NPASS Natural Product

Natural Product: NPC262253

Natural Product ID:	NPC262253
Common Name:	Combretastatin A4
IUPAC Name:	2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
Synonyms:	Combrestatin A4; NSC-613729
Molecular Formula:	C18H20O5
Standard InCHIKey:	HVXBOLULGPECHP-WAYWQWQTSA-N
Standard InCHI:	InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
Canonical SMILES:	COc1cc(/C=Cc2ccc(c(c2)O)OC)cc(c1OC)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	TCM_Taiwan*
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota	PMID[19228038]
NPO33339	combretum erythrophyllum	Species	Combretaceae	Eukaryota	PMID[10785413]

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Biological Activity

Activity Type	# Activity
EC50	22
ED50	20
GI50	499
IC50	923
Kd	1
Ki	3
MIC	4
Others	568

Activity Type	# Activity
Cell Line	1338
Individual Protein	40
Organism	42
Others	426
Protein Complex	105
Protein Family	89

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	14.1	nM	25466200
NPT1045	Cell Line	U2OS	Homo sapiens	Activity	=	30	%	25466200
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	3.9	ug/ml	10212132
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.39	ug/ml	10893310
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.39	ug/ml	12036362
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	>	0.1	ug/ml	15943482
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	390	nM	18303849
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.39	ug/ml	16252907
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.39	ug/ml	19228038
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.39	ug/ml	19709889

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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 NPC262253 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	232
0.1-0.2	1256
0.2-0.3	3304
0.3-0.4	9444
0.4-0.5	3389
0.5-0.6	2880
0.6-0.7	5050
0.7-0.8	4025
0.8-0.85	691
0.85-0.9	456
0.9-0.95	105
0.95-1	57

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Similarity Score	Similarity Level	Natural Product ID
0.8952	High Similarity	NPC118533
0.8952	High Similarity	NPC242032
0.8952	High Similarity	NPC165045
0.8952	High Similarity	NPC319625
0.8952	High Similarity	NPC163332

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 NPC262253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	923
0.2-0.3	1602
0.3-0.4	2789
0.4-0.5	1790
0.5-0.6	1016
0.6-0.7	643
0.7-0.8	136
0.8-0.85	8
0.85-0.9	10
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6901	Remote Similarity	NPD3062	Approved
0.6901	Remote Similarity	NPD3059	Approved
0.6901	Remote Similarity	NPD3061	Approved
0.6905	Remote Similarity	NPD3134	Approved
0.6909	Remote Similarity	NPD7090	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID262253 OpenBabel06191716062D 23 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 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 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5351344
ChEMBL	CHEMBL67
ZINC

Physicochemical Properties

Molecular Weight:	316.13
ALogP:	-0.1997
MLogP:	2.89
XLogP:	3.375
# Rotatable Bonds:	11
Polar Surface Area:	57.15
# H-Bond Aceptor:	0
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	23

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