NPASS Natural Product

Natural Product: NPC321478

Natural Product ID:	NPC321478
Common Name:	Paeonoside Decaacetate
IUPAC Name:	[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxo-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxychromen-7-yl]oxyoxan-2-yl]methyl acetate
Synonyms:	Paeonoside Decaacetate
Molecular Formula:	C47H50O26
Standard InCHIKey:	NLVNWKWBXDAKIC-GHNQEIAISA-N
Standard InCHI:	InChI=1S/C47H50O26/c1-19(48)59-17-34-39(63-23(5)52)42(65-25(7)54)44(67-27(9)56)46(71-34)69-31-15-32(62-22(4)51)36-33(16-31)70-38(29-11-13-30(14-12-29)61-21(3)50)41(37(36)58)73-47-45(68-28(10)57)43(66-26(8)55)40(64-24(6)53)35(72-47)18-60-20(2)49/h11-16,34-35,39-40,42-47H,17-18H2,1-10H3/t34-,35-,39-,40-,42+,43+,44-,45-,46-,47+/m1/s1
Canonical SMILES:	CC(=O)OC[C@H]1O[C@@H](Oc2cc(OC(=O)C)c3c(c2)oc(c(c3=O)O[C@@H]2O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]2OC(=O)C)OC(=O)C)OC(=O)C)c2ccc(cc2)OC(=O)C)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
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
NPO31221	Delphinium staphisagria	Species	Ranunculaceae	Eukaryota	Aerial parts			PMID[21466157]

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Biological Activity

Activity Type	# Activity
IC50	2
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1000000	nM	21466157
NPT2	Others	Unspecified		Ratio IC50	=	58.1		21466157
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	17200	nM	21466157
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Inhibition	=	82	%	21466157
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	85	%	21466157
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	23	%	21466157

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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 NPC321478 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	345
0.1-0.2	1258
0.2-0.3	2916
0.3-0.4	6244
0.4-0.5	6640
0.5-0.6	3589
0.6-0.7	4519
0.7-0.8	4167
0.8-0.85	783
0.85-0.9	321
0.9-0.95	104
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8817	High Similarity	NPC470447
0.8817	High Similarity	NPC470446
0.8817	High Similarity	NPC470445
0.8817	High Similarity	NPC470718
0.8817	High Similarity	NPC470449

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 NPC321478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	900
0.2-0.3	1740
0.3-0.4	2705
0.4-0.5	1985
0.5-0.6	1024
0.6-0.7	313
0.7-0.8	129
0.8-0.85	15
0.85-0.9	12
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6751	Remote Similarity	NPD5005	Approved
0.6751	Remote Similarity	NPD5006	Approved
0.6752	Remote Similarity	NPD17	Approved
0.6758	Remote Similarity	NPD5242	Approved
0.6761	Remote Similarity	NPD6386	Approved

Showing 1 to 5 of 200 entries

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Structure

CID321478 OpenBabel06191716152D 73 77 0 0 1 0 0 0 0 0999 V2000 5.9845 4.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5648 -2.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 6.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 -1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5492 2.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 -2.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6943 0.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2746 -1.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4197 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4197 1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8549 4.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7098 2.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7098 4.9359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 3.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4197 1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5648 3.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6943 3.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 -1.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8394 4.9359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 -2.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4197 5.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 -0.9872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5492 1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7098 -2.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8394 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4197 -0.9872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2746 0.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 1.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8549 3.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 4.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4197 2.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5648 1.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 2.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8394 2.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7098 1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 1.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8394 1.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8549 -1.4808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9845 1.4808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7098 -0.9872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1295 1.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7098 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1295 2.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8549 0.4936 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8394 5.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 -3.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2746 6.4167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 -0.4936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4041 1.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7098 -3.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8394 -0.9872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4197 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1295 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7098 1.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 0.4936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6943 4.4423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 -2.4679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4197 4.9359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5648 -0.4936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6943 1.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8549 -2.4679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9845 0.4936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 -1.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2746 1.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 0.4936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2746 3.4551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 3.4551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9845 3.4551 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 -0.8549 1.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 13 1 0 0 0 0 11 29 2 0 0 0 0 12 14 2 0 0 0 0 12 29 1 0 0 0 0 13 30 2 0 0 0 0 14 30 1 0 0 0 0 15 31 2 0 0 0 0 15 32 1 0 0 0 0 16 31 1 0 0 0 0 16 33 2 0 0 0 0 17 59 1 0 0 0 0 18 60 1 0 0 0 0 19 48 2 0 0 0 0 19 59 1 0 0 0 0 20 49 2 0 0 0 0 20 60 1 0 0 0 0 21 50 2 0 0 0 0 21 61 1 0 0 0 0 22 51 2 0 0 0 0 22 62 1 0 0 0 0 23 52 2 0 0 0 0 23 63 1 0 0 0 0 24 53 2 0 0 0 0 24 64 1 0 0 0 0 25 54 2 0 0 0 0 25 65 1 0 0 0 0 26 55 2 0 0 0 0 26 66 1 0 0 0 0 27 56 2 0 0 0 0 27 67 1 0 0 0 0 28 57 2 0 0 0 0 28 68 1 0 0 0 0 29 38 1 0 0 0 0 30 61 1 0 0 0 0 31 69 1 0 0 0 0 32 36 2 0 0 0 0 32 62 1 0 0 0 0 33 36 1 0 0 0 0 33 70 1 0 0 0 0 34 17 1 6 0 0 0 34 39 1 0 0 0 0 34 71 1 0 0 0 0 35 18 1 6 0 0 0 35 40 1 0 0 0 0 35 72 1 0 0 0 0 36 37 1 0 0 0 0 37 41 1 0 0 0 0 37 58 2 0 0 0 0 38 41 2 0 0 0 0 38 70 1 0 0 0 0 39 42 1 0 0 0 0 39 63 1 1 0 0 0 40 43 1 0 0 0 0 40 64 1 1 0 0 0 41 73 1 0 0 0 0 42 44 1 0 0 0 0 42 65 1 6 0 0 0 43 45 1 0 0 0 0 43 66 1 6 0 0 0 44 46 1 0 0 0 0 44 67 1 1 0 0 0 45 47 1 0 0 0 0 45 68 1 1 0 0 0 46 69 1 6 0 0 0 46 71 1 0 0 0 0 47 72 1 0 0 0 0 47 73 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	52952637
ChEMBL	CHEMBL1774170
ZINC

Physicochemical Properties

Molecular Weight:	1030.26
ALogP:	-2.3877
MLogP:	3.77
XLogP:	3.898
# Rotatable Bonds:	37
Polar Surface Area:	326.22
# H-Bond Aceptor:	22
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	73

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