NPASS Natural Product

Natural Product: NPC76213

Natural Product ID:	NPC76213
Common Name:	(R)-(+)-Coclaurine
IUPAC Name:	(1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Synonyms:	(+)-1R-Cocluaurine; (R)-(+)-Coclaurine
Molecular Formula:	C17H19NO3
Standard InCHIKey:	LVVKXRQZSRUVPY-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m1/s1
Canonical SMILES:	COc1cc2CCN[C@@H](c2cc1O)Cc1ccc(cc1)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO12170	Solanum lasiocarpum	Species	Solanaceae	Eukaryota	UNPD*
NPO18354	Meiothermus ruber	Species	Thermaceae	Bacteria	UNPD*
NPO25388	Siliquariaspongia japonica	NA	NA	NA	UNPD*
NPO26332	Ramalina tumidula	Species	Ramalinaceae	Eukaryota	UNPD*
NPO27216	Oreodaphne porosa	NA	NA	NA	UNPD*
NPO27468	Rhizopogon roseolus	Species	Rhizopogonaceae	Eukaryota	UNPD*
NPO27522	Gongronella urceolifera	Species	Cunninghamellaceae	Eukaryota	UNPD*
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	UNPD*
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	UNPD*
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
EC50	2
IC50	2

Activity Type	# Activity
Individual Protein	2
Organism	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	EC50	=	0.8	ug/ml	18316190
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	IC50	=	240	nM	9644051
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	IC50	=	130	nM	9644051
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2800	nM	20187635

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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 NPC76213 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	173
0.1-0.2	1100
0.2-0.3	4426
0.3-0.4	8373
0.4-0.5	3536
0.5-0.6	8616
0.6-0.7	3687
0.7-0.8	683
0.8-0.85	150
0.85-0.9	86
0.9-0.95	44
0.95-1	15

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Similarity Score	Similarity Level	Natural Product ID
0.8239	Intermediate Similarity	NPC59028
0.8242	Intermediate Similarity	NPC199465
0.8242	Intermediate Similarity	NPC128560
0.8242	Intermediate Similarity	NPC229166
0.8253	Intermediate Similarity	NPC114364

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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 NPC76213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	631
0.2-0.3	936
0.3-0.4	1496
0.4-0.5	2663
0.5-0.6	2086
0.6-0.7	876
0.7-0.8	283
0.8-0.85	34
0.85-0.9	8
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7256	Intermediate Similarity	NPD1969	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1973	Approved
0.7256	Intermediate Similarity	NPD1972	Approved
0.7267	Intermediate Similarity	NPD7124	Phase 2
0.7267	Intermediate Similarity	NPD4481	Phase 3

Showing 1 to 5 of 200 entries

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Structure

CID76213 OpenBabel06191715412D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.7321 0.0000 0.0000 C 0 0 0 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 5.1962 1.0000 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 6.0622 1.5000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 1.7321 -0.0000 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 0.8660 1.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 11 2 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	440989
ChEMBL	CHEMBL256448
ZINC

Physicochemical Properties

Molecular Weight:	285.14
ALogP:	-1.1136
MLogP:	2.89
XLogP:	2.236
# Rotatable Bonds:	6
Polar Surface Area:	61.72
# H-Bond Aceptor:	1
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	21

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