NPASS Natural Product

Natural Product: NPC321166

Natural Product ID:	NPC321166
Common Name:	5-Hydroxy-11-Methyl-2-(2-Methyloxiran-2-Yl)-1,2-Dihydrofuro[2,3-C]Acridin-6-One
IUPAC Name:	5-hydroxy-11-methyl-2-(2-methyloxiran-2-yl)-1,2-dihydrofuro[2,3-c]acridin-6-one
Synonyms:
Molecular Formula:	C19H17NO4
Standard InCHIKey:	YXQGLAPCZDYVLL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO4/c1-19(9-23-19)15-7-11-14(24-15)8-13(21)16-17(11)20(2)12-6-4-3-5-10(12)18(16)22/h3-6,8,15,21H,7,9H2,1-2H3
Canonical SMILES:	Oc1cc2OC(Cc2c2c1c(=O)c1c(n2C)cccc1)C1(C)CO1
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
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota				TCM_Taiwan*

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Biological Activity

Activity Type	# Activity
GI50	69

Activity Type	# Activity
Cell Line	69

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	260.02	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	66.53	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50	49.55	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50	4405.55	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	5533.5	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	887.16	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	4688.13	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	2786.12	nM	PubChem BioAssay data set
NPT306	Cell Line	PC-3	Homo sapiens	GI50	3372.87	nM	PubChem BioAssay data set
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	2992.26	nM	PubChem BioAssay data set

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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 NPC321166 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	278
0.1-0.2	1295
0.2-0.3	3921
0.3-0.4	8283
0.4-0.5	3523
0.5-0.6	7411
0.6-0.7	5663
0.7-0.8	476
0.8-0.85	18
0.85-0.9	15
0.9-0.95	3
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.7173	Intermediate Similarity	NPC83357
0.7173	Intermediate Similarity	NPC285630
0.7173	Intermediate Similarity	NPC312973
0.7173	Intermediate Similarity	NPC142405
0.7173	Intermediate Similarity	NPC301276

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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 NPC321166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	714
0.2-0.3	885
0.3-0.4	1700
0.4-0.5	2570
0.5-0.6	2262
0.6-0.7	767
0.7-0.8	47
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
0.6621	Remote Similarity	NPD5197	Approved
0.6621	Remote Similarity	NPD5194	Approved
0.6621	Remote Similarity	NPD5196	Approved
0.6622	Remote Similarity	NPD7497	Discontinued
0.6624	Remote Similarity	NPD7031	Phase 1

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Structure

CID321166 OpenBabel06191716152D 24 28 0 0 1 0 0 0 0 0999 V2000 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5388 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0029 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2709 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.4049 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0029 0.5000 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 2.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 12 2 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281850
ChEMBL	CHEMBL1968498
ZINC

Physicochemical Properties

Molecular Weight:	323.12
ALogP:	-0.7386
MLogP:	3
XLogP:	2.278
# Rotatable Bonds:	4
Polar Surface Area:	62.3
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	24

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