NPASS Natural Product

Natural Product: NPC110609

Natural Product ID:	NPC110609
Common Name:	Alkannin
IUPAC Name:	5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
Synonyms:	E103
Molecular Formula:	C16H16O5
Standard InCHIKey:	NEZONWMXZKDMKF-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1
Canonical SMILES:	CC(=CC[C@@H](C1=CC(=O)c2c(C1=O)c(O)ccc2O)O)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
NPO11300	Eucalyptus coccifera	Species	Myrtaceae	Eukaryota	UNPD*
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	TCM_Taiwan*
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	PMID[12502328]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	UNPD*
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	TM-MC*
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	TM-MC*
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	PMID[20405844]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	TM-MC*
NPO24872	Arnebia nobilis	Species	Boraginaceae	Eukaryota	TCM_Taiwan*
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	18
MIC	6
Others	18

Activity Type	# Activity
Cell Line	19
Individual Protein	1
Organism	19
Others	2
Uncleic Acid	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1300	nM	25127868
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	780	nM	20405844
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	4030	nM	20405844
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	MIC	=	500000	nM	9873739
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MBC	=	50	ug/ml	12502328
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	50	ug/ml	12502328
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	Ratio	<=	2		12502328
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Ratio	<=	2		12502328
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	12.5	ug/ml	12502328
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug/ml	12502328

Showing 1 to 10 of 37 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 NPC110609 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	205
0.1-0.2	962
0.2-0.3	1795
0.3-0.4	4341
0.4-0.5	8511
0.5-0.6	4487
0.6-0.7	6706
0.7-0.8	3518
0.8-0.85	252
0.85-0.9	80
0.9-0.95	29
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8214	Intermediate Similarity	NPC53414
0.8214	Intermediate Similarity	NPC471905
0.8219	Intermediate Similarity	NPC112816
0.8227	Intermediate Similarity	NPC162939
0.8231	Intermediate Similarity	NPC315520

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 NPC110609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	852
0.2-0.3	1365
0.3-0.4	2425
0.4-0.5	2413
0.5-0.6	1260
0.6-0.7	520
0.7-0.8	95
0.8-0.85	1
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
0.6692	Remote Similarity	NPD3020	Approved
0.6693	Remote Similarity	NPD845	Approved
0.6703	Remote Similarity	NPD7701	Phase 2
0.6706	Remote Similarity	NPD7074	Phase 3
0.6706	Remote Similarity	NPD4956	Approved

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Structure

CID110609 OpenBabel06191715462D 21 22 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 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 -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 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 -0.8660 -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 -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 1 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 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 0.8660 -0.5000 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 1.0000 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 1.7321 1.0000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 8 1 0 0 0 0 3 4 1 0 0 0 0 3 8 2 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 6 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	72521
ChEMBL	CHEMBL28457
ZINC

Physicochemical Properties

Molecular Weight:	288.10
ALogP:	0.0184
MLogP:	2.67
XLogP:	0.858
# Rotatable Bonds:	8
Polar Surface Area:	94.83
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	21

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