NPASS Natural Product

Natural Product: NPC170844

Natural Product ID:	NPC170844
Common Name:	Combretastatin
IUPAC Name:	5-[(2R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol
Synonyms:	Combretastatin
Molecular Formula:	C18H22O6
Standard InCHIKey:	LGZKGOGODCLQHG-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C18H22O6/c1-21-15-6-5-11(8-14(15)20)7-13(19)12-9-16(22-2)18(24-4)17(10-12)23-3/h5-6,8-10,13,19-20H,7H2,1-4H3/t13-/m1/s1
Canonical SMILES:	COc1cc(cc(c1OC)OC)[C@@H](Cc1ccc(c(c1)O)OC)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
NPO32832	combretum caffrum	Species	Combretaceae	Eukaryota				PMID[3668557]

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Biological Activity

Activity Type	# Activity
ED50	2
GI50	4
IC50	2
Others	5

Activity Type	# Activity
Cell Line	5
Others	7
Protein Complex	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	10	nM	18197614
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.011	ug/ml	24742384
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.1	ug/ml	17722904
NPT2	Others	Unspecified		Activity	=	34	%	18500841
NPT2	Others	Unspecified		Activity	=	71	%	24742384
NPT2	Others	Unspecified		Activity	=	0	%	24742384
NPT2	Others	Unspecified		Activity	=	51	%	24742384
NPT2	Others	Unspecified		ID50	=	11	nM	25419616
NPT2	Others	Unspecified		GI50	=	20	nM	12444675
NPT2	Others	Unspecified		IC50	=	5000	nM	18625769

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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 NPC170844 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	262
0.1-0.2	1064
0.2-0.3	2492
0.3-0.4	7017
0.4-0.5	6450
0.5-0.6	2484
0.6-0.7	4570
0.7-0.8	4741
0.8-0.85	961
0.85-0.9	492
0.9-0.95	287
0.95-1	69

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Similarity Score	Similarity Level	Natural Product ID
0.9225	High Similarity	NPC263064
0.9231	High Similarity	NPC164787
0.9231	High Similarity	NPC165155
0.9231	High Similarity	NPC34103
0.9231	High Similarity	NPC24490

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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 NPC170844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	851
0.2-0.3	1603
0.3-0.4	2658
0.4-0.5	1850
0.5-0.6	1024
0.6-0.7	697
0.7-0.8	206
0.8-0.85	13
0.85-0.9	2
0.9-0.95	2
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.705	Intermediate Similarity	NPD2232	Approved
0.7055	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD52	Approved
0.7059	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7526	Approved

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Structure

NPC170844 OpenBabel07101718222D 24 25 0 0 1 0 0 0 0 0999 V2000 -6.9282 4.0000 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -4.3301 2.5000 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 -4.3301 1.5000 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 2 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 12 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 12 13 1 0 0 0 0 13 19 1 1 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	9895264
ChEMBL	CHEMBL246600
ZINC

Physicochemical Properties

Molecular Weight:	334.14
ALogP:	-1.1158
MLogP:	2.78
XLogP:	1.707
# Rotatable Bonds:	13
Polar Surface Area:	77.38
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	24

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