NPASS Natural Product

Natural Product: NPC111422

Natural Product ID:	NPC111422
Common Name:	Beta,Beta-Dimethylacrylalkannin
IUPAC Name:	[(1S)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
Synonyms:
Molecular Formula:	C21H22O6
Standard InCHIKey:	BATBOVZTQBLKIL-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3/t17-/m0/s1
Canonical SMILES:	CC(=CC[C@@H](C1=CC(=O)c2c(C1=O)c(O)ccc2O)OC(=O)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	Reference
NPO11300	Eucalyptus coccifera	Species	Myrtaceae	Eukaryota	UNPD*
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	PMID[12502328]
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	TCM_Taiwan*
NPO11421	Arnebia euchroma	Species	Boraginaceae	Eukaryota	UNPD*
NPO11776	Lithospermum erythrorhizon	Species	Boraginaceae	Eukaryota	TCMSP*
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	PMID[20405844]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	TCM_Taiwan*
NPO26982	Callyspongia siphonella	Species	Callyspongiidae	Eukaryota	UNPD*
NPO30958	Onosma paniculatum	Species	Boraginaceae	Eukaryota	TCM_Taiwan*
NPO9209	Rhizomnium magnifolium	Species	Mniaceae	Eukaryota	UNPD*

Showing 1 to 10 of 10 entries

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Biological Activity

Activity Type	# Activity
IC50	14
MIC	5
Others	13

Activity Type	# Activity
Cell Line	16
Organism	15
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	680	nM	20405844
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	800	nM	20405844
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MBC	=	3.13	ug/ml	12502328
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	3.13	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	=	3.13	ug/ml	12502328
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.56	ug/ml	12502328
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	1.56	ug/ml	12502328
NPT165	Cell Line	HeLa	Homo sapiens	CD50	=	1.8	ug/ml	12502328

Showing 1 to 10 of 27 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 NPC111422 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	219
0.1-0.2	923
0.2-0.3	1843
0.3-0.4	3888
0.4-0.5	7279
0.5-0.6	5327
0.6-0.7	5535
0.7-0.8	5373
0.8-0.85	423
0.85-0.9	51
0.9-0.95	7
0.95-1	21

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Similarity Score	Similarity Level	Natural Product ID
0.8289	Intermediate Similarity	NPC137301
0.8296	Intermediate Similarity	NPC46634
0.8298	Intermediate Similarity	NPC115458
0.8298	Intermediate Similarity	NPC254603
0.8298	Intermediate Similarity	NPC193169

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 NPC111422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	812
0.2-0.3	1424
0.3-0.4	2315
0.4-0.5	2315
0.5-0.6	1352
0.6-0.7	547
0.7-0.8	161
0.8-0.85	9
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
0.6913	Remote Similarity	NPD2861	Phase 2
0.6919	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD6651	Approved
0.6937	Remote Similarity	NPD1512	Approved
0.6939	Remote Similarity	NPD6696	Suspended

Showing 1 to 5 of 200 entries

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Structure

CID111422 OpenBabel06191715462D 27 28 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 2.5981 3.5000 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 -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 1.7321 -1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 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 -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 1.7321 0.0000 0.0000 C 0 0 1 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 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 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 3.4641 2.0000 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 2.5981 0.5000 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 1 0 0 0 0 4 12 1 0 0 0 0 5 8 1 0 0 0 0 5 11 2 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 8 1 1 0 0 0 17 27 1 0 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 26 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	442720
ChEMBL	CHEMBL513640
ZINC

Physicochemical Properties

Molecular Weight:	370.14
ALogP:	1.8371
MLogP:	3.11
XLogP:	2.047
# Rotatable Bonds:	12
Polar Surface Area:	100.9
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	27

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