NPASS Natural Product

Natural Product: NPC248793

Natural Product ID:	NPC248793
Common Name:	Mundulinol
IUPAC Name:	(7R,8R)-5,7-dihydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)-8-phenyl-7,8-dihydropyrano[3,2-g]chromen-6-one
Synonyms:	Mundulinol
Molecular Formula:	C25H26O5
Standard InCHIKey:	UNYRLLNPZQFKTP-FCHUYYIVSA-N
Standard InCHI:	InChI=1S/C25H26O5/c1-14(2)10-11-17-23-16(12-13-25(3,4)30-23)19(26)18-20(27)21(28)22(29-24(17)18)15-8-6-5-7-9-15/h5-10,12-13,21-22,26,28H,11H2,1-4H3/t21-,22+/m0/s1
Canonical SMILES:	CC(=CCc1c2O[C@H](c3ccccc3)[C@H](C(=O)c2c(c2c1OC(C)(C)C=C2)O)O)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
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	bark	an elevation of 850 m (17�17�25�?'S; 48�40�30�?� E), Toamasina, Madagascar	2002-JAN	PMID[15043430]
NPO11029	Bessera tenuiflora	Species	Asparagaceae	Eukaryota				UNPD*
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota				UNPD*
NPO14464	Oxalis triangularis	Species	Oxalidaceae	Eukaryota				UNPD*
NPO14502	Pogonolepis muelleriana	Species	Asteraceae	Eukaryota				UNPD*
NPO16240	Dunbaria longiracemosa	Species	Fabaceae	Eukaryota				UNPD*
NPO24957	Terminalia buceras	Species	Combretaceae	Eukaryota				UNPD*
NPO28113	Oria flava	NA	NA	NA				UNPD*
NPO28183	Cymbopogon flexuosus	Species	Poaceae	Eukaryota				UNPD*
NPO28235	Heimia montana	Species	Lythraceae	Eukaryota				UNPD*

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Biological Activity

Activity Type	# Activity
IC50	10

Activity Type	# Activity
Cell Line	8
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	8.5	ug/ml	12542360
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	25	ug/ml	15043430
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	7	ug/ml	12542360
NPT2	Others	Unspecified		IC50	=	7.5	ug/ml	12542360
NPT2	Others	Unspecified		IC50	=	13	ug/ml	12542360
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	9.3	ug/ml	12542360
NPT309	Cell Line	1A9	Homo sapiens	IC50	=	8.2	ug/ml	12542360
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7.5	ug/ml	12542360
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7.5	ug/ml	12542360
NPT91	Cell Line	KB	Homo sapiens	IC50	=	8.5	ug/ml	12542360

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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 NPC248793 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	276
0.1-0.2	1057
0.2-0.3	2175
0.3-0.4	5105
0.4-0.5	7573
0.5-0.6	3407
0.6-0.7	3829
0.7-0.8	3960
0.8-0.85	1486
0.85-0.9	1510
0.9-0.95	453
0.95-1	58

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Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC219915
0.9252	High Similarity	NPC9117
0.9252	High Similarity	NPC212932
0.9252	High Similarity	NPC112749
0.9252	High Similarity	NPC478086

Showing 1 to 5 of 200 entries

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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 NPC248793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	819
0.2-0.3	1523
0.3-0.4	2524
0.4-0.5	2099
0.5-0.6	1196
0.6-0.7	481
0.7-0.8	184
0.8-0.85	23
0.85-0.9	21
0.9-0.95	8
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7118	Intermediate Similarity	NPD37	Approved
0.7119	Intermediate Similarity	NPD7228	Approved
0.712	Intermediate Similarity	NPD8319	Approved
0.712	Intermediate Similarity	NPD8320	Phase 1
0.7125	Intermediate Similarity	NPD4538	Approved

Showing 1 to 5 of 200 entries

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Structure

CID248793 OpenBabel06191716052D 30 33 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 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 6.0622 -1.5000 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 5.1962 -1.0000 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 2.5981 -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 0.0000 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 2.5981 -2.5000 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 0.8660 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 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 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 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 25 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 2 0 0 0 0 21 22 1 0 0 0 0 21 28 1 6 0 0 0 22 15 1 1 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10363971
ChEMBL	CHEMBL491693
ZINC

Physicochemical Properties

Molecular Weight:	406.18
ALogP:	1.2392
MLogP:	3.66
XLogP:	5.028
# Rotatable Bonds:	9
Polar Surface Area:	75.99
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	30

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