NPASS Natural Product

Natural Product: NPC73422

Natural Product ID:	NPC73422
Common Name:	Aglafolin
IUPAC Name:	methyl (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
Synonyms:	Aglafolin; Methyl Rocaglate
Molecular Formula:	C28H28O8
Standard InCHIKey:	VFTGDXPPYSWBSO-GWNOIRNCSA-N
Standard InCHI:	InChI=1S/C28H28O8/c1-32-18-12-10-17(11-13-18)28-23(16-8-6-5-7-9-16)22(26(30)35-4)25(29)27(28,31)24-20(34-3)14-19(33-2)15-21(24)36-28/h5-15,22-23,25,29,31H,1-4H3/t22-,23-,25-,27+,28+/m1/s1
Canonical SMILES:	COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H]([C@@H]([C@H]1c1ccccc1)C(=O)OC)O)c(OC)cc(c3)OC
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
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota	Stems	DOI[10.1016/0014-2999(92)90156-X]
NPO10244	Aglaia elliptifolia	Species	Meliaceae	Eukaryota		PMID[9214732]
NPO13294	Pinus yunnanensis	Species	Pinaceae	Eukaryota		UNPD*
NPO18130.1	Erophaca baetica subsp. baetica	Subspecies	Fabaceae	Eukaryota		UNPD*
NPO18179	Leucopaxillus amarus	Species	Tricholomataceae	Eukaryota		UNPD*
NPO19682	Duguetia chrysocarpa	Species	Annonaceae	Eukaryota		UNPD*
NPO20222	Franseria ambrosioides	NA	NA	NA		UNPD*
NPO20667	Cereus queretaroensis	Species	Sagartiidae	Eukaryota		UNPD*
NPO21152	Senecio asper	Species	Asteraceae	Eukaryota		UNPD*
NPO21632	Chlorobium phaeovibrioides	Species	Chlorobiaceae	Bacteria		UNPD*

Showing 1 to 10 of 23 entries

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Biological Activity

Activity Type	# Activity
EC50	6
ED50	9
IC50	7
MIC	3
Others	8

Activity Type	# Activity
Cell Line	13
Individual Protein	4
Organism	9
Others	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	163	nM	15043407
NPT1091	Cell Line	RPMI-7951	Homo sapiens	IC50	=	0.001	ug/ml	9214732
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	3	ug/ml	10775404
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	8	ug/ml	10775404
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	0.05	ug/ml	10775404
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.012	nM	23301897
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.002	ug/ml	9214732
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	0.005	ug/ml	9214732
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	243	nM	15043407
NPT2	Others	Unspecified		IC50	=	2300	nM	17055270

Showing 1 to 10 of 32 entries

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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 NPC73422 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	268
0.1-0.2	1014
0.2-0.3	2136
0.3-0.4	4058
0.4-0.5	7453
0.5-0.6	5135
0.6-0.7	4044
0.7-0.8	6548
0.8-0.85	213
0.85-0.9	6
0.9-0.95	10
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.8012	Intermediate Similarity	NPC164427
0.8012	Intermediate Similarity	NPC78492
0.8012	Intermediate Similarity	NPC237946
0.8012	Intermediate Similarity	NPC300845
0.8013	Intermediate Similarity	NPC474687

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 NPC73422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	775
0.2-0.3	1595
0.3-0.4	2518
0.4-0.5	2120
0.5-0.6	1205
0.6-0.7	511
0.7-0.8	144
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6833	Remote Similarity	NPD1247	Approved
0.6839	Remote Similarity	NPD1894	Discontinued
0.6848	Remote Similarity	NPD6353	Approved
0.6852	Remote Similarity	NPD4625	Phase 3
0.6854	Remote Similarity	NPD6971	Discontinued

Showing 1 to 5 of 200 entries

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Structure

CID73422 OpenBabel06191715412D 36 40 0 0 1 0 0 0 0 0999 V2000 -3.1451 -3.2489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3645 -1.0662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5474 3.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0111 2.9031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9217 -0.9094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9184 0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1063 -1.3840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0996 0.5030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2875 -0.9151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6726 -1.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2411 -0.5320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9739 -1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5425 -1.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4707 1.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6536 0.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2842 0.0284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3062 -0.3402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9088 -2.1514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4707 0.4820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6536 1.8973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8364 0.4820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6466 1.9097 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6466 0.9662 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8364 1.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8102 2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4604 2.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0133 1.9085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8232 0.4830 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8063 3.3681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1625 3.2825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5074 2.7507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2101 -3.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3645 -0.0341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6536 2.9294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3847 2.1975 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 32 1 0 0 0 0 2 33 1 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 23 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 24 2 0 0 0 0 20 34 1 0 0 0 0 21 24 1 0 0 0 0 21 36 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 1 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 25 27 1 1 0 0 0 25 29 1 0 0 0 0 26 30 2 0 0 0 0 26 35 1 0 0 0 0 27 28 1 6 0 0 0 27 31 1 0 0 0 0 28 17 1 6 0 0 0 28 36 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	393601
ChEMBL	CHEMBL394528
ZINC

Physicochemical Properties

Molecular Weight:	492.18
ALogP:	-2.1147
MLogP:	3.66
XLogP:	5.396
# Rotatable Bonds:	13
Polar Surface Area:	103.68
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	36

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