 1 0 0 0 23 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	49831497
ChEMBL	CHEMBL1271159
ZINC

Physicochemical Properties

Molecular Weight:	392.26
ALogP:	-2.814
MLogP:	3.44
XLogP:	5.968
# Rotatable Bonds:	17
Polar Surface Area:	86.99
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	28

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