NPASS Natural Product

Natural Product: NPC219900

Natural Product ID:	NPC219900
Common Name:	3-(-2-((1R,4As,5R,8Ar)-5,8A-Dimethyl-2-Methylene-5-(((3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-Yloxy)Methyl)Decahydronaphthalen-1-Yl)Vinyl)Furan-2(5H)-One
IUPAC Name:	4-[2-[(1R,4aS,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:
Molecular Formula:	C26H40O8
Standard InCHIKey:	YGCYRQKJYWQXHG-GQBKZCKISA-N
Standard InCHI:	InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19-,20-,21+,22-,24?,25+,26+/m1/s1
Canonical SMILES:	OC[C@H]1OC(OC[C@]2(C)CCC[C@@]3([C@@H]2CCC(=C)[C@H]3CCC2=CCOC2=O)C)[C@@H]([C@H]([C@@H]1O)O)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	Collection Location	Collection Time	Reference
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota				TM-MC*
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota				TCMID*

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Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000	nM	22264489
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	81.44	%	22264489

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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 NPC219900 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	151
0.1-0.2	727
0.2-0.3	2478
0.3-0.4	4504
0.4-0.5	8848
0.5-0.6	6285
0.6-0.7	4580
0.7-0.8	2859
0.8-0.85	426
0.85-0.9	25
0.9-0.95	4
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC476882
0.819	Intermediate Similarity	NPC476767
0.8198	Intermediate Similarity	NPC470063
0.8198	Intermediate Similarity	NPC194951
0.8198	Intermediate Similarity	NPC174836

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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 NPC219900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1159
0.2-0.3	3306
0.3-0.4	2837
0.4-0.5	1057
0.5-0.6	368
0.6-0.7	222
0.7-0.8	48
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6296	Remote Similarity	NPD7154	Phase 3
0.6299	Remote Similarity	NPD6335	Approved
0.6303	Remote Similarity	NPD5174	Approved
0.6303	Remote Similarity	NPD5175	Approved
0.6325	Remote Similarity	NPD4700	Approved

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Structure

CID219900 OpenBabel06191716012D 34 37 0 0 1 0 0 0 0 0999 V2000 4.9641 0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6097 2.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2788 2.9345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3660 2.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8007 3.5926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2321 2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0575 4.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7788 3.8005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 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 15 2 0 0 0 0 4 10 1 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 27 1 0 0 0 0 14 25 1 0 0 0 0 14 33 1 0 0 0 0 15 17 1 0 0 0 0 16 23 1 0 0 0 0 17 26 1 6 0 0 0 18 13 1 6 0 0 0 18 20 1 0 0 0 0 18 34 1 0 0 0 0 19 25 1 6 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 24 1 0 0 0 0 22 30 1 1 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 24 34 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	45358137
ChEMBL	CHEMBL1951640
ZINC

Physicochemical Properties

Molecular Weight:	480.27
ALogP:	-0.7356
MLogP:	3.44
XLogP:	3.792
# Rotatable Bonds:	13
Polar Surface Area:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	34

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