NPASS Natural Product

Natural Product: NPC165133

Natural Product ID:	NPC165133
Common Name:	Dihydroguaiaretic Acid
IUPAC Name:	4-[4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
Synonyms:
Molecular Formula:	C20H26O4
Standard InCHIKey:	ADFOLUXMYYCTRR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3
Canonical SMILES:	COc1cc(ccc1O)CC(C(Cc1ccc(c(c1)OC)O)C)C
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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota				TM-MC*

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Biological Activity

Activity Type	# Activity
EC50	1
GI50	60
IC50	1
LD50	1
Others	1

Activity Type	# Activity
Cell Line	60
Individual Protein	2
Organism	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50		14962.36	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		9289.66	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		9397.23	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		22542.39	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		20941.12	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		9682.78	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		20044.72	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		21037.78	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	210	nM	24831826
NPT306	Cell Line	PC-3	Homo sapiens	GI50		10814.34	nM	PubChem BioAssay data set

Showing 1 to 10 of 64 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 NPC165133 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	218
0.1-0.2	1107
0.2-0.3	2249
0.3-0.4	7878
0.4-0.5	5674
0.5-0.6	2900
0.6-0.7	6420
0.7-0.8	3335
0.8-0.85	622
0.85-0.9	342
0.9-0.95	127
0.95-1	17

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Similarity Score	Similarity Level	Natural Product ID
0.8862	High Similarity	NPC118787
0.8862	High Similarity	NPC163332
0.8871	High Similarity	NPC304622
0.8871	High Similarity	NPC170844
0.8871	High Similarity	NPC476968

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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 NPC165133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	931
0.2-0.3	1219
0.3-0.4	2562
0.4-0.5	2077
0.5-0.6	1084
0.6-0.7	795
0.7-0.8	235
0.8-0.85	15
0.85-0.9	4
0.9-0.95	4
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7105	Intermediate Similarity	NPD4965	Approved
0.7105	Intermediate Similarity	NPD4966	Approved
0.7105	Intermediate Similarity	NPD4967	Phase 2
0.712	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1535	Discovery

Showing 1 to 5 of 200 entries

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Structure

CID165133 OpenBabel06191715532D 24 25 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 -5.1962 -3.0000 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 -6.0622 -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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 3 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 -0.8660 -1.5000 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 -0.8660 0.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -5.1962 0.0000 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	161924
ChEMBL	CHEMBL1976696
ZINC

Physicochemical Properties

Molecular Weight:	330.18
ALogP:	-0.115
MLogP:	3.22
XLogP:	5.238
# Rotatable Bonds:	13
Polar Surface Area:	58.92
# H-Bond Aceptor:	0
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	24

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