NPASS Natural Product

Natural Product: NPC201607

Natural Product ID:	NPC201607
Common Name:	Papyriferic Acid
IUPAC Name:	3-[[(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]oxy]-3-oxopropanoic acid
Synonyms:	Papyriferic Acid
Molecular Formula:	C35H56O8
Standard InCHIKey:	RLVAVWQAAQFUOP-GNYBQDBLSA-N
Standard InCHI:	InChI=1S/C35H56O8/c1-20(36)41-22-18-24-32(6)14-12-25(42-28(39)19-27(37)38)30(2,3)23(32)11-16-33(24,7)34(8)15-10-21(29(22)34)35(9)17-13-26(43-35)31(4,5)40/h21-26,29,40H,10-19H2,1-9H3,(H,37,38)/t21-,22+,23-,24+,25+,26+,29-,32-,33+,34+,35-/m0/s1
Canonical SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@H](C([C@@H]3CC[C@]2([C@]2([C@H]1[C@H](CC2)[C@]1(C)CC[C@@H](O1)C(O)(C)C)C)C)(C)C)OC(=O)CC(=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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	Floral spikes			PMID[17346076]

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Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

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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	=	47600	nM	22275465
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	52200	nM	22275465
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	71700	nM	22275465
NPT91	Cell Line	KB	Homo sapiens	IC50	=	47800	nM	10869191

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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 NPC201607 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 NPC201607 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

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Structure

NPC201607 OpenBabel07101719132D 43 47 0 0 1 0 0 0 0 0999 V2000 2.5996 -3.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8186 -1.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3291 -0.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4152 0.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5428 -0.2681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2955 -2.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2955 1.8576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4213 0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9231 -0.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2702 1.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9915 -0.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9915 -3.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0829 1.5822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1435 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2440 1.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1435 0.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8629 1.3287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4475 -1.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3834 -3.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7516 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8719 0.5545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5996 -1.0799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9915 -1.0799 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2955 -1.0799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8395 -2.5486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6162 0.7610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2314 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5354 -2.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5996 -0.1007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8395 -1.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5940 0.7097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1435 -1.5695 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2955 -0.1007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4475 0.3889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9141 0.3509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9036 -3.0382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0794 -3.0382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2314 -1.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5354 -1.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1273 1.5309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7516 -1.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6875 -3.0382 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 20 1 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 7 33 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 26 1 0 0 0 0 14 32 1 0 0 0 0 15 34 1 0 0 0 0 16 33 1 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 19 28 1 0 0 0 0 20 36 2 0 0 0 0 20 41 1 0 0 0 0 21 10 1 1 0 0 0 21 29 1 0 0 0 0 21 35 1 0 0 0 0 22 29 1 0 0 0 0 22 41 1 1 0 0 0 23 30 1 0 0 0 0 23 32 1 1 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 25 42 1 6 0 0 0 26 31 1 1 0 0 0 26 43 1 0 0 0 0 27 37 2 0 0 0 0 27 38 1 0 0 0 0 28 39 2 0 0 0 0 28 42 1 0 0 0 0 29 34 1 6 0 0 0 31 40 1 0 0 0 0 32 6 1 1 0 0 0 33 34 1 6 0 0 0 34 8 1 6 0 0 0 35 9 1 6 0 0 0 35 43 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	441683
ChEMBL	CHEMBL224050
ZINC

Physicochemical Properties

Molecular Weight:	604.40
ALogP:	1.368
MLogP:	4.43
XLogP:	8.315
# Rotatable Bonds:	19
Polar Surface Area:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	43

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