NPASS Natural Product

Natural Product: NPC243891

Natural Product ID:	NPC243891
Common Name:	Agastenol
IUPAC Name:	[(2R,3S,4E)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]oxolan-3-yl]methyl 4-hydroxybenzoate
Synonyms:	agastenol
Molecular Formula:	C27H26O8
Standard InCHIKey:	NYOJCGUMMQIVQV-HPMYTTEASA-N
Standard InCHI:	InChI=1S/C27H26O8/c1-32-24-12-16(3-9-22(24)29)11-19-14-34-26(18-6-10-23(30)25(13-18)33-2)21(19)15-35-27(31)17-4-7-20(28)8-5-17/h3-13,21,26,28-30H,14-15H2,1-2H3/b19-11-/t21-,26+/m1/s1
Canonical SMILES:	COc1cc(ccc1O)[C@@H]1OC/C(=C/c2ccc(c(c2)OC)O)/[C@H]1COC(=O)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	Collection Location	Collection Time	Reference
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota				PMID[11908994]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	11.4	ug/ml	DrugMatrix in vivo data: Biochemistry

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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 NPC243891 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	234
0.1-0.2	962
0.2-0.3	1985
0.3-0.4	4325
0.4-0.5	7501
0.5-0.6	3841
0.6-0.7	3477
0.7-0.8	6558
0.8-0.85	1738
0.85-0.9	250
0.9-0.95	17
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC118162
0.8571	High Similarity	NPC32079
0.8571	High Similarity	NPC126206
0.8571	High Similarity	NPC83049
0.8571	High Similarity	NPC200726

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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 NPC243891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	754
0.2-0.3	1446
0.3-0.4	2287
0.4-0.5	2244
0.5-0.6	1284
0.6-0.7	684
0.7-0.8	179
0.8-0.85	31
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.703	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1243	Approved
0.7039	Intermediate Similarity	NPD7549	Discontinued
0.7043	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3751	Discontinued

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Structure

NPC243891 OpenBabel07101719512D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.3729 -4.6634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1582 -1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7816 -4.0778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2464 -2.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7327 -3.7688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1974 -2.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1527 -1.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9771 -3.5408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5704 -2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0385 -3.4087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9406 -2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5594 -2.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9716 -3.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0874 -3.7177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8916 -2.4816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5540 -2.9408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8795 -4.6958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3784 -4.5589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 2.5933 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 1.3443 -3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 9 2 0 0 0 0 3 16 1 0 0 0 0 4 7 1 0 0 0 0 4 17 2 0 0 0 0 5 8 2 0 0 0 0 5 17 1 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 20 2 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 11 19 2 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 34 1 0 0 0 0 15 35 1 0 0 0 0 17 27 1 0 0 0 0 19 21 1 0 0 0 0 20 28 1 0 0 0 0 21 15 1 6 0 0 0 21 26 1 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 23 25 2 0 0 0 0 23 30 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 18 1 1 0 0 0 26 34 1 0 0 0 0 27 31 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10073783
ChEMBL	CHEMBL464349
ZINC

Physicochemical Properties

Molecular Weight:	478.16
ALogP:	-1.7908
MLogP:	3.55
XLogP:	3.081
# Rotatable Bonds:	13
Polar Surface Area:	114.68
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	35

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