NPASS Natural Product

Natural Product: NPC159750

Natural Product ID:	NPC159750
Common Name:	Uvarigrandin A
IUPAC Name:	(2S)-4-[(3S,13R)-3,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Uvarigrandin A
Molecular Formula:	C37H66O7
Standard InCHIKey:	SXPGOPRMCQROGB-WGCJABNLSA-N
Standard InCHI:	InChI=1S/C37H66O7/c1-3-4-5-6-7-10-13-16-19-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)20-17-14-11-8-9-12-15-18-30(38)22-21-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30-,31+,32+,33+,34+,35+,36+/m0/s1
Canonical SMILES:	CCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@@H](CCCCCCCCC[C@@H](CCC1=C[C@@H](OC1=O)C)O)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	Isolation Part	Collection Location	Collection Time	Reference
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds			PMID[22011319]

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Biological Activity

Activity Type	# Activity
IC50	7

Activity Type	# Activity
Cell Line	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1097	Cell Line	MKN-45	Homo sapiens	IC50	=	0.069	ug/ml	22011319
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	0.07	ug/ml	22011319
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.78	ug/ml	22011319
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	0.0029	ug/ml	22011319
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.08	ug/ml	22011319
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000	nM	25582602
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.096	ug/ml	22011319

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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 NPC159750 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	113
0.1-0.2	830
0.2-0.3	3550
0.3-0.4	7599
0.4-0.5	10278
0.5-0.6	5641
0.6-0.7	2356
0.7-0.8	362
0.8-0.85	18
0.85-0.9	31
0.9-0.95	80
0.95-1	31

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Similarity Score	Similarity Level	Natural Product ID
0.7674	Intermediate Similarity	NPC475711
0.7677	Intermediate Similarity	NPC86077
0.7692	Intermediate Similarity	NPC474949
0.7692	Intermediate Similarity	NPC475019
0.7708	Intermediate Similarity	NPC476315

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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 NPC159750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	1646
0.2-0.3	3881
0.3-0.4	2441
0.4-0.5	739
0.5-0.6	272
0.6-0.7	52
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5604	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8267	Approved
0.561	Remote Similarity	NPD5983	Phase 2
0.561	Remote Similarity	NPD8269	Approved
0.561	Remote Similarity	NPD29	Approved

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Structure

CID159750 OpenBabel06191715532D 44 46 0 0 1 0 0 0 0 0999 V2000 18.4410 -5.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 -1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1320 -4.1912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1538 -3.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4847 -4.7264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5065 -4.5185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8374 -5.2616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9904 1.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3212 0.5888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8593 -5.0537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9685 1.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3431 0.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1901 -5.7969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6376 1.8671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6740 0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2120 -5.5890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6158 1.6592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6958 0.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5428 -6.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9248 0.7082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -0.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3046 -4.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5158 -1.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3046 -3.8641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5158 -2.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0267 -0.4817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5647 -6.1242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -0.0350 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -5.1731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5647 -0.9860 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2557 -3.5551 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.5647 -2.6041 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3357 -1.4328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8956 -6.8673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2775 0.1729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 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 10.8435 -4.3641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9769 -1.7950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 34 1 0 0 0 0 27 28 1 0 0 0 0 27 29 2 0 0 0 0 28 2 1 6 0 0 0 28 42 1 0 0 0 0 29 37 1 0 0 0 0 30 38 1 6 0 0 0 31 39 1 1 0 0 0 32 40 1 6 0 0 0 33 31 1 1 0 0 0 33 43 1 0 0 0 0 34 32 1 1 0 0 0 34 44 1 0 0 0 0 35 25 1 6 0 0 0 35 36 1 0 0 0 0 35 43 1 0 0 0 0 36 26 1 6 0 0 0 36 44 1 0 0 0 0 37 41 2 0 0 0 0 37 42 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	9986397
ChEMBL	CHEMBL1933125
ZINC

Physicochemical Properties

Molecular Weight:	622.48
ALogP:	-8.3702
MLogP:	4.76
XLogP:	9.577
# Rotatable Bonds:	30
Polar Surface Area:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	44

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