NPASS Natural Product

Natural Product: NPC166757

Natural Product ID:	NPC166757
Common Name:	Citrusinol
IUPAC Name:	3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethylpyrano[2,3-h]chromen-4-one
Synonyms:	Citrusinol
Molecular Formula:	C20H16O6
Standard InCHIKey:	OKQQXHUICMLKQI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O6/c1-20(2)8-7-12-14(26-20)9-13(22)15-16(23)17(24)18(25-19(12)15)10-3-5-11(21)6-4-10/h3-9,21-22,24H,1-2H3
Canonical SMILES:	Oc1ccc(cc1)c1oc2c3C=CC(Oc3cc(c2c(=O)c1O)O)(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	Isolation Part	Collection Location	Collection Time	Reference
NPO17807	Dysosma versipellis	Species	Berberidaceae	Eukaryota				TCMID*

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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
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	43300	nM	15921433
NPT91	Cell Line	KB	Homo sapiens	IC50	=	42300	nM	15921433

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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 NPC166757 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	296
0.1-0.2	1289
0.2-0.3	2445
0.3-0.4	6355
0.4-0.5	6781
0.5-0.6	2629
0.6-0.7	4349
0.7-0.8	3607
0.8-0.85	1488
0.85-0.9	1107
0.9-0.95	491
0.95-1	52

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Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC7989
0.92	High Similarity	NPC192587
0.92	High Similarity	NPC276444
0.92	High Similarity	NPC471985
0.9205	High Similarity	NPC264932

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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 NPC166757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	931
0.2-0.3	1415
0.3-0.4	2480
0.4-0.5	2106
0.5-0.6	1227
0.6-0.7	468
0.7-0.8	154
0.8-0.85	35
0.85-0.9	21
0.9-0.95	1
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7055	Intermediate Similarity	NPD7447	Phase 1
0.7074	Intermediate Similarity	NPD7870	Phase 2
0.7074	Intermediate Similarity	NPD7871	Phase 2
0.7078	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3887	Approved

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Structure

CID166757 OpenBabel06191715542D 26 29 0 0 0 0 0 0 0 0999 V2000 0.2588 1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7934 0.3912 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 -1.7321 1.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -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 -3.4641 -2.0000 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 -4.3301 -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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 -3.4641 -3.0000 0.0000 O 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 -3.4641 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44259051
ChEMBL	CHEMBL463744
ZINC

Physicochemical Properties

Molecular Weight:	352.09
ALogP:	-0.9728
MLogP:	3
XLogP:	3.315
# Rotatable Bonds:	6
Polar Surface Area:	96.22
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	26

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