NPASS Natural Product

Natural Product: NPC198160

Natural Product ID:	NPC198160
Common Name:	Rutacridone
IUPAC Name:	(2R)-5-hydroxy-11-methyl-2-prop-1-en-2-yl-1,2-dihydrofuro[2,3-c]acridin-6-one
Synonyms:	Rutacridone
Molecular Formula:	C19H17NO3
Standard InCHIKey:	FHAGACMCMQYSNX-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C19H17NO3/c1-10(2)15-8-12-16(23-15)9-14(21)17-18(12)20(3)13-7-5-4-6-11(13)19(17)22/h4-7,9,15,21H,1,8H2,2-3H3/t15-/m1/s1
Canonical SMILES:	CC(=C)[C@@H]1Oc2c(C1)c1c(c(c2)O)c(=O)c2c(n1C)cccc2
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	PMID[19191562]
NPO22971	Ophiopogon planiscapus	Species	Asparagaceae	Eukaryota	TCMID*
NPO26550	Ruscus aculeatus	Species	Asparagaceae	Eukaryota	TCMID*
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	TCMID*
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 NPC198160 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	1267
0.2-0.3	4017
0.3-0.4	8386
0.4-0.5	3230
0.5-0.6	7633
0.6-0.7	5504
0.7-0.8	539
0.8-0.85	20
0.85-0.9	14
0.9-0.95	6
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.7219	Intermediate Similarity	NPC195621
0.7219	Intermediate Similarity	NPC470132
0.7219	Intermediate Similarity	NPC111786
0.7219	Intermediate Similarity	NPC312973
0.7222	Intermediate Similarity	NPC67401

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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 NPC198160 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	701
0.2-0.3	875
0.3-0.4	1565
0.4-0.5	2512
0.5-0.6	2401
0.6-0.7	826
0.7-0.8	62
0.8-0.85	1
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
0.665	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3802	Phase 3
0.6652	Remote Similarity	NPD3437	Discontinued
0.6652	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7223	Discontinued

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Structure

CID198160 OpenBabel06191715582D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.9345 2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4345 1.9487 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 2.5981 -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 -3.4345 1.9487 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 -2.9345 1.0827 0.0000 C 0 0 2 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 -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 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 -3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 20 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 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 10 1 1 0 0 0 15 23 1 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11623705
ChEMBL	CHEMBL563582
ZINC

Physicochemical Properties

Molecular Weight:	307.12
ALogP:	0.4032
MLogP:	3.11
XLogP:	2.756
# Rotatable Bonds:	4
Polar Surface Area:	49.77
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	23

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