NPASS Natural Product

Natural Product: NPC40432

Natural Product ID:	NPC40432
Common Name:	(+)-Pinoresinol
IUPAC Name:	4-[(3R,3aS,6R,6aS)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Synonyms:	(+)-Pinoresinol
Molecular Formula:	C20H22O6
Standard InCHIKey:	HGXBRUKMWQGOIE-NSMLZSOPSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m1/s1
Canonical SMILES:	COc1cc(ccc1O)[C@@H]1OC[C@@H]2[C@H]1CO[C@H]2c1ccc(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
NPO10211	Pajanelia multijuga	NA	NA	NA		UNPD*
NPO11162	Aplidium glabrum	Species	Polyclinidae	Eukaryota		UNPD*
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota		UNPD*
NPO12128	Ipomoea purpurea	Species	Convolvulaceae	Eukaryota		TM-MC*
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota		UNPD*
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	PMID[10514313]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota		TM-MC*
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota		TM-MC*
NPO17039	Ipomoea nil	Species	Convolvulaceae	Eukaryota		TM-MC*
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota		TM-MC*

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Biological Activity

Activity Type	# Activity
IC50	29
Ki	2
Others	7

Activity Type	# Activity
Cell Line	15
Individual Protein	4
Organism	1
Others	18

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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	=	8.66	ug/ml	10.1007/s00044-009-9217-5
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	33500	nM	22079762
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	45100	nM	25592708
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10	ug/ml	10514313
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	40	ug/ml	18603435
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000	nM	26988298
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	92500	nM	18440233
NPT2	Others	Unspecified		IC50	=	49	ug/ml	18068371
NPT2	Others	Unspecified		IC50	>	100000	nM	18440233
NPT2	Others	Unspecified		IC50	>	40	ug/ml	18603435

Showing 1 to 10 of 35 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 NPC40432 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	249
0.1-0.2	986
0.2-0.3	2187
0.3-0.4	5625
0.4-0.5	7853
0.5-0.6	2514
0.6-0.7	6338
0.7-0.8	3731
0.8-0.85	734
0.85-0.9	494
0.9-0.95	137
0.95-1	41

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Similarity Score	Similarity Level	Natural Product ID
0.8976	High Similarity	NPC293701
0.8976	High Similarity	NPC94276
0.8976	High Similarity	NPC48990
0.8984	High Similarity	NPC50683
0.8984	High Similarity	NPC112571

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 NPC40432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	805
0.2-0.3	1429
0.3-0.4	2599
0.4-0.5	2057
0.5-0.6	1072
0.6-0.7	746
0.7-0.8	200
0.8-0.85	14
0.85-0.9	0
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7045	Intermediate Similarity	NPD5451	Approved
0.7047	Intermediate Similarity	NPD3539	Phase 1
0.7047	Intermediate Similarity	NPD2438	Suspended
0.7048	Intermediate Similarity	NPD7472	Approved
0.7055	Intermediate Similarity	NPD3062	Approved

Showing 1 to 5 of 200 entries

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Structure

CID40432 OpenBabel06191715372D 26 29 0 0 1 0 0 0 0 0999 V2000 -1.9323 -4.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4277 -0.8494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3413 -1.2561 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 -1.7232 -2.4317 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 -0.9040 0.8613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9040 -0.8613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6187 -1.4371 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 -0.4973 -0.0523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4973 0.0523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4458 -2.2506 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 -2.6368 -2.8384 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 -0.7052 -1.0304 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7052 1.0304 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3594 -2.6574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7413 -3.8329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1609 -1.5304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1609 1.5304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 26 1 0 0 0 0 10 25 1 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 10 1 6 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 11 1 1 0 0 0 19 25 1 0 0 0 0 20 12 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	12309636
ChEMBL	CHEMBL267963
ZINC

Physicochemical Properties

Molecular Weight:	358.14
ALogP:	-2.0222
MLogP:	3
XLogP:	1.684
# Rotatable Bonds:	8
Polar Surface Area:	77.38
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	26

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