NPASS Natural Product

Natural Product: NPC141765

Natural Product ID:	NPC141765
Common Name:	Syringaresinol
IUPAC Name:	4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
Synonyms:	(+)-Syringaresinol; (+/-)-Syringaresinol
Molecular Formula:	C22H26O8
Standard InCHIKey:	KOWMJRJXZMEZLD-HCIHMXRSSA-N
Standard InCHI:	InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,21+,22+/m0/s1
Canonical SMILES:	COc1cc(cc(c1O)OC)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1cc(OC)c(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	Reference
NPO1033	Plectranthus nummularius	Species	Lamiaceae	Eukaryota	UNPD*
NPO10659	Helminthosporium victoriae	Species	Massarinaceae	Eukaryota	UNPD*
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	TM-MC*
NPO10960	Machilus odoratissima	Species	Lauraceae	Eukaryota	UNPD*
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	TM-MC*
NPO10999	Corynebacterium matruchotii	Species	Corynebacteriaceae	Bacteria	UNPD*
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	UNPD*
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	TM-MC*
NPO11135	Sideritis perfoliata	Species	Lamiaceae	Eukaryota	UNPD*
NPO11153	Entada polystachya	Species	Fabaceae	Eukaryota	UNPD*

Showing 1 to 10 of 234 entries

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Biological Activity

Activity Type	# Activity
EC50	1
ED50	7
IC50	18
Kd	2
MIC	1
Others	19

Activity Type	# Activity
Cell Line	28
Individual Protein	12
Organism	3
Others	5

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	EC50	=	18110	nM	27450788
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Kd	=	27620	nM	27450788
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	47000	nM	18986199
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14800	nM	21435874
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000	nM	25592708
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	21600	nM	25666824
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	15.5	ug/ml	1593281
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.27	ug/ml	1453182
NPT140	Organism	Artemia	Artemia	LC50	=	13.6	ug/ml	1593281
NPT140	Organism	Artemia	Artemia	LC50	=	0.65	ug/ml	1453182

Showing 1 to 10 of 44 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 NPC141765 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	270
0.1-0.2	1034
0.2-0.3	2430
0.3-0.4	6275
0.4-0.5	7262
0.5-0.6	2579
0.6-0.7	5421
0.7-0.8	4164
0.8-0.85	724
0.85-0.9	558
0.9-0.95	153
0.95-1	19

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Similarity Score	Similarity Level	Natural Product ID
0.8963	High Similarity	NPC256262
0.8963	High Similarity	NPC112246
0.8971	High Similarity	NPC3072
0.8971	High Similarity	NPC46277
0.8971	High Similarity	NPC477938

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 NPC141765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	833
0.2-0.3	1618
0.3-0.4	2734
0.4-0.5	1866
0.5-0.6	1080
0.6-0.7	636
0.7-0.8	128
0.8-0.85	11
0.85-0.9	4
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6899	Remote Similarity	NPD52	Approved
0.6901	Remote Similarity	NPD5126	Approved
0.6901	Remote Similarity	NPD6516	Phase 2
0.6901	Remote Similarity	NPD5846	Approved
0.6901	Remote Similarity	NPD5125	Phase 3

Showing 1 to 5 of 200 entries

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Structure

CID141765 OpenBabel06191715502D 30 33 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 -5.0638 -1.0751 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 -1.7321 2.0000 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 -2.4277 -0.8494 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 -1.7321 -0.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4973 -0.0523 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4973 0.0523 0.0000 C 0 0 1 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 -3.3413 -1.2561 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 -0.8660 0.5000 0.0000 C 0 0 0 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 0.0000 -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 2 0 0 0 0 0 0 0 0 0 0.7052 1.0304 0.0000 C 0 0 2 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 0.8660 0.5000 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 -4.1503 -0.6683 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 1.5000 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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 11 1 0 0 0 0 6 16 2 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 18 2 0 0 0 0 9 30 1 0 0 0 0 10 29 1 0 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 10 1 1 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 20 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 11 1 6 0 0 0 21 29 1 0 0 0 0 22 12 1 6 0 0 0 22 30 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	443023
ChEMBL	CHEMBL361362
ZINC

Physicochemical Properties

Molecular Weight:	418.16
ALogP:	-2.1258
MLogP:	3
XLogP:	0.796
# Rotatable Bonds:	12
Polar Surface Area:	95.84
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	30

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