NPASS Natural Product

Natural Product: NPC471901

Natural Product ID:	NPC471901
Common Name:	3-O-Acetyl-Lupeolic Acid
IUPAC Name:	(1R,3aR,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-3a,5a,5b,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid
Synonyms:
Molecular Formula:	C32H50O4
Standard InCHIKey:	DULLEXJVWYWBKQ-VDHVTXALSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-19(2)21-11-14-28(4)17-18-30(6)22(26(21)28)9-10-23-29(5)15-13-25(36-20(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h21-26H,1,9-18H2,2-8H3,(H,34,35)/t21-,22+,23+,24+,25-,26+,28+,29+,30+,31+,32+/m0/s1
Canonical SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H]([C@@]1(C)C(=O)O)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)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
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota				PMID[24844534]

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Biological Activity

Activity Type	# Activity
IC50	6
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT136	Cell Line	SK-N-SH	Homo sapiens	IC50	=	4100	nM	21970540
NPT2	Others	Unspecified		IC50	=	4100	nM	21802177
NPT2	Others	Unspecified		IC50	=	4100	nM	8126698
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10000	nM	23149304
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000	nM	18222568
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	51.4	%	10543899
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	10000	nM	8126698

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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 NPC471901 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	135
0.1-0.2	942
0.2-0.3	3482
0.3-0.4	8976
0.4-0.5	7151
0.5-0.6	3747
0.6-0.7	3957
0.7-0.8	2122
0.8-0.85	288
0.85-0.9	67
0.9-0.95	15
0.95-1	7

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Similarity Score	Similarity Level	Natural Product ID
0.8202	Intermediate Similarity	NPC245866
0.8202	Intermediate Similarity	NPC471036
0.8202	Intermediate Similarity	NPC291320
0.8211	Intermediate Similarity	NPC148523
0.8211	Intermediate Similarity	NPC184848

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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 NPC471901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1673
0.2-0.3	3808
0.3-0.4	2344
0.4-0.5	672
0.5-0.6	219
0.6-0.7	203
0.7-0.8	89
0.8-0.85	4
0.85-0.9	0
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.65	Remote Similarity	NPD4689	Approved
0.65	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD5205	Approved
0.65	Remote Similarity	NPD4688	Approved
0.65	Remote Similarity	NPD4138	Approved

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Structure

NPC471901 OpenBabel07101718302D 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 3.1112 1.4666 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 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 -3.5103 1.4634 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 0 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 -0.0000 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 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 1 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 -3.0225 0.6185 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 1 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 -2.5347 1.4634 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 -3.9981 0.6185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -0.2264 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 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 6 30 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 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 24 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 30 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 30 1 6 0 0 0 23 29 1 1 0 0 0 23 31 1 0 0 0 0 24 29 1 1 0 0 0 24 32 1 0 0 0 0 25 32 1 1 0 0 0 25 36 1 0 0 0 0 26 28 1 1 0 0 0 27 32 1 0 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 30 31 1 1 0 0 0 31 7 1 1 0 0 0 32 8 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	90644331
ChEMBL	CHEMBL3289106
ZINC

Physicochemical Properties

Molecular Weight:	498.37
ALogP:	2.7286
MLogP:	4.54
XLogP:	11.202
# Rotatable Bonds:	12
Polar Surface Area:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	36

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