NPASS Natural Product

Natural Product: NPC161881

Natural Product ID:	NPC161881
Common Name:	Swertisin
IUPAC Name:	5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Synonyms:	Swertisin
Molecular Formula:	C22H22O10
Standard InCHIKey:	ABRULANJVVJLFI-DGHBBABESA-N
Standard InCHI:	InChI=1S/C22H22O10/c1-30-13-7-14-16(11(25)6-12(31-14)9-2-4-10(24)5-3-9)19(27)17(13)22-21(29)20(28)18(26)15(8-23)32-22/h2-7,15,18,20-24,26-29H,8H2,1H3/t15-,18-,20+,21-,22+/m1/s1
Canonical SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(OC)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)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	Reference
NPO11207	Wilbrandia ebracteata	Species	Cucurbitaceae	Eukaryota	Root	PMID[20678557]
NPO12173	Zantedeschia aethiopica	Species	Araceae	Eukaryota		PMID[25924520]
NPO12812	Aleurites moluccanus	Species	Euphorbiaceae	Eukaryota		PMID[21660087]
NPO13056	Lophatherum gracile	Species	Poaceae	Eukaryota		PMID[25527702]
NPO13056	Lophatherum gracile	Species	Poaceae	Eukaryota		TM-MC*
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota		TM-MC*
NPO19122	Ziziphi spinosae semen	NA	NA	NA		TCMSP*
NPO20798	Echinodorus grandiflorus	Species	Alismataceae	Eukaryota	Leaves	PMID[26692456]
NPO21575	Lomatogonium rotatum	Species	Gentianaceae	Eukaryota		PMID[2608753]
NPO27608	Gentianopsis barbata	Species	Gentianaceae	Eukaryota		PMID[2608753]

Showing 1 to 10 of 25 entries

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Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	24.9	%	3379415
NPT2	Others	Unspecified		IC50	=	146500	nM	22867049

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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 NPC161881 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	279
0.1-0.2	1056
0.2-0.3	2184
0.3-0.4	5129
0.4-0.5	7624
0.5-0.6	3135
0.6-0.7	3422
0.7-0.8	4130
0.8-0.85	1521
0.85-0.9	1668
0.9-0.95	661
0.95-1	80

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Similarity Score	Similarity Level	Natural Product ID
0.9329	High Similarity	NPC472421
0.9329	High Similarity	NPC29777
0.9333	High Similarity	NPC256141
0.9333	High Similarity	NPC210597
0.9333	High Similarity	NPC477957

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 NPC161881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	807
0.2-0.3	1517
0.3-0.4	2456
0.4-0.5	2124
0.5-0.6	1187
0.6-0.7	532
0.7-0.8	195
0.8-0.85	23
0.85-0.9	27
0.9-0.95	11
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7197	Intermediate Similarity	NPD4060	Phase 1
0.7202	Intermediate Similarity	NPD7801	Approved
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7208	Intermediate Similarity	NPD2861	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID161881 OpenBabel06191715532D 32 35 0 0 1 0 0 0 0 0999 V2000 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -2.5981 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 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 -7.7942 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 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 -1.7321 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 -0.5000 0.0000 C 0 0 2 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -2.5981 -1.5000 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 -1.7321 -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 -4.3301 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 30 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 9 12 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 25 2 0 0 0 0 12 31 1 0 0 0 0 13 17 1 0 0 0 0 13 30 1 0 0 0 0 14 16 2 0 0 0 0 14 31 1 0 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 15 32 1 0 0 0 0 16 19 1 0 0 0 0 17 19 2 0 0 0 0 18 20 1 0 0 0 0 18 26 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 17 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	124034
ChEMBL	CHEMBL486415
ZINC

Physicochemical Properties

Molecular Weight:	446.12
ALogP:	-3.7117
MLogP:	2.78
XLogP:	0.011
# Rotatable Bonds:	11
Polar Surface Area:	166.14
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	32

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