NPASS Natural Product

Natural Product: NPC116178

Natural Product ID:	NPC116178
Common Name:	Gravacridondiolmonomethyl Ether
IUPAC Name:	5-hydroxy-2-(2-hydroxy-1-methoxypropan-2-yl)-11-methyl-1,2-dihydrofuro[2,3-c]acridin-6-one
Synonyms:	Gravacridondiolmonomethyl Ether
Molecular Formula:	C20H21NO5
Standard InCHIKey:	YYTVGIBSAJVHGD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H21NO5/c1-20(24,10-25-3)16-8-12-15(26-16)9-14(22)17-18(12)21(2)13-7-5-4-6-11(13)19(17)23/h4-7,9,16,22,24H,8,10H2,1-3H3
Canonical SMILES:	COCC(C1Oc2c(C1)c1c(c(c2)O)c(=O)c2c(n1C)cccc2)(O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	PMID[19191562]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	TCM_Taiwan*
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	HerDing*
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	TCMID*

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Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3000	nM	19191562
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	3000	nM	19191562
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3000	nM	19191562

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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 NPC116178 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	276
0.1-0.2	1272
0.2-0.3	3772
0.3-0.4	8263
0.4-0.5	3571
0.5-0.6	7165
0.6-0.7	5866
0.7-0.8	664
0.8-0.85	15
0.85-0.9	17
0.9-0.95	4
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.7234	Intermediate Similarity	NPC177354
0.7234	Intermediate Similarity	NPC107572
0.7234	Intermediate Similarity	NPC161506
0.7234	Intermediate Similarity	NPC37496
0.7234	Intermediate Similarity	NPC125855

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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 NPC116178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	688
0.2-0.3	876
0.3-0.4	1687
0.4-0.5	2547
0.5-0.6	2266
0.6-0.7	825
0.7-0.8	54
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6682	Remote Similarity	NPD2907	Approved
0.6682	Remote Similarity	NPD4605	Approved
0.6682	Remote Similarity	NPD2491	Approved
0.6682	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3533	Approved

Showing 1 to 5 of 200 entries

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Structure

CID116178 OpenBabel06191715472D 26 29 0 0 1 0 0 0 0 0999 V2000 -4.3005 2.4487 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 -2.9345 4.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 1.7321 -2.0000 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 -1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 2.8147 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 0.8660 -0.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 3 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 -0.8660 -0.5000 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 -3.4345 1.9487 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -4.3005 1.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 3.6808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5317837
ChEMBL	CHEMBL560820
ZINC

Physicochemical Properties

Molecular Weight:	355.14
ALogP:	-1.0966
MLogP:	3
XLogP:	1.779
# Rotatable Bonds:	8
Polar Surface Area:	79.23
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	26

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