NPASS Natural Product

Natural Product: NPC148523

Natural Product ID:	NPC148523
Common Name:	11-Keto Boswellic Acid
IUPAC Name:	(3R,4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-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:	11-Keto Boswellic Acid
Molecular Formula:	C30H46O4
Standard InCHIKey:	YIMHGPSYDOGBPI-YZCVQEKWSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21-,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1
Canonical SMILES:	C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC(=O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@H]([C@]1(C)C(=O)O)O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Show entries

Search:

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota	PMID[15730241]
NPO10639	Olibanun	NA	NA	NA	TCMSP*
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	TM-MC*
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	TCM_Taiwan*
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota	PMID[24844534]

Showing 1 to 5 of 5 entries

Previous1Next

Biological Activity

Activity Type	# Activity
IC50	14
LD50	1
Others	22

Activity Type	# Activity
Cell Line	17
Individual Protein	10
Organism	2
Others	6
Tissue	2

Show entries

Search:

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	=	52	%	20100662
NPT1138	Individual Protein	11-beta-hydroxysteroid dehydrogenase 2	Homo sapiens	Inhibition	=	68	%	20100662
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	32000	nM	21334793
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	35	%	22123322
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	IC50	=	9450	nM	18707891
NPT139	Cell Line	HT-29	Homo sapiens	Inhibition	=	7	%	17950603
NPT139	Cell Line	HT-29	Homo sapiens	GI	=	39	%	22123322
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	71900	nM	25618017
NPT1591	Individual Protein	Prolyl endopeptidase	Homo sapiens	IC50	=	36320	nM	15730241
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	50000	nM	21334793

Showing 1 to 10 of 36 entries

Previous1 2 3 4Next

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 NPC148523 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	750
0.2-0.3	2835
0.3-0.4	6285
0.4-0.5	9441
0.5-0.6	4751
0.6-0.7	3570
0.7-0.8	2594
0.8-0.85	271
0.85-0.9	110
0.9-0.95	121
0.95-1	20

Show entries

Search:

Similarity Score	Similarity Level	Natural Product ID
0.871	High Similarity	NPC474806
0.871	High Similarity	NPC474436
0.871	High Similarity	NPC63118
0.871	High Similarity	NPC133579
0.8723	High Similarity	NPC473240

Showing 1 to 5 of 200 entries

Previous1 2 3 4 5…40Next

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC148523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1286
0.2-0.3	3496
0.3-0.4	2741
0.4-0.5	925
0.5-0.6	234
0.6-0.7	175
0.7-0.8	142
0.8-0.85	6
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Show entries

Search:

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6739	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7604	Phase 2
0.6777	Remote Similarity	NPD7507	Approved
0.6796	Remote Similarity	NPD6050	Approved

Showing 1 to 5 of 200 entries

Previous1 2 3 4 5…40Next

Structure

CID148523 OpenBabel06191715522D 34 38 0 0 1 0 0 0 0 0999 V2000 2.5315 4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0186 -2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 3.4103 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 2.9231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3753 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0443 -2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 0.4872 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 -2.5315 -1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -3.1492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0699 -2.3054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 28 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 2 1 1 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 20 31 2 0 0 0 0 21 27 1 1 0 0 0 21 30 1 0 0 0 0 22 30 1 6 0 0 0 22 32 1 0 0 0 0 23 26 1 6 0 0 0 24 27 1 1 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	9847548
ChEMBL	CHEMBL437964
ZINC

Physicochemical Properties

Molecular Weight:	470.34
ALogP:	1.0371
MLogP:	4.32
XLogP:	8.131
# Rotatable Bonds:	10
Polar Surface Area:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	34

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs