NPASS Natural Product

Natural Product: NPC232316

Natural Product ID:	NPC232316
Common Name:	Mesodihydroguaiaretic Acid
IUPAC Name:	4-[(2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
Synonyms:	Meso-Dihydroguaiaretic Acid; Meso-Dihyroguaiareticacid; Mesodihydroguaiaretic Acid
Molecular Formula:	C20H26O4
Standard InCHIKey:	ADFOLUXMYYCTRR-OKILXGFUSA-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/t13-,14+
Canonical SMILES:	COc1cc(ccc1O)C[C@H]([C@H](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
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota				UNPD*
NPO11693	Spatangus purpureus	Species	Spatangidae	Eukaryota				UNPD*
NPO12432	Chaenorhinum origanifolium	Species	Plantaginaceae	Eukaryota				UNPD*
NPO12884	Piper murrayanum	Species	Piperaceae	Eukaryota				UNPD*
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota				UNPD*
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota				UNPD*
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	Stems	Honghe Prefecture of Yunnan Province, China	2005-OCT	PMID[18278869]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria				UNPD*
NPO19979	Schisandra glaucescens	Species	Schisandraceae	Eukaryota	fruit			PMID[24927000]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota				TM-MC*

Showing 1 to 10 of 38 entries

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Biological Activity

Activity Type	# Activity
EC50	2
IC50	7
LD50	1
MIC	4
Others	32
Potency	20

Activity Type	# Activity
Cell Line	13
Individual Protein	19
Organism	11
Others	23

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	15700	nM	24927000
NPT1	Others	Radical scavenging activity		IC50	=	34640	nM	24927000
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		20596.2	nM	PubChem BioAssay data set
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency		28183.8	nM	PubChem BioAssay data set
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency		1122	nM	PubChem BioAssay data set
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	50000000	nM	27210431
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	49150	nM	18278869
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	24900	nM	19413342
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		10322.5	nM	PubChem BioAssay data set
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency		35481.3	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 NPC232316 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

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 NPC232316 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

CID232316 OpenBabel06191716032D 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 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 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 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 1 1 6 0 0 0 13 14 1 0 0 0 0 14 2 1 1 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	476856
ChEMBL	CHEMBL430464
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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