NPASS Natural Product

Natural Product: NPC78492

Natural Product ID:	NPC78492
Common Name:	8-[(E)-4-Phenylprop-2-En-1-One]-(2S,3R)-2-(3,5-Dihydroxyphenyl)-3,4-Dihydro-2H-2-Benzopyran-5-Methoxyl-3,7-Diol
IUPAC Name:	(E)-1-[(2S,3R)-2-(3,5-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-3,4-dihydro-2H-chromen-8-yl]-3-phenylprop-2-en-1-one
Synonyms:
Molecular Formula:	C25H22O7
Standard InCHIKey:	BARBUPBDCQNXQJ-BXDPLHIOSA-N
Standard InCHI:	InChI=1S/C25H22O7/c1-31-22-13-20(29)23(19(28)8-7-14-5-3-2-4-6-14)25-18(22)12-21(30)24(32-25)15-9-16(26)11-17(27)10-15/h2-11,13,21,24,26-27,29-30H,12H2,1H3/b8-7+/t21-,24+/m1/s1
Canonical SMILES:	COc1cc(O)c(c2c1C[C@@H](O)[C@@H](O2)c1cc(O)cc(c1)O)C(=O)/C=C/c1ccccc1
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
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota		China		PMID[19278239]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

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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	=	7100	nM	9051909

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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 NPC78492 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	1108
0.2-0.3	2175
0.3-0.4	5211
0.4-0.5	7489
0.5-0.6	3004
0.6-0.7	3212
0.7-0.8	4316
0.8-0.85	1637
0.85-0.9	1861
0.9-0.95	556
0.95-1	24

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Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC23728
0.92	High Similarity	NPC476182
0.92	High Similarity	NPC176869
0.92	High Similarity	NPC110303
0.92	High Similarity	NPC122828

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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 NPC78492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	843
0.2-0.3	1511
0.3-0.4	2461
0.4-0.5	2062
0.5-0.6	1162
0.6-0.7	556
0.7-0.8	206
0.8-0.85	22
0.85-0.9	30
0.9-0.95	9
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7261	Intermediate Similarity	NPD3268	Approved
0.7261	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7268	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD1470	Approved

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Structure

NPC78492 OpenBabel07101718202D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.3301 -0.5000 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 4.3301 -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 3.4641 -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 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -2.5981 -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 0.8660 1.5000 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 2.5981 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 0.0000 -2.0000 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 2 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 -0.0000 1.0000 0.0000 C 0 0 1 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 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 28 2 0 0 0 0 20 23 1 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 31 1 0 0 0 0 23 25 2 0 0 0 0 24 15 1 6 0 0 0 24 32 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	42638983
ChEMBL	CHEMBL561568
ZINC

Physicochemical Properties

Molecular Weight:	434.14
ALogP:	-1.9882
MLogP:	3.44
XLogP:	4.408
# Rotatable Bonds:	10
Polar Surface Area:	116.45
# H-Bond Aceptor:	2
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	32

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