NPASS Natural Product

Natural Product: NPC120390

Natural Product ID:	NPC120390
Common Name:	Madagascarensilide A
IUPAC Name:	3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,3R,4R,5S,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:	Madagascarensilide A
Molecular Formula:	C42H66O16
Standard InCHIKey:	WJHPUABOKULIAF-NJEWETTNSA-N
Standard InCHI:	InChI=1S/C42H66O16/c1-19-35(57-39-34(49)37(51-5)36(20(2)54-39)58-38-33(48)32(47)31(46)28(17-43)56-38)27(44)16-30(53-19)55-23-8-11-40(3)22(15-23)6-7-26-25(40)9-12-41(4)24(10-13-42(26,41)50)21-14-29(45)52-18-21/h14,19-20,22-28,30-39,43-44,46-50H,6-13,15-18H2,1-5H3/t19-,20-,22-,23+,24-,25+,26-,27+,28-,30+,31-,32+,33-,34-,35-,36+,37-,38+,39+,40+,41-,42+/m1/s1
Canonical SMILES:	CO[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H](O)C[C@@H](O[C@@H]2C)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C)O[C@@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)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
NPO33348	leptadenia madagascariensis	Species	Apocynaceae	Eukaryota		Madagascar dry forest		PMID[21159516]

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	180	nM	17567121
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	160	nM	7996553

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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 NPC120390 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	178
0.1-0.2	1124
0.2-0.3	3154
0.3-0.4	6229
0.4-0.5	8926
0.5-0.6	5391
0.6-0.7	3502
0.7-0.8	1665
0.8-0.85	466
0.85-0.9	166
0.9-0.95	54
0.95-1	34

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Similarity Score	Similarity Level	Natural Product ID
0.8618	High Similarity	NPC251866
0.8618	High Similarity	NPC469752
0.8618	High Similarity	NPC471359
0.8618	High Similarity	NPC180079
0.8618	High Similarity	NPC469754

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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 NPC120390 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1498
0.2-0.3	3950
0.3-0.4	2400
0.4-0.5	633
0.5-0.6	310
0.6-0.7	141
0.7-0.8	31
0.8-0.85	0
0.85-0.9	4
0.9-0.95	3
0.95-1	8

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5931	Remote Similarity	NPD7260	Phase 2
0.5932	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD3669	Approved
0.5935	Remote Similarity	NPD5284	Approved
0.5935	Remote Similarity	NPD5281	Approved

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Structure

NPC120390 OpenBabel07101718182D 58 65 0 0 1 0 0 0 0 0999 V2000 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 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 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -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 4.3301 -0.5000 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 -1.5388 0.5000 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 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 2.5691 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6723 3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3923 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2111 3.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.1244 -5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9904 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.9904 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2583 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2583 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.1244 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0201 4.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 3.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 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 11.2583 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 41 1 0 0 0 0 5 51 1 0 0 0 0 6 7 1 0 0 0 0 6 22 1 0 0 0 0 7 26 1 0 0 0 0 8 11 1 0 0 0 0 8 23 1 0 0 0 0 9 12 1 0 0 0 0 9 25 1 0 0 0 0 10 13 1 0 0 0 0 10 24 1 0 0 0 0 11 40 1 0 0 0 0 12 41 1 0 0 0 0 13 42 1 0 0 0 0 14 21 2 0 0 0 0 14 29 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 27 1 0 0 0 0 16 30 1 0 0 0 0 17 43 1 0 0 0 0 18 21 1 0 0 0 0 18 52 1 0 0 0 0 19 1 1 6 0 0 0 19 35 1 0 0 0 0 19 53 1 0 0 0 0 20 2 1 1 0 0 0 20 36 1 0 0 0 0 20 54 1 0 0 0 0 21 24 1 0 0 0 0 22 40 1 1 0 0 0 23 55 1 6 0 0 0 24 41 1 6 0 0 0 25 26 1 0 0 0 0 25 40 1 6 0 0 0 26 42 1 1 0 0 0 27 35 1 0 0 0 0 27 44 1 1 0 0 0 28 17 1 1 0 0 0 28 31 1 0 0 0 0 28 56 1 0 0 0 0 29 45 2 0 0 0 0 29 52 1 0 0 0 0 30 53 1 0 0 0 0 30 55 1 6 0 0 0 31 32 1 0 0 0 0 31 46 1 6 0 0 0 32 33 1 0 0 0 0 32 47 1 1 0 0 0 33 38 1 0 0 0 0 33 48 1 6 0 0 0 34 37 1 0 0 0 0 34 39 1 0 0 0 0 34 49 1 6 0 0 0 35 57 1 1 0 0 0 36 37 1 0 0 0 0 36 58 1 1 0 0 0 37 51 1 1 0 0 0 38 56 1 0 0 0 0 38 58 1 1 0 0 0 39 54 1 0 0 0 0 39 57 1 1 0 0 0 40 3 1 6 0 0 0 41 42 1 6 0 0 0 42 50 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	50994499
ChEMBL	CHEMBL1644522
ZINC

Physicochemical Properties

Molecular Weight:	826.44
ALogP:	-3.642
MLogP:	4.32
XLogP:	1.6
# Rotatable Bonds:	21
Polar Surface Area:	232.52
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	8
# Heavy Atoms:	58

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