NPASS Natural Product

Natural Product: NPC26413

Natural Product ID:	NPC26413
Common Name:	Acetyl-11-Keto-Beta-Boswellic Acid
IUPAC Name:	(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-acetyloxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
Synonyms:
Molecular Formula:	C32H48O5
Standard InCHIKey:	HMMGKOVEOFBCAU-BCDBGHSCSA-N
Standard InCHI:	InChI=1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23-,24-,25+,26-,28-,29+,30-,31-,32-/m1/s1
Canonical SMILES:	CC(=O)O[C@@H]1CC[C@]2([C@H]([C@@]1(C)C(=O)O)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C)[C@H](C)CC1)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
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota				PMID[15730241]
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota				PMID[24844534]

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Biological Activity

Activity Type	# Activity
IC50	12
Others	22

Activity Type	# Activity
Cell Line	19
Individual Protein	6
Organism	2
Others	5
Tissue	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	15600	nM	16933872
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	81.15	%	26105195
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	=	63	%	10.6019/CHEMBL1201861
NPT1138	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Homo sapiens	Inhibition	=	52	%	22738638
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11000	nM	24460410
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	59	%	Open TG-GATES in vivo data: Biochemistry
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	19400	nM	23398362
NPT139	Cell Line	HT-29	Homo sapiens	Inhibition	=	24	%	7623030
NPT139	Cell Line	HT-29	Homo sapiens	GI	=	88	%	10924166
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	40	%	23398362

Showing 1 to 10 of 34 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 NPC26413 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	147
0.1-0.2	782
0.2-0.3	2758
0.3-0.4	5773
0.4-0.5	9702
0.5-0.6	4739
0.6-0.7	3836
0.7-0.8	2658
0.8-0.85	287
0.85-0.9	146
0.9-0.95	53
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.8526	High Similarity	NPC158059
0.8526	High Similarity	NPC473690
0.8526	High Similarity	NPC287118
0.8526	High Similarity	NPC275809
0.8556	High Similarity	NPC200752

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 NPC26413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1267
0.2-0.3	3451
0.3-0.4	2723
0.4-0.5	958
0.5-0.6	301
0.6-0.7	172
0.7-0.8	127
0.8-0.85	3
0.85-0.9	0
0.9-0.95	4
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD8377	Approved

Showing 1 to 5 of 200 entries

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Structure

NPC26413 OpenBabel07101718252D 37 41 0 0 1 0 0 0 0 0999 V2000 -5.0724 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5124 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3816 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3816 -3.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5362 -2.4405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0243 -0.6189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 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 2.5362 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2270 -4.3929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0005 -0.6189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.2265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -2.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 20 1 0 0 0 0 6 30 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 31 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 2 1 1 0 0 0 19 25 1 0 0 0 0 20 33 2 0 0 0 0 20 37 1 0 0 0 0 21 25 1 0 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 34 2 0 0 0 0 23 29 1 1 0 0 0 23 32 1 0 0 0 0 24 32 1 6 0 0 0 24 37 1 0 0 0 0 25 28 1 6 0 0 0 26 29 1 1 0 0 0 26 31 1 0 0 0 0 27 32 1 0 0 0 0 27 35 2 0 0 0 0 27 36 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	11168203
ChEMBL	CHEMBL237111
ZINC

Physicochemical Properties

Molecular Weight:	512.35
ALogP:	1.4162
MLogP:	4.43
XLogP:	8.442
# Rotatable Bonds:	12
Polar Surface Area:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	37

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