NPASS Natural Product

Natural Product: NPC4390

Natural Product ID:	NPC4390
Common Name:	Methyl (2S,3S,4S,5R,6S)-6-[5-(5,7-Dihydroxy-4-Oxochromen-2-Yl)-2-Hydroxyphenoxy]-3,4,5-Trihydroxyoxane-2-Carboxylate
IUPAC Name:	methyl (2S,3S,4S,5R,6S)-6-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylate
Synonyms:
Molecular Formula:	C22H20O12
Standard InCHIKey:	YJPDUFUDVOEGKU-SXFAUFNYSA-N
Standard InCHI:	InChI=1S/C22H20O12/c1-31-21(30)20-18(28)17(27)19(29)22(34-20)33-14-4-8(2-3-10(14)24)13-7-12(26)16-11(25)5-9(23)6-15(16)32-13/h2-7,17-20,22-25,27-29H,1H3/t17-,18-,19+,20-,22+/m0/s1
Canonical SMILES:	COC(=O)[C@H]1O[C@@H](Oc2cc(ccc2O)c2cc(=O)c3c(o2)cc(cc3O)O)[C@@H]([C@H]([C@@H]1O)O)O
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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota				PMID[17027268]

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Biological Activity

Activity Type	# Activity
MIC	11

Activity Type	# Activity
Organism	11

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1155	Organism	Sporothrix schenckii	Sporothrix schenckii	MIC	>	50	ug/ml	9873651
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50	ug/ml	25089583
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	50	ug/ml	16472241
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	50	ug/ml	20576577
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50	ug/ml	17988097
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	50	ug/ml	26476666
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50	ug/ml	19743809
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50	ug/ml	25089583
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	=	6.25	ug/ml	25871261
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	6.25	ug/ml	16472241

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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 NPC4390 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	310
0.1-0.2	1246
0.2-0.3	2714
0.3-0.4	5733
0.4-0.5	6573
0.5-0.6	3479
0.6-0.7	3303
0.7-0.8	4348
0.8-0.85	1613
0.85-0.9	1001
0.9-0.95	381
0.95-1	188

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Similarity Score	Similarity Level	Natural Product ID
0.9458	High Similarity	NPC294629
0.9461	High Similarity	NPC89052
0.9461	High Similarity	NPC476773
0.9461	High Similarity	NPC251417
0.9464	High Similarity	NPC473071

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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 NPC4390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	860
0.2-0.3	1871
0.3-0.4	2587
0.4-0.5	1882
0.5-0.6	1026
0.6-0.7	418
0.7-0.8	140
0.8-0.85	26
0.85-0.9	12
0.9-0.95	10
0.95-1	3

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6951	Remote Similarity	NPD3225	Approved
0.6957	Remote Similarity	NPD7930	Approved
0.6964	Remote Similarity	NPD4062	Phase 3
0.697	Remote Similarity	NPD2798	Approved
0.697	Remote Similarity	NPD4420	Approved

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Structure

NPC4390 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 -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 -6.0622 0.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 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 -6.0622 1.5000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 1.7321 -1.0000 0.0000 C 0 0 1 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 1.7321 0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 31 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 24 1 0 0 0 0 11 16 2 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 26 2 0 0 0 0 13 32 1 0 0 0 0 14 33 1 0 0 0 0 15 16 1 0 0 0 0 15 32 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 1 0 0 0 18 20 1 0 0 0 0 18 28 1 6 0 0 0 19 22 1 0 0 0 0 19 29 1 6 0 0 0 20 21 1 1 0 0 0 20 34 1 0 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 22 33 1 1 0 0 0 22 34 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44439687
ChEMBL	CHEMBL239349
ZINC

Physicochemical Properties

Molecular Weight:	476.10
ALogP:	-3.7385
MLogP:	2.56
XLogP:	-0.026
# Rotatable Bonds:	12
Polar Surface Area:	192.44
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	34

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