NPASS Natural Product

Natural Product: NPC470402

Natural Product ID:	NPC470402
Common Name:	Amyrisin B
IUPAC Name:	5,7-dihydroxy-2-[4-(2-hydroxy-3-methylbut-3-enoxy)phenyl]-6-methoxychromen-4-one
Synonyms:	Amyrisin B
Molecular Formula:	C21H20O7
Standard InCHIKey:	RSFSMBFMVJOURC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O7/c1-11(2)16(24)10-27-13-6-4-12(5-7-13)17-8-14(22)19-18(28-17)9-15(23)21(26-3)20(19)25/h4-9,16,23-25H,1,10H2,2-3H3
Canonical SMILES:	COc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)OCC(C(=C)C)O
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
NPO1170	Amyris madrensis	Species	Rutaceae	Eukaryota				PMID[22260294]

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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
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	17500	nM	17889536
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	17500	nM	25008455

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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 NPC470402 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	297
0.1-0.2	1182
0.2-0.3	2502
0.3-0.4	6254
0.4-0.5	6795
0.5-0.6	2539
0.6-0.7	3283
0.7-0.8	4152
0.8-0.85	1798
0.85-0.9	1229
0.9-0.95	714
0.95-1	144

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Similarity Score	Similarity Level	Natural Product ID
0.943	High Similarity	NPC201292
0.943	High Similarity	NPC186807
0.943	High Similarity	NPC226294
0.943	High Similarity	NPC93337
0.943	High Similarity	NPC105025

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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 NPC470402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	853
0.2-0.3	1707
0.3-0.4	2619
0.4-0.5	1871
0.5-0.6	1048
0.6-0.7	545
0.7-0.8	149
0.8-0.85	30
0.85-0.9	13
0.9-0.95	12
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7032	Intermediate Similarity	NPD1608	Approved
0.7033	Intermediate Similarity	NPD7240	Approved
0.7051	Intermediate Similarity	NPD3225	Approved
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7062	Intermediate Similarity	NPD7229	Phase 3

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Structure

NPC470402 OpenBabel07101718302D 28 30 0 0 1 0 0 0 0 0999 V2000 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 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 6.0622 2.5000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 3 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 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 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 11 2 0 0 0 0 2 11 1 0 0 0 0 3 26 1 0 0 0 0 4 6 1 0 0 0 0 4 12 2 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 8 17 2 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 27 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 22 2 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 28 1 0 0 0 0 18 19 2 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	57381727
ChEMBL	CHEMBL2023532
ZINC

Physicochemical Properties

Molecular Weight:	384.12
ALogP:	-0.9753
MLogP:	3
XLogP:	1.502
# Rotatable Bonds:	11
Polar Surface Area:	105.45
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	28

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