NPASS Natural Product

Natural Product: NPC261004

Natural Product ID:	NPC261004
Common Name:	Chrysosplenol B
IUPAC Name:	5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6,7-trimethoxychromen-4-one
Synonyms:
Molecular Formula:	C19H18O8
Standard InCHIKey:	NBVTYGIYKCPHQN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O8/c1-23-11-7-9(5-6-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
Canonical SMILES:	COc1cc2oc(c3ccc(c(c3)OC)O)c(c(=O)c2c(c1OC)O)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10235	Castanopsis eyrei	Species	Fagaceae	Eukaryota	UNPD*
NPO10250	Alectoria rigida	Species	Parmeliaceae	Eukaryota	UNPD*
NPO103	Stereocaulon salazinum	Species	Stereocaulaceae	Eukaryota	UNPD*
NPO1040	Ficus conraui	Species	Moraceae	Eukaryota	UNPD*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	TCMID*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	TM-MC*
NPO11028	Melanoleuca grammopodia	Species	Tricholomataceae	Eukaryota	UNPD*
NPO11665	Kloeckera brevis	NA	NA	NA	UNPD*
NPO12656	Holarrhena febrifuga	Species	Apocynaceae	Eukaryota	UNPD*
NPO1270	Potamogeton malaianus	Species	Potamogetonaceae	Eukaryota	UNPD*

Showing 1 to 10 of 57 entries

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Biological Activity

Activity Type	# Activity
EC50	9
ED50	1
GI50	1
IC50	3

Activity Type	# Activity
Cell Line	14

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	14200	nM	8182705
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	79000	nM	8182705
NPT168	Cell Line	P388	Mus musculus	EC50	>	20	ug/ml	8182705
NPT517	Cell Line	Panel NCI-60 (60 carcinoma cell lines)	Homo sapiens	GI50	>	33000	nM	9632366
NPT762	Cell Line	A-431	Homo sapiens	EC50	>	20	ug/ml	8182705
NPT91	Cell Line	KB	Homo sapiens	EC50	>	20	ug/ml	8182705
NPT91	Cell Line	KB	Homo sapiens	EC50	=	0.8	ug/ml	8182705
NPT91	Cell Line	KB	Homo sapiens	ED50	=	7.42	ug/ml	1955888
NPT929	Cell Line	BC1 cell line		EC50	>	20	ug/ml	8182705
NPT930	Cell Line	Fibrosarcoma cell line		EC50	=	4.2	ug/ml	8182705

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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 NPC261004 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	333
0.1-0.2	1282
0.2-0.3	3013
0.3-0.4	6987
0.4-0.5	5694
0.5-0.6	2582
0.6-0.7	3567
0.7-0.8	4026
0.8-0.85	1745
0.85-0.9	974
0.9-0.95	530
0.95-1	156

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Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC471479
0.9416	High Similarity	NPC78225
0.9416	High Similarity	NPC474836
0.9416	High Similarity	NPC472910
0.9416	High Similarity	NPC471515

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 NPC261004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	898
0.2-0.3	1745
0.3-0.4	2667
0.4-0.5	1817
0.5-0.6	1038
0.6-0.7	468
0.7-0.8	135
0.8-0.85	27
0.85-0.9	13
0.9-0.95	9
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6935	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7801	Approved
0.6941	Remote Similarity	NPD3146	Approved
0.6941	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3688	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID261004 OpenBabel06191716062D 27 29 0 0 0 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 -4.3301 0.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -1.7321 -0.0000 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 3.4641 -1.0000 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 -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 -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 0.8660 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 2.5981 -2.5000 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 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281608
ChEMBL	CHEMBL33256
ZINC

Physicochemical Properties

Molecular Weight:	374.10
ALogP:	-1.9715
MLogP:	2.67
XLogP:	1.438
# Rotatable Bonds:	11
Polar Surface Area:	103.68
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	27

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