NPASS Natural Product

Natural Product: NPC199079

Natural Product ID:	NPC199079
Common Name:	(2S)-5,7,5'-Trihydroxyflavanone 2'-O-Beta-D-Glucopyranosyl-(1->3)-Alpha-L-2-O-Acetylrhamnopyanoside
IUPAC Name:	[(2S,3R,4R,5S,6S)-2-[2-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-hydroxyphenoxy]-5-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl] acetate
Synonyms:
Molecular Formula:	C29H34O16
Standard InCHIKey:	QLBVBCPJNCEFDN-QLAWMWOCSA-N
Standard InCHI:	InChI=1S/C29H34O16/c1-10-22(36)26(45-28-25(39)24(38)23(37)20(9-30)44-28)27(41-11(2)31)29(40-10)43-17-4-3-12(32)5-14(17)18-8-16(35)21-15(34)6-13(33)7-19(21)42-18/h3-7,10,18,20,22-30,32-34,36-39H,8-9H2,1-2H3/t10-,18-,20+,22-,23+,24-,25+,26+,27+,28-,29-/m0/s1
Canonical SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC(=O)C)[C@@H](O[C@H]([C@@H]2O)C)Oc2ccc(cc2[C@@H]2CC(=O)c3c(O2)cc(cc3O)O)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
NPO26960	Cyclosorus acuminatus	Species	Thelypteridaceae	Eukaryota	Rhizomes			PMID[17125239]

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Biological Activity

Activity Type	# Activity
MIC	4

Activity Type	# Activity
Organism	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	32	ug/ml	20655237
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	32	ug/ml	20576577
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128	ug/ml	20655237
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64	ug/ml	20655237

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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 NPC199079 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	299
0.1-0.2	1194
0.2-0.3	2422
0.3-0.4	5291
0.4-0.5	6709
0.5-0.6	4057
0.6-0.7	3608
0.7-0.8	4371
0.8-0.85	1908
0.85-0.9	649
0.9-0.95	373
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC271479
0.9136	High Similarity	NPC136761
0.9136	High Similarity	NPC328093
0.9136	High Similarity	NPC472320
0.9141	High Similarity	NPC244875

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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 NPC199079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	864
0.2-0.3	1692
0.3-0.4	2597
0.4-0.5	1967
0.5-0.6	1127
0.6-0.7	404
0.7-0.8	145
0.8-0.85	31
0.85-0.9	9
0.9-0.95	8
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6933	Remote Similarity	NPD3225	Approved
0.6941	Remote Similarity	NPD4308	Phase 3
0.6941	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1610	Phase 2
0.6957	Remote Similarity	NPD422	Phase 1

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Structure

NPC199079 OpenBabel07101718182D 45 49 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 -1.7321 4.0000 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 -5.1962 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 4.3301 -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 1 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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 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 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 1 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 1.7321 1.0000 0.0000 C 0 0 2 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 3.4641 1.0000 0.0000 C 0 0 1 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 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 3.4641 0.0000 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 2 11 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 17 1 0 0 0 0 5 12 2 0 0 0 0 5 14 1 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 13 1 0 0 0 0 7 19 2 0 0 0 0 8 16 1 0 0 0 0 8 18 1 0 0 0 0 9 30 1 0 0 0 0 10 1 1 6 0 0 0 10 22 1 0 0 0 0 10 40 1 0 0 0 0 11 31 2 0 0 0 0 11 41 1 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 17 2 0 0 0 0 15 21 2 0 0 0 0 15 34 1 0 0 0 0 16 21 1 0 0 0 0 16 35 2 0 0 0 0 17 43 1 0 0 0 0 18 14 1 6 0 0 0 18 42 1 0 0 0 0 19 21 1 0 0 0 0 19 42 1 0 0 0 0 20 9 1 1 0 0 0 20 23 1 0 0 0 0 20 44 1 0 0 0 0 22 26 1 0 0 0 0 22 36 1 1 0 0 0 23 24 1 0 0 0 0 23 37 1 6 0 0 0 24 25 1 0 0 0 0 24 38 1 1 0 0 0 25 28 1 0 0 0 0 25 39 1 6 0 0 0 26 27 1 0 0 0 0 26 45 1 6 0 0 0 27 29 1 0 0 0 0 27 41 1 6 0 0 0 28 44 1 0 0 0 0 28 45 1 1 0 0 0 29 40 1 0 0 0 0 29 43 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	11995072
ChEMBL	CHEMBL506566
ZINC

Physicochemical Properties

Molecular Weight:	638.18
ALogP:	-4.8894
MLogP:	2.89
XLogP:	-1.697
# Rotatable Bonds:	18
Polar Surface Area:	251.36
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	45

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