NPASS Natural Product

Natural Product: NPC100917

Natural Product ID:	NPC100917
Common Name:	3-Oxofriedelan-28-Oic Acid
IUPAC Name:	(4aS,6aS,6aR,6bS,8aS,9R,12aS,14aS,14bS)-2,2,6a,6a,8a,9,14a-heptamethyl-10-oxo-3,4,5,6,6b,7,8,9,11,12,12a,13,14,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Molecular Formula:	C30H48O3
Standard InCHIKey:	QZNNDFPVPLYXIF-UDSWSONXSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19-20(31)8-9-21-26(19,4)11-10-22-27(21,5)13-14-29(7)23-18-25(2,3)12-16-30(23,24(32)33)17-15-28(22,29)6/h19,21-23H,8-18H2,1-7H3,(H,32,33)/t19-,21+,22-,23-,26+,27-,28+,29-,30-/m0/s1
Canonical SMILES:	O=C1CC[C@@H]2[C@]([C@H]1C)(C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)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	Collection Location	Collection Time	Reference
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota				PMID[1375626]
NPO30313	Maytenus diversifolia	Species	Celastraceae	Eukaryota				PMID[2095372]

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Biological Activity

Activity Type	# Activity
ED50	4
IC50	1

Activity Type	# Activity
Cell Line	4
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	ED50	=	2.95	ug/ml	17363259
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	ED50	=	15	nM	18973387
NPT759	Cell Line	H9	Homo sapiens	IC50	=	22000	nM	DrugMatrix in vitro pharmacology data
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.18	ug/ml	15921441
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.7	ug/ml	17363259

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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 NPC100917 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	167
0.1-0.2	1897
0.2-0.3	9621
0.3-0.4	8793
0.4-0.5	4855
0.5-0.6	3897
0.6-0.7	1225
0.7-0.8	367
0.8-0.85	47
0.85-0.9	12
0.9-0.95	5
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.7349	Intermediate Similarity	NPC88716
0.7349	Intermediate Similarity	NPC242468
0.7349	Intermediate Similarity	NPC98442
0.7349	Intermediate Similarity	NPC51700
0.7349	Intermediate Similarity	NPC142415

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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 NPC100917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	3100
0.2-0.3	3846
0.3-0.4	1247
0.4-0.5	393
0.5-0.6	213
0.6-0.7	65
0.7-0.8	26
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5607	Remote Similarity	NPD8133	Approved
0.561	Remote Similarity	NPD4747	Approved
0.561	Remote Similarity	NPD4691	Approved
0.5618	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6001	Approved

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Structure

NPC100917 OpenBabel07101718332D 33 37 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 0.0000 -1.0000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 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 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 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 3.4641 -1.0000 0.0000 C 0 0 1 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 0.8660 0.5000 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 1 0 0 0 20 31 2 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 23 29 1 6 0 0 0 23 30 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 6 0 0 0 30 24 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	44593504
ChEMBL	CHEMBL517324
ZINC

Physicochemical Properties

Molecular Weight:	456.36
ALogP:	2.3357
MLogP:	4.43
XLogP:	10.119
# Rotatable Bonds:	9
Polar Surface Area:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	33

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