NPASS Natural Product

Natural Product: NPC233836

Natural Product ID:	NPC233836
Common Name:	3-Alpha-Hydroxy-8,24-Diene-Tirucallic Acid
IUPAC Name:	(2S)-2-[(3R,5R,10S,13S,14S,17S)-3-hydroxy-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:	C30H48O3
Standard InCHIKey:	NBSBUIQBEPROBM-IMJUUJEHSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24-25,31H,8,10-18H2,1-7H3,(H,32,33)/t20-,21-,24-,25+,28+,29-,30+/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)O)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
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota				TM-MC*
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota				PMID[24844534]

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Biological Activity

Activity Type	# Activity
IC50	3
Others	2

Activity Type	# Activity
Individual Protein	5

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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	24844534
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Activity	=	81.9	%	24844534
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000	nM	24844534
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	3.5	%	24844534
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	1100	nM	24844534

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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 NPC233836 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	114
0.1-0.2	676
0.2-0.3	3095
0.3-0.4	9463
0.4-0.5	6791
0.5-0.6	3771
0.6-0.7	3895
0.7-0.8	2285
0.8-0.85	544
0.85-0.9	210
0.9-0.95	33
0.95-1	12

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Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC255809
0.8571	High Similarity	NPC173875
0.8587	High Similarity	NPC43747
0.8588	High Similarity	NPC278648
0.8588	High Similarity	NPC476082

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 NPC233836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	1163
0.2-0.3	3815
0.3-0.4	2678
0.4-0.5	780
0.5-0.6	237
0.6-0.7	150
0.7-0.8	168
0.8-0.85	33
0.85-0.9	7
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7048	Intermediate Similarity	NPD6412	Phase 2
0.7053	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6319	Approved
0.7059	Intermediate Similarity	NPD6922	Approved
0.7059	Intermediate Similarity	NPD6923	Approved

Showing 1 to 5 of 200 entries

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Structure

CID233836 OpenBabel06191716032D 33 36 0 0 1 0 0 0 0 0999 V2000 0.0789 6.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4621 5.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2526 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6692 4.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0970 4.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2728 3.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6885 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2210 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4934 5.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 2.4357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8448 1.4617 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2212 -1.4613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8138 2.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9744 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 5.0874 -1.9610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2102 3.4269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3861 1.7490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 20 10 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 1 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 31 1 1 0 0 0 26 32 2 0 0 0 0 26 33 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	441677
ChEMBL	CHEMBL3289096
ZINC

Physicochemical Properties

Molecular Weight:	456.36
ALogP:	3.3496
MLogP:	4.43
XLogP:	8.121
# Rotatable Bonds:	14
Polar Surface Area:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	33

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