NPASS Natural Product

Natural Product: NPC187616

Natural Product ID:	NPC187616
Common Name:	Licarin A
IUPAC Name:	2-methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
Synonyms:	NSC-16743
Molecular Formula:	C20H22O4
Standard InCHIKey:	ITDOFWOJEDZPCF-FNINDUDTSA-N
Standard InCHI:	InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+/t12-,19-/m0/s1
Canonical SMILES:	C/C=C/c1cc2c(c(c1)OC)O[C@@H]([C@H]2C)c1ccc(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	Reference
NPO1146	Cassinia quinquefaria	Species	Asteraceae	Eukaryota		UNPD*
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota		UNPD*
NPO17326	Lyngbya polychroa	Species	Oscillatoriaceae	Bacteria		UNPD*
NPO17370	Seseli bocconi	Species	Apiaceae	Eukaryota		UNPD*
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota		UNPD*
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	Leaves	PMID[19880317]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria		UNPD*
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota		TM-MC*
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial parts	PMID[24387347]
NPO23760	Scytonema hofmannii	Species	Scytonemataceae	Bacteria		UNPD*

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Biological Activity

Activity Type	# Activity
ED50	1
IC50	6
Others	3
Potency	11

Activity Type	# Activity
Cell Line	1
Individual Protein	11
Others	9

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		517.4	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		25929	nM	PubChem BioAssay data set
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency		7943.3	nM	PubChem BioAssay data set
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency		35481.3	nM	PubChem BioAssay data set
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency		39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	9730	nM	19880317
NPT2	Others	Unspecified		Ratio IC50	=	35.5		19880317
NPT2	Others	Unspecified		IC50	>	999000	nM	19880317
NPT2	Others	Unspecified		IC50	=	489000	nM	19880317
NPT2	Others	Unspecified		IC50	=	112000	nM	19880317

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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 NPC187616 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	266
0.1-0.2	1062
0.2-0.3	2311
0.3-0.4	5812
0.4-0.5	7514
0.5-0.6	2280
0.6-0.7	5312
0.7-0.8	4893
0.8-0.85	787
0.85-0.9	495
0.9-0.95	135
0.95-1	22

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Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC324492
0.8929	High Similarity	NPC317053
0.8931	High Similarity	NPC72529
0.8931	High Similarity	NPC474178
0.8931	High Similarity	NPC252307

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 NPC187616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	843
0.2-0.3	1475
0.3-0.4	2597
0.4-0.5	1917
0.5-0.6	1040
0.6-0.7	748
0.7-0.8	268
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7163	Intermediate Similarity	NPD2233	Approved
0.7163	Intermediate Similarity	NPD1840	Phase 2
0.7163	Intermediate Similarity	NPD2232	Approved
0.717	Intermediate Similarity	NPD8455	Phase 2
0.7171	Intermediate Similarity	NPD3892	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID187616 OpenBabel06191715572D 24 26 0 0 1 0 0 0 0 0999 V2000 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 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 5 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 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 2 1 1 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 15 20 2 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 14 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281836
ChEMBL	CHEMBL463526
ZINC

Physicochemical Properties

Molecular Weight:	326.15
ALogP:	0.2723
MLogP:	3.22
XLogP:	4.363
# Rotatable Bonds:	9
Polar Surface Area:	47.92
# H-Bond Aceptor:	0
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	24

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