NPASS Natural Product

Natural Product: NPC188814

Natural Product ID:	NPC188814
Common Name:	Malabaricone A
IUPAC Name:	1-(2,6-dihydroxyphenyl)-9-phenylnonan-1-one
Synonyms:	Malabaricone A
Molecular Formula:	C21H26O3
Standard InCHIKey:	IAXIHKJASWPASP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H26O3/c22-18(21-19(23)15-10-16-20(21)24)14-9-4-2-1-3-6-11-17-12-7-5-8-13-17/h5,7-8,10,12-13,15-16,23-24H,1-4,6,9,11,14H2
Canonical SMILES:	O=C(c1c(O)cccc1O)CCCCCCCCc1ccccc1
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
NPO14474	Klasea sogdiana	Species	Asteraceae	Eukaryota				UNPD*
NPO8263	Asclepias vestita	Species	Apocynaceae	Eukaryota				UNPD*

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Biological Activity

Activity Type	# Activity
IC50	2
MIC	1
Others	5

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Organism	1
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	25	ug/ml	22280816
NPT2	Others	Unspecified		Ratio IC50	=	32.95		27236720
NPT2	Others	Unspecified		Ratio IC50	=	0.04		27236720
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	1310	nM	27236720
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	97.42	%	27236720
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	39210	nM	27236720
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	69.55	%	27236720
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	12	%	20805034

Showing 1 to 8 of 8 entries

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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 NPC188814 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	221
0.1-0.2	1104
0.2-0.3	2380
0.3-0.4	7243
0.4-0.5	6618
0.5-0.6	3498
0.6-0.7	5710
0.7-0.8	3409
0.8-0.85	554
0.85-0.9	109
0.9-0.95	40
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8361	Intermediate Similarity	NPC292665
0.8362	Intermediate Similarity	NPC116842
0.8372	Intermediate Similarity	NPC128216
0.8372	Intermediate Similarity	NPC267205
0.8374	Intermediate Similarity	NPC283514

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 NPC188814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	941
0.2-0.3	1129
0.3-0.4	2511
0.4-0.5	2444
0.5-0.6	1306
0.6-0.7	454
0.7-0.8	109
0.8-0.85	16
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6694	Remote Similarity	NPD5909	Discontinued
0.6694	Remote Similarity	NPD9273	Approved
0.6713	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD9279	Approved
0.6733	Remote Similarity	NPD6980	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID188814 OpenBabel06191715572D 24 25 0 0 0 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 1.7321 -0.0000 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 -5.1962 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 0.8660 -0.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 17 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	324062
ChEMBL	CHEMBL1254269
ZINC

Physicochemical Properties

Molecular Weight:	326.19
ALogP:	-2.8152
MLogP:	3.44
XLogP:	8.373
# Rotatable Bonds:	12
Polar Surface Area:	57.53
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	24

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