NPASS Natural Product

Natural Product: NPC117445

Natural Product ID:	NPC117445
Common Name:	Lanatoside C
IUPAC Name:	[(2R,3R,4S,6S)-6-[(2R,3S,4S,6S)-6-[(2R,3S,4S,6R)-6-[[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-2-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl] acetate
Synonyms:	Cedilanid; Lanatoside C
Molecular Formula:	C49H76O20
Standard InCHIKey:	JAYAGJDXJIDEKI-PTGWOZRBSA-N
Standard InCHI:	InChI=1S/C49H76O20/c1-21-43(67-38-17-32(53)44(22(2)62-38)68-39-18-33(64-24(4)51)45(23(3)63-39)69-46-42(58)41(57)40(56)34(19-50)66-46)31(52)16-37(61-21)65-27-9-11-47(5)26(14-27)7-8-29-30(47)15-35(54)48(6)28(10-12-49(29,48)59)25-13-36(55)60-20-25/h13,21-23,26-35,37-46,50,52-54,56-59H,7-12,14-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29-,30+,31+,32+,33+,34-,35-,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48+,49+/m1/s1
Canonical SMILES:	OC[C@H]1O[C@@H](O[C@@H]2[C@@H](C)O[C@H](C[C@@H]2OC(=O)C)O[C@H]2[C@@H](O)C[C@@H](O[C@@H]2C)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]3C[C@@H](O)[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)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
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	UNPD*
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	UNPD*
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	UNPD*
NPO17635	Aria arguta	Species	Rosaceae	Eukaryota	UNPD*
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	UNPD*
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	UNPD*
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	UNPD*
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	UNPD*
NPO19093	Streptomyces aburaviensis	Species	Streptomycetaceae	Bacteria	UNPD*
NPO19175	Iguana iguana	Species	Iguanidae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
AC50	1
GI50	58
IC50	1
Others	7
Potency	60

Activity Type	# Activity
Cell Line	64
Individual Protein	19
Others	44

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		183.6	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		1835.6	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		39.99	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		18.03	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		33.19	nM	PubChem BioAssay data set
NPT1283	Individual Protein	Paired box protein Pax-8	Homo sapiens	AC50	=	801	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	Survival	=	40	%	19894733
NPT139	Cell Line	HT-29	Homo sapiens	GI50		47.97	nM	PubChem BioAssay data set
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50		59.7	nM	PubChem BioAssay data set
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50		165.2	nM	PubChem BioAssay data set

Showing 1 to 10 of 118 entries

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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 NPC117445 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	184
0.1-0.2	1156
0.2-0.3	3264
0.3-0.4	6097
0.4-0.5	9076
0.5-0.6	5562
0.6-0.7	3276
0.7-0.8	1644
0.8-0.85	401
0.85-0.9	145
0.9-0.95	60
0.95-1	24

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Similarity Score	Similarity Level	Natural Product ID
0.8584	High Similarity	NPC208594
0.8584	High Similarity	NPC152584
0.8584	High Similarity	NPC69737
0.8584	High Similarity	NPC473199
0.8596	High Similarity	NPC51172

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 NPC117445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1543
0.2-0.3	4006
0.3-0.4	2324
0.4-0.5	614
0.5-0.6	314
0.6-0.7	131
0.7-0.8	26
0.8-0.85	1
0.85-0.9	3
0.9-0.95	4
0.95-1	7

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.584	Remote Similarity	NPD7087	Discontinued
0.584	Remote Similarity	NPD5281	Approved
0.5847	Remote Similarity	NPD7514	Phase 3
0.585	Remote Similarity	NPD7260	Phase 2
0.5854	Remote Similarity	NPD6672	Approved

Showing 1 to 5 of 200 entries

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Structure

CID117445 OpenBabel06191715472D 69 77 0 0 1 0 0 0 0 0999 V2000 -6.0622 -2.5000 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 -2.5000 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 -11.2583 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5782 -7.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3268 -10.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3323 -9.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4548 -9.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 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 -2.5981 0.5000 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 -15.1184 -8.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7117 -8.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 -6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.7335 -9.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.2583 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.2583 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 1 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 -12.9904 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -16.3208 -9.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -7.7942 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -10.3923 -7.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.9904 -8.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.1244 -9.0000 0.0000 C 0 0 2 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 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.2344 -9.5371 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7660 -8.0664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.1129 -8.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 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 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 24 1 0 0 0 0 6 48 1 0 0 0 0 7 8 1 0 0 0 0 7 26 1 0 0 0 0 8 29 1 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 12 1 0 0 0 0 10 28 1 0 0 0 0 11 47 1 0 0 0 0 12 49 1 0 0 0 0 13 25 2 0 0 0 0 13 36 1 0 0 0 0 14 26 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 0 0 0 0 15 35 1 0 0 0 0 16 31 1 0 0 0 0 16 37 1 0 0 0 0 17 32 1 0 0 0 0 17 38 1 0 0 0 0 18 33 1 0 0 0 0 18 39 1 0 0 0 0 19 50 1 0 0 0 0 20 25 1 0 0 0 0 20 60 1 0 0 0 0 21 1 1 1 0 0 0 21 43 1 0 0 0 0 21 61 1 0 0 0 0 22 2 1 1 0 0 0 22 44 1 0 0 0 0 22 62 1 0 0 0 0 23 3 1 1 0 0 0 23 45 1 0 0 0 0 23 63 1 0 0 0 0 24 51 2 0 0 0 0 24 64 1 0 0 0 0 25 28 1 0 0 0 0 26 47 1 1 0 0 0 27 65 1 6 0 0 0 28 48 1 6 0 0 0 29 30 1 0 0 0 0 29 49 1 1 0 0 0 30 47 1 6 0 0 0 31 43 1 0 0 0 0 31 52 1 6 0 0 0 32 44 1 0 0 0 0 32 53 1 6 0 0 0 33 45 1 0 0 0 0 33 64 1 6 0 0 0 34 19 1 6 0 0 0 34 40 1 0 0 0 0 34 66 1 0 0 0 0 35 48 1 6 0 0 0 35 54 1 0 0 0 0 36 55 2 0 0 0 0 36 60 1 0 0 0 0 37 61 1 0 0 0 0 37 65 1 1 0 0 0 38 62 1 0 0 0 0 38 67 1 1 0 0 0 39 63 1 0 0 0 0 39 68 1 1 0 0 0 40 41 1 0 0 0 0 40 56 1 1 0 0 0 41 42 1 0 0 0 0 41 57 1 6 0 0 0 42 46 1 0 0 0 0 42 58 1 1 0 0 0 43 67 1 6 0 0 0 44 68 1 6 0 0 0 45 69 1 6 0 0 0 46 66 1 0 0 0 0 46 69 1 6 0 0 0 47 5 1 6 0 0 0 48 49 1 6 0 0 0 49 59 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	656630
ChEMBL	CHEMBL506569
ZINC

Physicochemical Properties

Molecular Weight:	984.49
ALogP:	-5.046
MLogP:	4.65
XLogP:	1.377
# Rotatable Bonds:	26
Polar Surface Area:	288.28
# H-Bond Aceptor:	20
# H-Bond Donor:	8
# Rings:	9
# Heavy Atoms:	69

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