NPASS Natural Product

Natural Product: NPC81515

Natural Product ID:	NPC81515
Common Name:	Forsythiaside
IUPAC Name:	[(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Forsythiaside
Molecular Formula:	C29H36O15
Standard InCHIKey:	DTOUWTJYUCZJQD-UJERWXFOSA-N
Standard InCHI:	InChI=1S/C29H36O15/c1-13-22(35)23(36)25(38)29(42-13)41-12-20-27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)24(37)26(39)28(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29+/m0/s1
Canonical SMILES:	O=C(O[C@@H]1[C@@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O[C@H]([C@@H]([C@H]1O)O)OCCc1ccc(c(c1)O)O)/C=C/c1ccc(c(c1)O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Show entries

Search:

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Reference
NPO10000	Rehmanniae radix praeparata	NA	NA	NA			TCMSP*
NPO16764	Penstemon linarioides	Species	Plantaginaceae	Eukaryota			PMID[9834166]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota			TM-MC*
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota			TM-MC*
NPO29584	Forsythiae fructus	NA	NA	NA			TCMSP*
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota			TM-MC*
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota			PMID[9834166]
NPO5912	Globularia alypum	Species	Plantaginaceae	Eukaryota	Aerial parts	Morocco	PMID[16124783]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota			TM-MC*
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota			TM-MC*

Showing 1 to 10 of 10 entries

Previous1Next

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Individual Protein	1
Others	2

Show entries

Search:

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	21000	nM	16124783
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	IC50	=	1900	nM	9834166
NPT2	Others	Unspecified		Activity	=	60.4	%	26422318

Showing 1 to 3 of 3 entries

Previous1Next

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 NPC81515 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	203
0.1-0.2	962
0.2-0.3	2060
0.3-0.4	4653
0.4-0.5	6962
0.5-0.6	5062
0.6-0.7	6344
0.7-0.8	3830
0.8-0.85	574
0.85-0.9	124
0.9-0.95	62
0.95-1	53

Show entries

Search:

Similarity Score	Similarity Level	Natural Product ID
0.8649	High Similarity	NPC150442
0.8657	High Similarity	NPC252114
0.8657	High Similarity	NPC61181
0.8658	High Similarity	NPC131532
0.8662	High Similarity	NPC473873

Showing 1 to 5 of 200 entries

Previous1 2 3 4 5…40Next

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC81515 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	758
0.2-0.3	1442
0.3-0.4	2727
0.4-0.5	2148
0.5-0.6	1268
0.6-0.7	527
0.7-0.8	70
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Show entries

Search:

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6619	Remote Similarity	NPD2684	Approved
0.6621	Remote Similarity	NPD1548	Phase 1
0.6623	Remote Similarity	NPD4140	Approved
0.6642	Remote Similarity	NPD3020	Approved
0.6644	Remote Similarity	NPD4626	Approved

Showing 1 to 5 of 200 entries

Previous1 2 3 4 5…40Next

Structure

CID81515 OpenBabel06191715422D 44 47 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 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 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 6.0622 2.5000 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 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 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 2 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 5 2 0 0 0 0 2 14 1 0 0 0 0 3 6 2 0 0 0 0 3 15 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 40 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 41 1 0 0 0 0 13 1 1 6 0 0 0 13 22 1 0 0 0 0 13 42 1 0 0 0 0 16 18 2 0 0 0 0 16 30 1 0 0 0 0 17 19 2 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 12 1 1 0 0 0 20 27 1 0 0 0 0 20 43 1 0 0 0 0 21 34 2 0 0 0 0 21 44 1 0 0 0 0 22 23 1 0 0 0 0 22 35 1 1 0 0 0 23 25 1 0 0 0 0 23 36 1 6 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 24 37 1 1 0 0 0 25 29 1 0 0 0 0 25 38 1 6 0 0 0 26 28 1 0 0 0 0 26 39 1 6 0 0 0 27 44 1 6 0 0 0 28 40 1 1 0 0 0 28 43 1 0 0 0 0 29 41 1 1 0 0 0 29 42 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281773
ChEMBL	CHEMBL504363
ZINC

Physicochemical Properties

Molecular Weight:	624.21
ALogP:	-4.2978
MLogP:	3
XLogP:	0.227
# Rotatable Bonds:	21
Polar Surface Area:	245.29
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	44

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs