NPASS Natural Product

Natural Product: NPC178851

Natural Product ID:	NPC178851
Common Name:	Torachrysone 8-O-Glucoside
IUPAC Name:	1-[1-hydroxy-6-methoxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynaphthalen-2-yl]ethanone
Synonyms:	Torachrysone 8-O-Glucoside
Molecular Formula:	C20H24O9
Standard InCHIKey:	GHKWPHRULCFTBB-CZNQJBLBSA-N
Standard InCHI:	InChI=1S/C20H24O9/c1-8-4-10-5-11(27-3)6-12(15(10)17(24)14(8)9(2)22)28-20-19(26)18(25)16(23)13(7-21)29-20/h4-6,13,16,18-21,23-26H,7H2,1-3H3/t13-,16-,18+,19-,20-/m1/s1
Canonical SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc3c2c(O)c(c(c3)C)C(=O)C)[C@@H]([C@H]([C@@H]1O)O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	UNPD*
NPO10216	Leptocereus quadricostatus	Species	Cactaceae	Eukaryota	UNPD*
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	UNPD*
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	UNPD*
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	UNPD*
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	TM-MC*
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	UNPD*
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	UNPD*
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	UNPD*
NPO12108	Aizopsis selskiana	Species	Crassulaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	2
MIC	1

Activity Type	# Activity
Organism	2
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	18.5	ug/ml	12932135
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	69000	nM	10714491
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	8900	nM	22280816

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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 NPC178851 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	320
0.1-0.2	1184
0.2-0.3	2278
0.3-0.4	5076
0.4-0.5	6911
0.5-0.6	3874
0.6-0.7	3471
0.7-0.8	4189
0.8-0.85	2312
0.85-0.9	1123
0.9-0.95	136
0.95-1	15

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Similarity Score	Similarity Level	Natural Product ID
0.8944	High Similarity	NPC44931
0.8944	High Similarity	NPC65003
0.8951	High Similarity	NPC271270
0.8951	High Similarity	NPC153342
0.8951	High Similarity	NPC97285

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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 NPC178851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	876
0.2-0.3	1637
0.3-0.4	2579
0.4-0.5	1955
0.5-0.6	1121
0.6-0.7	441
0.7-0.8	160
0.8-0.85	42
0.85-0.9	16
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7063	Intermediate Similarity	NPD1283	Approved
0.7066	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1201	Approved
0.7089	Intermediate Similarity	NPD1610	Phase 2

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Structure

CID178851 OpenBabel06191715552D 29 31 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 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 4.3301 3.5000 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 4.3301 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 -1.7321 -0.0000 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 4.3301 -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 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 -0.8660 0.5000 0.0000 C 0 0 2 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 -0.8660 1.5000 0.0000 C 0 0 2 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 -0.0000 2.0000 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 2.5981 -1.5000 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 2.0000 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 1.7321 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 8 1 0 0 0 0 2 9 1 0 0 0 0 3 27 1 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 21 1 0 0 0 0 8 14 1 0 0 0 0 9 14 1 0 0 0 0 9 22 2 0 0 0 0 10 15 1 0 0 0 0 11 27 1 0 0 0 0 12 15 2 0 0 0 0 12 28 1 0 0 0 0 13 7 1 6 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 17 2 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 1 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 28 1 6 0 0 0 20 29 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11972479
ChEMBL	CHEMBL109330
ZINC

Physicochemical Properties

Molecular Weight:	408.14
ALogP:	-2.3312
MLogP:	2.67
XLogP:	0.815
# Rotatable Bonds:	13
Polar Surface Area:	145.91
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	29

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