NPASS Natural Product

Natural Product: NPC133156

Natural Product ID:	NPC133156
Common Name:	1,3,5-Trihydroxy-2,8-Bis(3-Methylbut-2-Enyl)-10-Methyl-9-Acridone
IUPAC Name:	1,3,5-trihydroxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9-one
Synonyms:
Molecular Formula:	C24H27NO4
Standard InCHIKey:	DYCRIHPNHAPQTH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H27NO4/c1-13(2)6-8-15-9-11-18(26)22-20(15)24(29)21-17(25(22)5)12-19(27)16(23(21)28)10-7-14(3)4/h6-7,9,11-12,26-28H,8,10H2,1-5H3
Canonical SMILES:	CC(=CCc1c(O)cc2c(c1O)c(=O)c1c(n2C)c(O)ccc1CC=C(C)C)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
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	UNPD*
NPO2786	Clematis flammula	Species	Ranunculaceae	Eukaryota	UNPD*
NPO5476	Hortia arborea	Species	Rutaceae	Eukaryota	UNPD*
NPO7221	Korolkowia sewerzowi	NA	NA	NA	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	2
IC50	5
Ki	1
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Organism	4
Others	2

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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	ED50	=	47.2	nM	11575960
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	52.2	nM	11575960
NPT2	Others	Unspecified		Ratio	=	9		11575960
NPT2	Others	Unspecified		Ratio	=	9.4		11575960
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5300	nM	11575960
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5600	nM	11575960
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7900	nM	11575960
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7100	nM	11575960
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	3900	nM	21277783
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	Ki	=	1200	nM	21277783

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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 NPC133156 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	325
0.1-0.2	1463
0.2-0.3	5512
0.3-0.4	7184
0.4-0.5	6085
0.5-0.6	8273
0.6-0.7	1984
0.7-0.8	32
0.8-0.85	22
0.85-0.9	8
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.6583	Remote Similarity	NPC205255
0.6588	Remote Similarity	NPC470483
0.6589	Remote Similarity	NPC204580
0.6591	Remote Similarity	NPC329567
0.6591	Remote Similarity	NPC210828

Showing 1 to 5 of 200 entries

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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 NPC133156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	746
0.2-0.3	871
0.3-0.4	1611
0.4-0.5	3112
0.5-0.6	2190
0.6-0.7	374
0.7-0.8	24
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
0.6286	Remote Similarity	NPD5030	Phase 2
0.6295	Remote Similarity	NPD2916	Discontinued
0.63	Remote Similarity	NPD4455	Discontinued
0.6305	Remote Similarity	NPD8091	Phase 3
0.6306	Remote Similarity	NPD6644	Discontinued

Showing 1 to 5 of 200 entries

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Structure

CID133156 OpenBabel06191715492D 29 31 0 0 0 0 0 0 0 0999 V2000 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -3.4641 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 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 1.7321 0.0000 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 1.5000 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 -1.7321 2.0000 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 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 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 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 25 1 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 15 20 2 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10385901
ChEMBL	CHEMBL464846
ZINC

Physicochemical Properties

Molecular Weight:	393.19
ALogP:	2.2256
MLogP:	3.55
XLogP:	3.808
# Rotatable Bonds:	12
Polar Surface Area:	81
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	29

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