NPASS Natural Product

Natural Product: NPC130730

Natural Product ID:	NPC130730
Common Name:	Picroside Ii
IUPAC Name:	[(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-6-yl] 4-hydroxy-3-methoxybenzoate
Synonyms:	Picroside II
Molecular Formula:	C23H28O13
Standard InCHIKey:	AKNILCMFRRDTEY-NUGKWEEESA-N
Standard InCHI:	InChI=1S/C23H28O13/c1-31-12-6-9(2-3-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3/t10-,13-,14-,15-,16+,17-,18+,19+,21+,22+,23-/m1/s1
Canonical SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3OC(=O)c2ccc(c(c2)OC)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	Reference
NPO10092	Hesperocyparis bakeri	Species	Cupressaceae	Eukaryota	UNPD*
NPO10102	Pithecellobium albicans	Species	Fabaceae	Eukaryota	UNPD*
NPO10553	Heterophyllaea pustulata	Species	Rubiaceae	Eukaryota	UNPD*
NPO11255	Veronica thomsonii	Species	Plantaginaceae	Eukaryota	UNPD*
NPO11397	Cladophora rupestris	Species	Cladophoraceae	Eukaryota	UNPD*
NPO11491	Vellozia declinans	Species	Velloziaceae	Eukaryota	UNPD*
NPO1150	Juncus effusus	Species	Juncaceae	Eukaryota	UNPD*
NPO11674	Viburnum lantanoides	Species	Adoxaceae	Eukaryota	UNPD*
NPO12047	Solanum unguiculatum	Species	Solanaceae	Eukaryota	UNPD*
NPO12175	Iostephane heterophylla	Species	Asteraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
n.a.	1
Others	9

Activity Type	# Activity
Cell Line	6
Organism	3
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	6.0 � 0.01	�M	28787158
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	103	%	6677713
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	101	%	6677713
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	78	%	6677713
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	27	IU/L	6677713
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	28	IU/L	6677713
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	40	IU/L	6677713
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	31.6	%	19904996
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	59.4	%	19904996
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	46	%	10395515

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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 NPC130730 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	286
0.1-0.2	1103
0.2-0.3	2363
0.3-0.4	5011
0.4-0.5	7022
0.5-0.6	4667
0.6-0.7	5652
0.7-0.8	4404
0.8-0.85	295
0.85-0.9	65
0.9-0.95	16
0.95-1	5

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Similarity Score	Similarity Level	Natural Product ID
0.8155	Intermediate Similarity	NPC223335
0.816	Intermediate Similarity	NPC98009
0.8161	Intermediate Similarity	NPC5786
0.8161	Intermediate Similarity	NPC235575
0.8161	Intermediate Similarity	NPC254540

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 NPC130730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	825
0.2-0.3	1813
0.3-0.4	2671
0.4-0.5	2003
0.5-0.6	1077
0.6-0.7	407
0.7-0.8	69
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6537	Remote Similarity	NPD7584	Approved
0.6543	Remote Similarity	NPD17	Approved
0.6545	Remote Similarity	NPD1876	Approved
0.655	Remote Similarity	NPD7699	Phase 2
0.655	Remote Similarity	NPD4420	Approved

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Structure

CID130730 OpenBabel06191715492D 36 40 0 0 1 0 0 0 0 0999 V2000 -6.1943 3.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2891 0.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2672 0.8600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9290 2.3463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4062 0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6199 1.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2514 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5762 1.8111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9071 2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9448 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6146 1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9448 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0787 3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6418 1.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6768 2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9349 0.0982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5544 2.0190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8108 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 4.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3328 0.2363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2161 3.5053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9727 1.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3467 1.8917 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 9 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 5 32 1 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 20 1 0 0 0 0 10 4 1 6 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 26 1 0 0 0 0 12 31 1 0 0 0 0 13 7 1 1 0 0 0 13 15 1 0 0 0 0 13 33 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 6 0 0 0 15 16 1 0 0 0 0 15 27 1 6 0 0 0 16 17 1 0 0 0 0 16 28 1 1 0 0 0 17 22 1 0 0 0 0 17 29 1 6 0 0 0 18 19 1 0 0 0 0 18 34 1 1 0 0 0 19 23 1 6 0 0 0 19 36 1 0 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 32 1 0 0 0 0 21 35 1 1 0 0 0 22 33 1 0 0 0 0 22 35 1 1 0 0 0 23 8 1 6 0 0 0 23 36 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11944602
ChEMBL	CHEMBL510404
ZINC

Physicochemical Properties

Molecular Weight:	512.15
ALogP:	-4.4862
MLogP:	2.56
XLogP:	-1.261
# Rotatable Bonds:	15
Polar Surface Area:	197.13
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	36

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