NPASS Natural Product

Natural Product: NPC176740

Natural Product ID:	NPC176740
Common Name:	Rutin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms:	NSC-115918; Rutin; Rutoside
Molecular Formula:	C27H30O16
Standard InCHIKey:	IKGXIBQEEMLURG-NVPNHPEKSA-N
Standard InCHI:	InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
Canonical SMILES:	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)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	Reference
NPO10011	Myrsine capitellata	Species	Primulaceae	Eukaryota	UNPD*
NPO10012	Triaenophora rupestris	Species	Orobanchaceae	Eukaryota	UNPD*
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	UNPD*
NPO10029	Prunus dulcis	Species	Rosaceae	Eukaryota	UNPD*
NPO10048	Pyrus bourgaeana	Species	Rosaceae	Eukaryota	UNPD*
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	TM-MC*
NPO10084	Equisetum hyemale	Species	Equisetaceae	Eukaryota	TM-MC*
NPO10098	Glycosmis pseudoracemosa	Species	Rutaceae	Eukaryota	UNPD*
NPO10128	Aplysia punctata	Species	Aplysiidae	Eukaryota	UNPD*
NPO10165	Haematomma porphyrium	Species	Haematommataceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
AC50	1
EC50	6
ED50	1
IC50	64
Ki	6
Others	129
Potency	31

Activity Type	# Activity
Cell Line	30
Individual Protein	54
Organism	40
Others	108
Protein Family	3
Tissue	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC25	=	12.2	nM	17166721
NPT1	Others	Radical scavenging activity		EC50	=	4.8	ug	12502312
NPT1	Others	Radical scavenging activity		IC50	=	12340	nM	14575443
NPT1	Others	Radical scavenging activity		IC50	=	12300	nM	15568781
NPT1	Others	Radical scavenging activity		EC50	=	15.5	ug	21821414
NPT1	Others	Radical scavenging activity		IC50	=	1.83	ug/ml	10.1007/s00044-009-9217-5
NPT1	Others	Radical scavenging activity		IC50	=	38700	nM	23356964
NPT1	Others	Radical scavenging activity		IC50	=	4700	nM	23691929
NPT1	Others	Radical scavenging activity		IC50	=	4700	nM	24387661
NPT1032	Individual Protein	Neuraminidase	Influenza A virus (strain A/USSR/90/1977 H1N1)	IC50	=	95900	nM	25096296

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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 NPC176740 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	332
0.1-0.2	1265
0.2-0.3	2769
0.3-0.4	6301
0.4-0.5	6187
0.5-0.6	3332
0.6-0.7	3598
0.7-0.8	4269
0.8-0.85	1489
0.85-0.9	794
0.9-0.95	351
0.95-1	202

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Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC181465
0.95	High Similarity	NPC116458
0.95	High Similarity	NPC215710
0.95	High Similarity	NPC170052
0.95	High Similarity	NPC265885

Showing 1 to 5 of 200 entries

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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 NPC176740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	868
0.2-0.3	1844
0.3-0.4	2666
0.4-0.5	1865
0.5-0.6	1012
0.6-0.7	398
0.7-0.8	129
0.8-0.85	19
0.85-0.9	9
0.9-0.95	8
0.95-1	5

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6802	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4062	Phase 3
0.681	Remote Similarity	NPD1610	Phase 2
0.681	Remote Similarity	NPD422	Phase 1
0.6827	Remote Similarity	NPD7930	Approved

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Structure

CID176740 OpenBabel06191715552D 43 47 0 0 1 0 0 0 0 0999 V2000 3.4641 4.0000 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 -4.3301 -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 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 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 -3.4641 1.0000 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 -5.1962 0.0000 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 0.0000 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 -0.5000 0.0000 C 0 0 2 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 4.3301 2.5000 0.0000 C 0 0 1 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 -0.8660 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 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 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 -0.8660 5.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 5.1962 1.0000 0.0000 O 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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 2.5981 2.5000 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 -0.0000 -0.0000 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 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 39 1 0 0 0 0 8 1 1 1 0 0 0 8 17 1 0 0 0 0 8 40 1 0 0 0 0 9 24 1 0 0 0 0 10 28 1 0 0 0 0 11 12 2 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 16 2 0 0 0 0 13 31 1 0 0 0 0 14 16 1 0 0 0 0 14 41 1 0 0 0 0 15 7 1 6 0 0 0 15 18 1 0 0 0 0 15 42 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 32 1 6 0 0 0 18 21 1 0 0 0 0 18 33 1 1 0 0 0 19 25 1 0 0 0 0 19 34 2 0 0 0 0 20 22 1 0 0 0 0 20 35 1 1 0 0 0 21 23 1 0 0 0 0 21 36 1 6 0 0 0 22 26 1 0 0 0 0 22 37 1 1 0 0 0 23 27 1 0 0 0 0 23 38 1 1 0 0 0 24 25 2 0 0 0 0 24 41 1 0 0 0 0 25 43 1 0 0 0 0 26 39 1 6 0 0 0 26 40 1 0 0 0 0 27 42 1 0 0 0 0 27 43 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	5280805
ChEMBL	CHEMBL226335
ZINC

Physicochemical Properties

Molecular Weight:	610.15
ALogP:	-6.139
MLogP:	2.67
XLogP:	-1.188
# Rotatable Bonds:	17
Polar Surface Area:	265.52
# H-Bond Aceptor:	11
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	43

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