NPASS Natural Product

Natural Product: NPC148414

Natural Product ID:	NPC148414
Common Name:	3-Alpha-Acetoxy-8,24-Diene-Tirucallic Acid
IUPAC Name:	(2S)-2-[(3R,5R,10S,13S,14S,17S)-3-acetyloxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:
Molecular Formula:	C32H50O4
Standard InCHIKey:	FIWGZIBLJWZUEA-JKGVXMGFSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-20(2)10-9-11-22(28(34)35)23-14-18-32(8)25-12-13-26-29(4,5)27(36-21(3)33)16-17-30(26,6)24(25)15-19-31(23,32)7/h10,22-23,26-27H,9,11-19H2,1-8H3,(H,34,35)/t22-,23-,26-,27+,30+,31-,32+/m0/s1
Canonical SMILES:	CC(=CCC[C@@H]([C@@H]1CC[C@]2([C@@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)OC(=O)C)C)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
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota				PMID[24844534]

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Biological Activity

Activity Type	# Activity
IC50	3
Others	3

Activity Type	# Activity
Individual Protein	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10000	nM	23819871
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Activity	=	81.8	%	DrugMatrix in vitro pharmacology data
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Activity	=	63.2	%	23398362
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000	nM	18952420
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	36.8	%	21084196
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	400	nM	18293903

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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 NPC148414 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	125
0.1-0.2	692
0.2-0.3	2889
0.3-0.4	7998
0.4-0.5	8073
0.5-0.6	3751
0.6-0.7	4006
0.7-0.8	2709
0.8-0.85	523
0.85-0.9	93
0.9-0.95	25
0.95-1	5

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Similarity Score	Similarity Level	Natural Product ID
0.8352	Intermediate Similarity	NPC198664
0.8352	Intermediate Similarity	NPC59263
0.8352	Intermediate Similarity	NPC475049
0.8352	Intermediate Similarity	NPC130520
0.8352	Intermediate Similarity	NPC476733

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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 NPC148414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	1123
0.2-0.3	3661
0.3-0.4	2798
0.4-0.5	827
0.5-0.6	257
0.6-0.7	174
0.7-0.8	147
0.8-0.85	36
0.85-0.9	4
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.697	Remote Similarity	NPD4096	Approved
0.6972	Remote Similarity	NPD5250	Approved
0.6972	Remote Similarity	NPD5249	Phase 3
0.6972	Remote Similarity	NPD5248	Approved
0.6972	Remote Similarity	NPD5247	Approved

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Structure

NPC148414 OpenBabel07101718242D 36 39 0 0 1 0 0 0 0 0999 V2000 -4.8126 -4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 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 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 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 -1.5388 -0.5000 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 4.3301 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 -0.9511 0.3090 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 -3.8344 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 7 31 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 20 2 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 32 1 0 0 0 0 19 31 1 0 0 0 0 21 33 2 0 0 0 0 21 36 1 0 0 0 0 22 11 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 31 1 6 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 1 0 0 0 27 29 1 0 0 0 0 27 36 1 6 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 30 6 1 1 0 0 0 31 32 1 6 0 0 0 32 8 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	90644333
ChEMBL	CHEMBL3289097
ZINC

Physicochemical Properties

Molecular Weight:	498.37
ALogP:	3.7287
MLogP:	4.54
XLogP:	8.861
# Rotatable Bonds:	16
Polar Surface Area:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	36

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