NPASS Natural Product

Natural Product: NPC103605

Natural Product ID:	NPC103605
Common Name:	3-[(2R,3R,5S,6R)-6-[(2R)-Butan-2-Yl]-3,5-Dimethyloxan-2-Yl]-4-Hydroxy-1-Methoxy-5-Phenylpyridin-2-One
IUPAC Name:	3-[(2R,3R,5S,6R)-6-[(2R)-butan-2-yl]-3,5-dimethyloxan-2-yl]-4-hydroxy-1-methoxy-5-phenylpyridin-2-one
Synonyms:
Molecular Formula:	C23H31NO4
Standard InCHIKey:	WGEGPIRBSMWCPA-YFNGHYIGSA-N
Standard InCHI:	InChI=1S/C23H31NO4/c1-6-14(2)21-15(3)12-16(4)22(28-21)19-20(25)18(13-24(27-5)23(19)26)17-10-8-7-9-11-17/h7-11,13-16,21-22,25H,6,12H2,1-5H3/t14-,15+,16-,21-,22-/m1/s1
Canonical SMILES:	CC[C@H]([C@H]1O[C@H]([C@@H](C[C@@H]1C)C)c1c(O)c(cn(c1=O)OC)c1ccccc1)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
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota				PMID[20550123]

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Biological Activity

Activity Type	# Activity
IC50	2
MIC	2

Activity Type	# Activity
Organism	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2.79	ug/ml	20058933
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5	ug/ml	16989527
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	2.99	ug/ml	16989527
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5	ug/ml	16441087

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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 NPC103605 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	95
0.1-0.2	560
0.2-0.3	1759
0.3-0.4	4363
0.4-0.5	10697
0.5-0.6	12177
0.6-0.7	1212
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.6438	Remote Similarity	NPC296712
0.6439	Remote Similarity	NPC321670
0.6444	Remote Similarity	NPC321252
0.6444	Remote Similarity	NPC474157
0.6444	Remote Similarity	NPC252544

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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 NPC103605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	396
0.2-0.3	786
0.3-0.4	1579
0.4-0.5	3012
0.5-0.6	2713
0.6-0.7	541
0.7-0.8	33
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
0.6434	Remote Similarity	NPD2233	Approved
0.6439	Remote Similarity	NPD5048	Discontinued
0.6443	Remote Similarity	NPD4453	Approved
0.6443	Remote Similarity	NPD4452	Approved
0.6443	Remote Similarity	NPD4445	Approved

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Structure

NPC103605 OpenBabel07101718292D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 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 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 5 27 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 2 1 6 0 0 0 15 3 1 6 0 0 0 15 21 1 0 0 0 0 16 4 1 6 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 21 14 1 1 0 0 0 21 28 1 0 0 0 0 22 19 1 1 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 26 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	54729474
ChEMBL	CHEMBL1172613
ZINC

Physicochemical Properties

Molecular Weight:	385.23
ALogP:	-1.2553
MLogP:	3.44
XLogP:	6.114
# Rotatable Bonds:	11
Polar Surface Area:	59
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	28

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