NPASS Natural Product

Natural Product: NPC56777

Natural Product ID:	NPC56777
Common Name:	Methyl Papyriferate
IUPAC Name:	3-O-[(3R,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 1-O-methyl propanedioate
Synonyms:	Methyl Papyriferate
Molecular Formula:	C36H58O8
Standard InCHIKey:	ZTNOAHJHQOCVJC-ZSIJTDDESA-N
Standard InCHI:	InChI=1S/C36H58O8/c1-21(37)42-23-19-25-33(6)15-13-26(43-29(39)20-28(38)41-10)31(2,3)24(33)12-17-34(25,7)35(8)16-11-22(30(23)35)36(9)18-14-27(44-36)32(4,5)40/h22-27,30,40H,11-20H2,1-10H3/t22-,23+,24-,25+,26+,27+,30-,33-,34+,35+,36-/m0/s1
Canonical SMILES:	COC(=O)CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2C[C@@H](OC(=O)C)[C@H]2[C@@]1(C)CC[C@@H]2[C@]1(C)CC[C@@H](O1)C(O)(C)C)C)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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	Floral spikes			PMID[17346076]

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Biological Activity

Activity Type	# Activity
IC50	6
Others	2

Activity Type	# Activity
Cell Line	5
Others	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	32600	nM	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified		IC50	=	32100	nM	4020828
NPT2	Others	Unspecified		FC	=	1.5		25822739
NPT2	Others	Unspecified		FC	=	51.6		18077363
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	49600	nM	DrugMatrix in vitro pharmacology data
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	48900	nM	DrugMatrix in vitro pharmacology data
NPT91	Cell Line	KB	Homo sapiens	IC50	=	26700	nM	19715320
NPT91	Cell Line	KB	Homo sapiens	IC50	=	33800	nM	DrugMatrix in vitro pharmacology data

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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 NPC56777 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	228
0.1-0.2	1923
0.2-0.3	5038
0.3-0.4	11410
0.4-0.5	4525
0.5-0.6	3725
0.6-0.7	3234
0.7-0.8	730
0.8-0.85	58
0.85-0.9	7
0.9-0.95	8
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.7634	Intermediate Similarity	NPC476435
0.7634	Intermediate Similarity	NPC476379
0.7634	Intermediate Similarity	NPC281004
0.764	Intermediate Similarity	NPC211049
0.764	Intermediate Similarity	NPC12933

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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 NPC56777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	3027
0.2-0.3	3771
0.3-0.4	1321
0.4-0.5	383
0.5-0.6	266
0.6-0.7	101
0.7-0.8	13
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
0.56	Remote Similarity	NPD6067	Discontinued
0.5604	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6079	Approved
0.5619	Remote Similarity	NPD6903	Approved
0.5619	Remote Similarity	NPD6672	Approved

Showing 1 to 5 of 179 entries

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Structure

NPC56777 OpenBabel07101718192D 44 48 0 0 1 0 0 0 0 0999 V2000 2.6007 -3.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8220 -1.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3322 -0.7218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4163 0.1765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5435 -0.2682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2974 -2.0599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2974 1.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4233 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9235 -0.6285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0842 -1.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2711 1.4496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9941 -0.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9941 -3.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0830 1.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1457 -2.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2454 1.3472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1457 0.3890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8633 1.3293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4490 -1.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3875 -3.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7523 -2.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8727 0.5547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6007 -1.0803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9941 -1.0803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2974 -1.0803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8424 -2.5497 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6165 0.7613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2359 -2.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5392 -2.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6007 -0.1008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8424 -1.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5947 0.7100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1457 -1.5701 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2974 -0.1008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4490 0.3890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9145 0.3511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9040 -3.0395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0842 -3.0395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5392 -1.5701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1283 1.5316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2359 -1.5701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7523 -1.5701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6908 -3.0395 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 21 1 0 0 0 0 2 31 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 7 34 1 0 0 0 0 10 41 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 18 1 0 0 0 0 14 27 1 0 0 0 0 15 33 1 0 0 0 0 16 35 1 0 0 0 0 17 34 1 0 0 0 0 18 36 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 28 1 0 0 0 0 20 29 1 0 0 0 0 21 37 2 0 0 0 0 21 42 1 0 0 0 0 22 11 1 1 0 0 0 22 30 1 0 0 0 0 22 36 1 0 0 0 0 23 30 1 0 0 0 0 23 42 1 1 0 0 0 24 31 1 0 0 0 0 24 33 1 1 0 0 0 25 33 1 1 0 0 0 25 34 1 0 0 0 0 26 31 1 0 0 0 0 26 43 1 6 0 0 0 27 32 1 1 0 0 0 27 44 1 0 0 0 0 28 38 2 0 0 0 0 28 41 1 0 0 0 0 29 39 2 0 0 0 0 29 43 1 0 0 0 0 30 35 1 6 0 0 0 32 40 1 0 0 0 0 33 6 1 1 0 0 0 34 35 1 6 0 0 0 35 8 1 6 0 0 0 36 9 1 6 0 0 0 36 44 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44421653
ChEMBL	CHEMBL225369
ZINC

Physicochemical Properties

Molecular Weight:	618.41
ALogP:	1.619
MLogP:	4.54
XLogP:	8.636
# Rotatable Bonds:	20
Polar Surface Area:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	44

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