NPASS Natural Product

Natural Product: NPC261616

Natural Product ID:	NPC261616
Common Name:	(20S)-3Alpha-Acetoxylupan-29-Oic Acid
IUPAC Name:	(2S)-2-[(1R,3aR,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-acetyloxy-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]propanoic acid
Synonyms:
Molecular Formula:	C32H52O4
Standard InCHIKey:	XNJAMPWVGPBWJX-CEJIPEKBSA-N
Standard InCHI:	InChI=1S/C32H52O4/c1-19(27(34)35)21-11-14-29(5)17-18-31(7)22(26(21)29)9-10-24-30(6)15-13-25(36-20(2)33)28(3,4)23(30)12-16-32(24,31)8/h19,21-26H,9-18H2,1-8H3,(H,34,35)/t19-,21-,22+,23-,24+,25+,26+,29+,30-,31+,32+/m0/s1
Canonical SMILES:	CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)[C@@H](C(=O)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
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant			PMID[24467317]

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Biological Activity

Activity Type	# Activity
IC50	6
Others	1

Activity Type	# Activity
Cell Line	2
Others	5

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000	nM	23822611
NPT2	Others	Unspecified		IC50	>	10000	nM	20553004
NPT2	Others	Unspecified		IC50	>	10000	nM	18077363
NPT2	Others	Unspecified		IC50	=	7480	nM	12852754
NPT2	Others	Unspecified		Activity	=	98.5	%	24359277
NPT2	Others	Unspecified		IC50	>	10000	nM	PubChem BioAssay data set
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	PubChem BioAssay data set

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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 NPC261616 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	201
0.1-0.2	1672
0.2-0.3	5549
0.3-0.4	11298
0.4-0.5	4204
0.5-0.6	3758
0.6-0.7	3101
0.7-0.8	942
0.8-0.85	100
0.85-0.9	50
0.9-0.95	14
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7912	Intermediate Similarity	NPC327788
0.7922	Intermediate Similarity	NPC474962
0.7927	Intermediate Similarity	NPC305835
0.7931	Intermediate Similarity	NPC473319
0.7931	Intermediate Similarity	NPC3032

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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 NPC261616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	2742
0.2-0.3	3779
0.3-0.4	1572
0.4-0.5	366
0.5-0.6	247
0.6-0.7	154
0.7-0.8	20
0.8-0.85	11
0.85-0.9	7
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.596	Remote Similarity	NPD6700	Approved
0.5966	Remote Similarity	NPD8293	Discontinued
0.5981	Remote Similarity	NPD4767	Approved
0.5981	Remote Similarity	NPD4768	Approved
0.5983	Remote Similarity	NPD8328	Phase 3

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Structure

NPC261616 OpenBabel07101719512D 36 40 0 0 1 0 0 0 0 0999 V2000 -4.7183 -0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -4.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 -0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1379 2.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0360 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4626 1.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7640 -0.7415 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3796 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4626 0.1863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1112 -1.4666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2245 -4.3902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4127 -2.3944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1569 -1.2637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 7 31 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 32 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 31 1 0 0 0 0 19 1 1 1 0 0 0 19 27 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 19 1 6 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 22 31 1 6 0 0 0 23 28 1 0 0 0 0 23 30 1 1 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 36 1 6 0 0 0 26 29 1 1 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 29 5 1 1 0 0 0 30 6 1 1 0 0 0 31 32 1 1 0 0 0 32 8 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	76313950
ChEMBL	CHEMBL3109384
ZINC

Physicochemical Properties

Molecular Weight:	500.39
ALogP:	2.2397
MLogP:	4.54
XLogP:	11.368
# Rotatable Bonds:	13
Polar Surface Area:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	36

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