NPASS Natural Product

Natural Product: NPC170779

Natural Product ID:	NPC170779
Common Name:	(-)-Licarin B
IUPAC Name:	5-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]-1,3-benzodioxole
Synonyms:
Molecular Formula:	C20H20O4
Standard InCHIKey:	DMMQXURQRMNSBM-NSWCWGQASA-N
Standard InCHI:	InChI=1S/C20H20O4/c1-4-5-13-8-15-12(2)19(24-20(15)18(9-13)21-3)14-6-7-16-17(10-14)23-11-22-16/h4-10,12,19H,11H2,1-3H3/b5-4+/t12-,19-/m0/s1
Canonical SMILES:	C/C=C/c1cc2c(c(c1)OC)O[C@@H]([C@H]2C)c1ccc2c(c1)OCO2
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
NPO1382	Hyptis tomentosa	Species	Lamiaceae	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]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	Leaves	PMID[19880317]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota		UNPD*
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	Leaves	PMID[19880317]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota		UNPD*

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Biological Activity

Activity Type	# Activity
IC50	7
Others	4

Activity Type	# Activity
Individual Protein	2
Others	9

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	14300	nM	19880317
NPT2	Others	Unspecified		Ratio IC50	=	426		19880317
NPT2	Others	Unspecified		IC50	=	488000	nM	19880317
NPT2	Others	Unspecified		IC50	=	290000	nM	19880317
NPT2	Others	Unspecified		IC50	=	54600	nM	19880317
NPT2	Others	Unspecified		IC50	=	50600	nM	24387347
NPT2	Others	Unspecified		Inhibition	=	86.7	%	24387347
NPT2	Others	Unspecified		Inhibition	=	42.5	%	24387347
NPT2	Others	Unspecified		Inhibition	=	5.3	%	24387347
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	366000	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 NPC170779 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	342
0.1-0.2	1159
0.2-0.3	2470
0.3-0.4	6786
0.4-0.5	6623
0.5-0.6	2895
0.6-0.7	6997
0.7-0.8	2880
0.8-0.85	513
0.85-0.9	175
0.9-0.95	43
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.8529	High Similarity	NPC207400
0.8531	High Similarity	NPC226540
0.854	High Similarity	NPC185680
0.854	High Similarity	NPC145722
0.854	High Similarity	NPC256776

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 NPC170779 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	903
0.2-0.3	1470
0.3-0.4	2763
0.4-0.5	1872
0.5-0.6	1022
0.6-0.7	656
0.7-0.8	155
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6867	Remote Similarity	NPD7229	Phase 3
0.6867	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7446	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID170779 OpenBabel06191715542D 24 27 0 0 1 0 0 0 0 0999 V2000 4.4152 3.3090 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 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 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 1.6750 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 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 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6705 -0.3934 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 -0.0570 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 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 0.6011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -0.8002 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 4 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 11 23 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 22 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 21 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	10860310
ChEMBL	CHEMBL578403
ZINC

Physicochemical Properties

Molecular Weight:	324.14
ALogP:	0.4817
MLogP:	3.22
XLogP:	4.809
# Rotatable Bonds:	6
Polar Surface Area:	36.92
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	24

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