NPASS Natural Product

Natural Product: NPC204450

Natural Product ID:	NPC204450
Common Name:	Ganoderenic Acid A
IUPAC Name:	(E)-6-[(5R,7S,10S,13R,14R,15S,17R)-7,15-dihydroxy-4,4,10,13,14-pentamethyl-3,11-dioxo-2,5,6,7,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxohept-5-enoic acid
Synonyms:	Ganoderenic Acid A
Molecular Formula:	C30H42O7
Standard InCHIKey:	OVUOUFPIPZJGME-JQDIJSAQSA-N
Standard InCHI:	InChI=1S/C30H42O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h10,16,18-19,21,23,32,35H,8-9,11-14H2,1-7H3,(H,36,37)/b15-10+/t16?,18-,19+,21+,23+,28+,29-,30+/m1/s1
Canonical SMILES:	O=C(CC(C(=O)O)C)/C=C(/[C@H]1C[C@@H]([C@@]2([C@]1(C)CC(=O)C1=C2[C@@H](O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)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
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota		TM-MC*
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota		TM-MC*
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota		TCMID*
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota		HerDing*
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota		TCMID*

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Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	300000	nM	23092389
NPT168	Cell Line	P388	Mus musculus	IC50	=	7250	nM	23092389
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	7250	nM	23092389
NPT2	Others	Unspecified		IC50	=	445300	nM	24070782
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	119200	nM	22047696
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	=	7250	nM	23092389

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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 NPC204450 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	141
0.1-0.2	754
0.2-0.3	2889
0.3-0.4	6329
0.4-0.5	9255
0.5-0.6	4500
0.6-0.7	4398
0.7-0.8	2218
0.8-0.85	270
0.85-0.9	108
0.9-0.95	23
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.8269	Intermediate Similarity	NPC96268
0.8273	Intermediate Similarity	NPC471854
0.8283	Intermediate Similarity	NPC111015
0.8283	Intermediate Similarity	NPC7165
0.8286	Intermediate Similarity	NPC91034

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 NPC204450 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1290
0.2-0.3	3599
0.3-0.4	2651
0.4-0.5	909
0.5-0.6	209
0.6-0.7	156
0.7-0.8	167
0.8-0.85	37
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
0.7019	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6370	Approved
0.7041	Intermediate Similarity	NPD4195	Approved
0.7059	Intermediate Similarity	NPD4623	Approved
0.7059	Intermediate Similarity	NPD4519	Discontinued

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Structure

CID204450 OpenBabel06191715592D 37 40 0 0 1 0 0 0 0 0999 V2000 1.8204 -2.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2832 -4.9691 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 -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 0.3586 -3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8209 -4.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6891 -0.9746 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 -0.8446 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 -2.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3085 -4.9693 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8462 -4.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4627 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 1.4633 0.0000 C 0 0 1 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 -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 1.6888 0.0005 0.0000 C 0 0 1 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 1.8214 -5.8136 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 2 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 0.3591 -4.9699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0205 1.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5556 -1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0905 1.9620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3957 0.7078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3090 -6.6576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8467 -5.8139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 28 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 29 1 0 0 0 0 15 18 1 0 0 0 0 16 26 1 0 0 0 0 17 31 2 0 0 0 0 18 29 1 6 0 0 0 19 25 1 0 0 0 0 19 32 1 6 0 0 0 20 24 1 0 0 0 0 20 33 2 0 0 0 0 21 27 1 0 0 0 0 21 28 1 6 0 0 0 22 27 1 0 0 0 0 22 34 2 0 0 0 0 23 30 1 1 0 0 0 23 35 1 0 0 0 0 24 25 2 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 36 2 0 0 0 0 26 37 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	14193987
ChEMBL	CHEMBL1922171
ZINC

Physicochemical Properties

Molecular Weight:	514.29
ALogP:	1.2733
MLogP:	3.99
XLogP:	0.491
# Rotatable Bonds:	15
Polar Surface Area:	128.97
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	37

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