NPASS Natural Product

Natural Product: NPC74410

Natural Product ID:	NPC74410
Common Name:	Callicarpic Acid B
IUPAC Name:	3-[(1S,2S)-1-methyl-5,8-dioxo-6-propan-2-yl-2-prop-1-en-2-yl-3,4-dihydro-2H-naphthalen-1-yl]propanoic acid
Synonyms:	Callicarpic Acid B
Molecular Formula:	C20H26O4
Standard InCHIKey:	GPJZKLLQWSDGSG-YWZLYKJASA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-11(2)14-10-16(21)18-13(19(14)24)6-7-15(12(3)4)20(18,5)9-8-17(22)23/h10-11,15H,3,6-9H2,1-2,4-5H3,(H,22,23)/t15-,20-/m0/s1
Canonical SMILES:	OC(=O)CC[C@@]1(C)[C@@H](CCC2=C1C(=O)C=C(C2=O)C(C)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	Isolation Part	Collection Location	Collection Time	Reference
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota				PMID[19193025]

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Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	63600	nM	19489598

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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 NPC74410 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	94
0.1-0.2	682
0.2-0.3	3503
0.3-0.4	9835
0.4-0.5	6927
0.5-0.6	4618
0.6-0.7	3605
0.7-0.8	1411
0.8-0.85	166
0.85-0.9	43
0.9-0.95	5
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC260474
0.8	Intermediate Similarity	NPC173089
0.8	Intermediate Similarity	NPC476253
0.8025	Intermediate Similarity	NPC477057
0.8025	Intermediate Similarity	NPC472478

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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 NPC74410 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	116
0.1-0.2	1309
0.2-0.3	3776
0.3-0.4	2628
0.4-0.5	792
0.5-0.6	234
0.6-0.7	189
0.7-0.8	109
0.8-0.85	8
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
0.6486	Remote Similarity	NPD3195	Phase 2
0.6486	Remote Similarity	NPD3194	Approved
0.6486	Remote Similarity	NPD3196	Approved
0.6512	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6335	Approved

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Structure

NPC74410 OpenBabel07101719142D 24 25 0 0 1 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 4.3301 1.5000 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 -2.5981 0.5000 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 0.0000 2.0000 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 -0.0000 -1.7321 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 2.5981 0.5000 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 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 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 1 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 -0.5000 -2.5981 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 -0.0000 0.0000 C 0 0 2 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 -1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.4641 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 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 6 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 24 2 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	25227580
ChEMBL	CHEMBL559707
ZINC

Physicochemical Properties

Molecular Weight:	330.18
ALogP:	1.758
MLogP:	3.22
XLogP:	2.82
# Rotatable Bonds:	10
Polar Surface Area:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	24

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