NPASS Natural Product

Natural Product: NPC235051

Natural Product ID:	NPC235051
Common Name:	Patrinioside
IUPAC Name:	[(1S,2S,3R,4S)-2-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-methyl-3-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]cyclopentyl] 3-methylbutanoate
Synonyms:	Patrinioside
Molecular Formula:	C21H36O10
Standard InCHIKey:	HRAKXIGVAPGHEW-XHHYMNQSSA-N
Standard InCHI:	InChI=1S/C21H36O10/c1-10(2)5-16(24)31-15-6-12(11(3)7-22)13(21(15,4)28)9-29-20-19(27)18(26)17(25)14(8-23)30-20/h10,12-15,17-20,22-23,25-28H,3,5-9H2,1-2,4H3/t12-,13+,14-,15+,17-,18+,19-,20-,21+/m1/s1
Canonical SMILES:	OC[C@H]1O[C@@H](OC[C@H]2[C@H](C[C@@H]([C@@]2(C)O)OC(=O)CC(C)C)C(=C)CO)[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
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots			PMID[23002924]

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000	nM	22194678
NPT2	Others	Unspecified		IC50	=	23800	nM	20439609

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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 NPC235051 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	122
0.1-0.2	1105
0.2-0.3	3853
0.3-0.4	9697
0.4-0.5	6839
0.5-0.6	5029
0.6-0.7	3613
0.7-0.8	584
0.8-0.85	27
0.85-0.9	17
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7364	Intermediate Similarity	NPC277583
0.7368	Intermediate Similarity	NPC322922
0.7368	Intermediate Similarity	NPC321812
0.7374	Intermediate Similarity	NPC39453
0.7374	Intermediate Similarity	NPC96736

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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 NPC235051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	2028
0.2-0.3	4004
0.3-0.4	1994
0.4-0.5	551
0.5-0.6	326
0.6-0.7	110
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5748	Remote Similarity	NPD6336	Discontinued
0.5755	Remote Similarity	NPD7625	Phase 1
0.5758	Remote Similarity	NPD6925	Approved
0.5758	Remote Similarity	NPD5776	Phase 2
0.5763	Remote Similarity	NPD4634	Approved

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Structure

NPC235051 OpenBabel07101719402D 31 32 0 0 1 0 0 0 0 0999 V2000 -7.6236 0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0249 -0.0817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8744 1.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -1.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4426 -0.7862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0334 2.6418 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0303 0.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8255 1.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 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 -5.0468 0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4480 -0.6817 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 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 2 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2903 3.3109 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 -5.8603 -1.4907 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 -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 -4.0686 -1.3578 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0413 0.2319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 5 10 1 0 0 0 0 5 16 1 0 0 0 0 6 12 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 13 1 0 0 0 0 9 29 1 0 0 0 0 12 11 1 6 0 0 0 12 13 1 0 0 0 0 13 21 1 6 0 0 0 14 8 1 6 0 0 0 14 17 1 0 0 0 0 14 30 1 0 0 0 0 15 21 1 1 0 0 0 15 31 1 0 0 0 0 16 24 2 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 29 1 6 0 0 0 20 30 1 0 0 0 0 21 4 1 1 0 0 0 21 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	71461980
ChEMBL	CHEMBL2152449
ZINC

Physicochemical Properties

Molecular Weight:	448.23
ALogP:	-2.0567
MLogP:	2.67
XLogP:	-0.627
# Rotatable Bonds:	19
Polar Surface Area:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	31

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