NPASS Natural Product

Natural Product: NPC176814

Natural Product ID:	NPC176814
Common Name:	Arctigenin
IUPAC Name:	(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Synonyms:	(-)-Arctigenin; Arctigenin
Molecular Formula:	C21H24O6
Standard InCHIKey:	NQWVSMVXKMHKTF-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
Canonical SMILES:	COc1cc(ccc1OC)C[C@H]1COC(=O)[C@@H]1Cc1ccc(c(c1)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	Reference
NPO10398	Myrica gale	Species	Myricaceae	Eukaryota			UNPD*
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota			TM-MC*
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota			TCM_Taiwan*
NPO10799	Espeletia moritziana	Species	Asteraceae	Eukaryota			UNPD*
NPO11869	Vernonia leopoldi	Species	Asteraceae	Eukaryota			UNPD*
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota			TM-MC*
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	Stem barks	Kunming, Yunnan Province, China	PMID[18986199]
NPO12713	Brachylaena ramiflora	Species	Asteraceae	Eukaryota			UNPD*
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota			TCM_Taiwan*
NPO13045	Kielmeyera albopunctata	Species	Calophyllaceae	Eukaryota			UNPD*

Showing 1 to 10 of 58 entries

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Biological Activity

Activity Type	# Activity
AC50	4
EC50	1
IC50	6
MIC	2
Others	13
Potency	11

Activity Type	# Activity
Cell Line	8
Individual Protein	14
Organism	4
Others	11

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	15848.93	nM	PubChem BioAssay data set
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	Activity	=	60	%	9834179
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	10	nM	18077363
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	260000	nM	18986199
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	Inhibition	<	5	%	8568830
NPT171	Cell Line	MRC5	Homo sapiens	CC50	=	76000	nM	17239594
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	IC50	=	2100	nM	17239594
NPT2	Others	Unspecified		Ratio CC50/IC50	=	36		17239594
NPT2	Others	Unspecified		MIC	=	69000	nM	9834179

Showing 1 to 10 of 34 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 NPC176814 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	186
0.1-0.2	857
0.2-0.3	1784
0.3-0.4	4211
0.4-0.5	8652
0.5-0.6	2926
0.6-0.7	6051
0.7-0.8	5451
0.8-0.85	543
0.85-0.9	192
0.9-0.95	27
0.95-1	9

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Similarity Score	Similarity Level	Natural Product ID
0.8542	High Similarity	NPC236166
0.855	High Similarity	NPC242372
0.855	High Similarity	NPC257976
0.855	High Similarity	NPC4181
0.855	High Similarity	NPC164778

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 NPC176814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	756
0.2-0.3	1281
0.3-0.4	2196
0.4-0.5	2289
0.5-0.6	1336
0.6-0.7	842
0.7-0.8	242
0.8-0.85	17
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7114	Intermediate Similarity	NPD5688	Approved
0.7114	Intermediate Similarity	NPD5689	Approved
0.7119	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2313	Discontinued
0.7123	Intermediate Similarity	NPD3145	Approved

Showing 1 to 5 of 200 entries

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Structure

CID176814 OpenBabel06191715552D 27 29 0 0 1 0 0 0 0 0999 V2000 4.0428 -5.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3975 -5.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 -2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 -3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7248 -2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 -2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0981 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8838 -4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9328 -3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0917 -5.1727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1896 -4.5546 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 27 1 0 0 0 0 15 8 1 6 0 0 0 15 16 1 0 0 0 0 16 9 1 1 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	64981
ChEMBL	CHEMBL435734
ZINC

Physicochemical Properties

Molecular Weight:	372.16
ALogP:	-0.5036
MLogP:	3.11
XLogP:	2.934
# Rotatable Bonds:	11
Polar Surface Area:	74.22
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	27

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