NPASS Natural Product

Natural Product: NPC329743

Natural Product ID:	NPC329743
Common Name:	1-O-Acetylmethyl Rocaglate
IUPAC Name:	(1R,2R,3S,3aR,8bS)-1-acetyloxy-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylic acid
Synonyms:	1-O-Acetylmethyl Rocaglate
Molecular Formula:	C29H28O9
Standard InCHIKey:	XGFHSPORRWHGPC-IDAMAFBJSA-N
Standard InCHI:	InChI=1S/C29H28O9/c1-16(30)37-26-23(27(31)32)24(17-8-6-5-7-9-17)29(18-10-12-19(34-2)13-11-18)28(26,33)25-21(36-4)14-20(35-3)15-22(25)38-29/h5-15,23-24,26,33H,1-4H3,(H,31,32)/t23-,24-,26-,28+,29+/m1/s1
Canonical SMILES:	COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H]([C@@H]([C@H]1c1ccccc1)C(=O)O)OC(=O)C)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	Collection Location	Collection Time	Reference
NPO3427	Aglaia rubiginosa	Species	Meliaceae	Eukaryota	twigs and leaves			PMID[15043407]

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Biological Activity

Activity Type	# Activity
ED50	6

Activity Type	# Activity
Cell Line	5
Others	1

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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	=	112	nM	1294693
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	149	nM	19228038
NPT2	Others	Unspecified		ED50	=	206	nM	21546253
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	205	nM	12880316
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	224	nM	17877337
NPT91	Cell Line	KB	Homo sapiens	ED50	=	168	nM	10.6019/CHEMBL1201861

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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 NPC329743 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	272
0.1-0.2	1040
0.2-0.3	2111
0.3-0.4	4196
0.4-0.5	7571
0.5-0.6	4842
0.6-0.7	4087
0.7-0.8	6547
0.8-0.85	204
0.85-0.9	5
0.9-0.95	10
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.8012	Intermediate Similarity	NPC19947
0.8012	Intermediate Similarity	NPC271741
0.8012	Intermediate Similarity	NPC207584
0.8012	Intermediate Similarity	NPC43638
0.8024	Intermediate Similarity	NPC24164

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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 NPC329743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	782
0.2-0.3	1580
0.3-0.4	2510
0.4-0.5	2122
0.5-0.6	1221
0.6-0.7	503
0.7-0.8	149
0.8-0.85	10
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
0.6852	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1203	Approved
0.6865	Remote Similarity	NPD7549	Discontinued
0.6867	Remote Similarity	NPD4477	Approved

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Structure

NPC329743 OpenBabel07101718282D 38 42 0 0 1 0 0 0 0 0999 V2000 1.2495 2.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3120 -3.0501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0312 0.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4498 3.9343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8370 -2.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -2.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9325 -1.2912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2643 -2.0339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1938 -0.7545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9814 0.0954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7020 -0.8341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 -0.6432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2387 -1.5728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4498 1.1952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6591 -0.1744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 3.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3597 -1.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0733 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1467 -1.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4498 0.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6591 1.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8684 0.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4050 1.9339 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4050 1.0208 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8684 1.1952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5367 2.2160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1437 2.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.4773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5367 0.7387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9207 4.1425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9778 2.0992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0483 3.3786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5367 2.2160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6834 -2.2160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2405 -0.1744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6591 3.4778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2545 3.0844 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 16 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 36 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 17 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 30 2 0 0 0 0 16 37 1 0 0 0 0 17 24 1 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 25 2 0 0 0 0 21 36 1 0 0 0 0 22 25 1 0 0 0 0 22 38 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 23 27 1 1 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 26 28 1 1 0 0 0 26 37 1 0 0 0 0 27 31 2 0 0 0 0 27 32 1 0 0 0 0 28 29 1 6 0 0 0 28 33 1 0 0 0 0 29 18 1 6 0 0 0 29 38 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44575584
ChEMBL	CHEMBL517992
ZINC

Physicochemical Properties

Molecular Weight:	520.17
ALogP:	-1.9866
MLogP:	3.66
XLogP:	4.957
# Rotatable Bonds:	14
Polar Surface Area:	120.75
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	38

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