NPASS Natural Product

Natural Product: NPC277369

Natural Product ID:	NPC277369
Common Name:	(S)-7,9-Dimethoxy-3-Methyl-3,4-Dihydro-1H-Benzo[G]Isochromene-5,10-Dione
IUPAC Name:	(3S)-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione
Synonyms:
Molecular Formula:	C16H16O5
Standard InCHIKey:	XOHGULAZSZLZHM-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C16H16O5/c1-8-4-10-12(7-21-8)16(18)14-11(15(10)17)5-9(19-2)6-13(14)20-3/h5-6,8H,4,7H2,1-3H3/t8-/m0/s1
Canonical SMILES:	COc1cc(OC)c2c(c1)C(=O)C1=C(C2=O)CO[C@H](C1)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO2140	Botryococcus braunii	Species	Botryococcaceae	Eukaryota	UNPD*
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	UNPD*
NPO3035	Karwinskia humboldtiana	Species	Rhamnaceae	Eukaryota	UNPD*
NPO7706	Bartlettina karwinskiana	Species	Asteraceae	Eukaryota	UNPD*
NPO9402	Morus mongolica	Species	Moraceae	Eukaryota	UNPD*
NPO9708	Aster verticillatus	Species	Asteraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
EC50	3

Activity Type	# Activity
Cell Line	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	EC50	=	4460	nM	24436995
NPT82	Cell Line	MDA-MB-231	Homo sapiens	EC50	=	12845	nM	24436995
NPT82	Cell Line	MDA-MB-231	Homo sapiens	EC50	=	18035	nM	24436995

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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 NPC277369 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	323
0.1-0.2	1261
0.2-0.3	2290
0.3-0.4	5287
0.4-0.5	7651
0.5-0.6	3098
0.6-0.7	4467
0.7-0.8	4505
0.8-0.85	1743
0.85-0.9	248
0.9-0.95	14
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.8561	High Similarity	NPC473894
0.8561	High Similarity	NPC211120
0.8562	High Similarity	NPC94076
0.8562	High Similarity	NPC469404
0.8562	High Similarity	NPC474385

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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 NPC277369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	960
0.2-0.3	1528
0.3-0.4	2560
0.4-0.5	1995
0.5-0.6	1160
0.6-0.7	437
0.7-0.8	161
0.8-0.85	28
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6959	Remote Similarity	NPD1608	Approved
0.6959	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD9545	Approved
0.697	Remote Similarity	NPD5890	Approved
0.697	Remote Similarity	NPD5889	Approved

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Structure

CID277369 OpenBabel06191716082D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 2.5981 1.5000 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 1.7321 -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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 -2.0000 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 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 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 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 8 1 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 12 1 0 0 0 0 7 21 1 0 0 0 0 8 1 1 6 0 0 0 8 21 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	45257195
ChEMBL	CHEMBL609285
ZINC

Physicochemical Properties

Molecular Weight:	288.10
ALogP:	-0.6338
MLogP:	2.67
XLogP:	0.574
# Rotatable Bonds:	5
Polar Surface Area:	61.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	21

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