NPASS Natural Product

Natural Product: NPC54689

Natural Product ID:	NPC54689
Common Name:	16Alpha-Hydroxyeburiconic Acid
IUPAC Name:	(2R)-2-[(5R,10S,13R,14R,16R,17R)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:	16Alpha-Hydroxyeburiconic Acid
Molecular Formula:	C31H48O4
Standard InCHIKey:	MUTPNNQAZRJDSK-WMNQUVFJSA-N
Standard InCHI:	InChI=1S/C31H48O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-24,26,32H,3,9-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,26+,29-,30-,31+/m1/s1
Canonical SMILES:	CC(C(=C)CC[C@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C(=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	Reference
NPO13371	Paepalanthus ramosus	Species	Eriocaulaceae	Eukaryota		UNPD*
NPO18205	Brevibacterium iodinum	Species	Brevibacteriaceae	Bacteria		UNPD*
NPO20036	Mallotus pallidus	Species	Euphorbiaceae	Eukaryota		UNPD*
NPO20795	Melicope melanophloia	Species	Rutaceae	Eukaryota		UNPD*
NPO20918	Pseudotsuga menziesii	Species	Pinaceae	Eukaryota		UNPD*
NPO21268	Heliotropium ramosissimum	Species	Heliotropiaceae	Eukaryota		UNPD*
NPO21659	Daedalea quercina	Species	Coriolaceae	Eukaryota		UNPD*
NPO22868	Pulsatilla dahurica	Species	Ranunculaceae	Eukaryota		UNPD*
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	PMID[19746919]
NPO25850	Urochloa ruziziensis	Species	Poaceae	Eukaryota		UNPD*

Showing 1 to 10 of 10 entries

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Biological Activity

Activity Type	# Activity
IC50	3
Others	5

Activity Type	# Activity
Cell Line	2
Others	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000	nM	19746919
NPT2	Others	Unspecified		IC50	=	348	molar ratio	19746919
NPT2	Others	Unspecified		Inhibition	=	96.4	%	19746919
NPT2	Others	Unspecified		Inhibition	=	70.3	%	19746919
NPT2	Others	Unspecified		Inhibition	=	28.3	%	19746919
NPT2	Others	Unspecified		Inhibition	=	2.2	%	19746919
NPT2	Others	Unspecified		IC50	>	100000	nM	19746919
NPT80	Cell Line	Raji	Homo sapiens	Inhibition	=	70	%	19746919

Showing 1 to 8 of 8 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 NPC54689 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	121
0.1-0.2	747
0.2-0.3	3439
0.3-0.4	10480
0.4-0.5	5597
0.5-0.6	3667
0.6-0.7	4438
0.7-0.8	1999
0.8-0.85	266
0.85-0.9	107
0.9-0.95	21
0.95-1	7

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Similarity Score	Similarity Level	Natural Product ID
0.8315	Intermediate Similarity	NPC145879
0.8315	Intermediate Similarity	NPC472491
0.8315	Intermediate Similarity	NPC475022
0.8315	Intermediate Similarity	NPC31564
0.8315	Intermediate Similarity	NPC51014

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 NPC54689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1330
0.2-0.3	3894
0.3-0.4	2582
0.4-0.5	666
0.5-0.6	191
0.6-0.7	148
0.7-0.8	177
0.8-0.85	34
0.85-0.9	7
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7079	Intermediate Similarity	NPD3702	Approved
0.708	Intermediate Similarity	NPD6319	Approved
0.7113	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6101	Approved
0.7115	Intermediate Similarity	NPD6052	Approved

Showing 1 to 5 of 200 entries

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Structure

CID54689 OpenBabel06191715392D 35 38 0 0 1 0 0 0 0 0999 V2000 2.8619 3.6433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2105 3.9938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4572 1.7364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3803 -2.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2557 -2.4560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5349 0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8057 2.0869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0812 2.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 -1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6897 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2240 -0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3795 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9350 3.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7326 2.3883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 2.4374 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6900 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 0.9746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5355 -1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2243 -1.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5702 3.0894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3800 -1.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5352 -0.4871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9751 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 -2.5554 1.4741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0906 -1.9618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3679 4.0429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4972 2.7879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 20 10 1 6 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 22 2 0 0 0 0 21 29 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 28 1 0 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 25 33 2 0 0 0 0 26 30 1 6 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	12019176
ChEMBL	CHEMBL1077754
ZINC

Physicochemical Properties

Molecular Weight:	484.36
ALogP:	2.4884
MLogP:	4.43
XLogP:	6.084
# Rotatable Bonds:	15
Polar Surface Area:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	35

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