NPASS Natural Product

Natural Product: NPC81679

Natural Product ID:	NPC81679
Common Name:	Brandisianin B
IUPAC Name:	(8R)-5-hydroxy-3-(4-hydroxy-2,5-dimethoxyphenyl)-8-prop-1-en-2-yl-8,9-dihydrofuro[2,3-h]chromen-4-one
Synonyms:
Molecular Formula:	C22H20O7
Standard InCHIKey:	VIMHZMOJYABXJB-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C22H20O7/c1-10(2)16-6-12-18(29-16)8-15(24)20-21(25)13(9-28-22(12)20)11-5-19(27-4)14(23)7-17(11)26-3/h5,7-9,16,23-24H,1,6H2,2-4H3/t16-/m1/s1
Canonical SMILES:	COc1cc(O)c(cc1c1coc2c(c1=O)c(O)cc1c2C[C@@H](O1)C(=C)C)OC
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
NPO24609	Millettia brandisiana	Species	Fabaceae	Eukaryota				PMID[18039011]

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	9700	nM	18955526
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	25000	nM	18955526

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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 NPC81679 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	318
0.1-0.2	1195
0.2-0.3	2426
0.3-0.4	5887
0.4-0.5	7089
0.5-0.6	2737
0.6-0.7	3225
0.7-0.8	4257
0.8-0.85	1801
0.85-0.9	1270
0.9-0.95	664
0.95-1	20

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Similarity Score	Similarity Level	Natural Product ID
0.9304	High Similarity	NPC61010
0.9304	High Similarity	NPC40491
0.9304	High Similarity	NPC26326
0.9304	High Similarity	NPC474186
0.9308	High Similarity	NPC7483

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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 NPC81679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	857
0.2-0.3	1695
0.3-0.4	2590
0.4-0.5	1952
0.5-0.6	1061
0.6-0.7	485
0.7-0.8	148
0.8-0.85	34
0.85-0.9	15
0.9-0.95	6
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7006	Intermediate Similarity	NPD1610	Phase 2
0.701	Intermediate Similarity	NPD4111	Phase 1
0.701	Intermediate Similarity	NPD4665	Approved
0.7012	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6355	Discontinued

Showing 1 to 5 of 200 entries

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Structure

NPC81679 OpenBabel07101718322D 29 32 0 0 1 0 0 0 0 0999 V2000 3.9049 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9049 2.8660 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 -6.0622 -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 1.8171 1.1910 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 0.0000 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 3.4049 2.0000 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 0.8660 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 -4.3301 -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 2.4049 2.0000 0.0000 C 0 0 2 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 2.5000 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 -0.8660 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -2.5981 1.5000 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 -5.1962 0.0000 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 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 10 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 11 2 0 0 0 0 5 19 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 14 1 0 0 0 0 7 17 2 0 0 0 0 8 15 2 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 28 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 15 24 1 0 0 0 0 16 10 1 1 0 0 0 16 29 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 25 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24763481
ChEMBL	CHEMBL251258
ZINC

Physicochemical Properties

Molecular Weight:	396.12
ALogP:	-0.6791
MLogP:	3.11
XLogP:	1.549
# Rotatable Bonds:	9
Polar Surface Area:	94.45
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	29

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