NPASS Natural Product

Natural Product: NPC192744

Natural Product ID:	NPC192744
Common Name:	Betunolic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:	Betunolic Acid
Molecular Formula:	C30H46O3
Standard InCHIKey:	SLJTWDNVZKIDAU-SVAFSPIFSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-22,24H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,24+,27-,28+,29+,30-/m0/s1
Canonical SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C(=O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota	UNPD*
NPO11134	Himalaiella deltoidea	Species	Asteraceae	Eukaryota	UNPD*
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	UNPD*
NPO11436	Baeomyces roseus	Species	Baeomycetaceae	Eukaryota	UNPD*
NPO11808	Ania latifolia	Species	Orchidaceae	Eukaryota	UNPD*
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	UNPD*
NPO11987	Silene inflata	Species	Caryophyllaceae	Eukaryota	UNPD*
NPO11994	Thesium humile	Species	Thesiaceae	Eukaryota	UNPD*
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	UNPD*
NPO12255	Jasminum humile	Species	Oleaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
EC50	14
ED50	13
IC50	65
Others	18
Potency	14

Activity Type	# Activity
Cell Line	66
Individual Protein	10
Organism	20
Others	28

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		4109.5	nM	PubChem BioAssay data set
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	14.47	ug/ml	21106454
NPT111	Cell Line	K562	Homo sapiens	IC50	=	16100	nM	17346076
NPT111	Cell Line	K562	Homo sapiens	IC50	=	6000	nM	17371067
NPT111	Cell Line	K562	Homo sapiens	IC50	=	17000	nM	15270560
NPT111	Cell Line	K562	Homo sapiens	IC50	=	6000	nM	15270560
NPT112	Cell Line	MOLT-4	Homo sapiens	ED50	=	1.2	ug/ml	15225732
NPT1174	Cell Line	A375	Homo sapiens	IC50	=	28900	nM	25874331
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	Inhibition	=	50	%	25240731
NPT1215	Cell Line	8505C	Homo sapiens	IC50	=	14000	nM	23973824

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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 NPC192744 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	94
0.1-0.2	962
0.2-0.3	4584
0.3-0.4	11785
0.4-0.5	4571
0.5-0.6	4481
0.6-0.7	2935
0.7-0.8	1289
0.8-0.85	120
0.85-0.9	52
0.9-0.95	15
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.7975	Intermediate Similarity	NPC201027
0.7975	Intermediate Similarity	NPC192540
0.7975	Intermediate Similarity	NPC279666
0.7976	Intermediate Similarity	NPC221758
0.7976	Intermediate Similarity	NPC85774

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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 NPC192744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	122
0.1-0.2	1706
0.2-0.3	4118
0.3-0.4	2145
0.4-0.5	570
0.5-0.6	230
0.6-0.7	165
0.7-0.8	99
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6306	Remote Similarity	NPD6335	Approved
0.631	Remote Similarity	NPD6923	Approved
0.631	Remote Similarity	NPD6922	Approved
0.6333	Remote Similarity	NPD5368	Approved
0.6346	Remote Similarity	NPD6008	Approved

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Structure

CID192744 OpenBabel06191715582D 33 37 0 0 1 0 0 0 0 0999 V2000 5.7215 0.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1861 0.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4517 1.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9589 0.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0243 1.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8712 -1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6452 0.9505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8223 1.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1130 -1.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6443 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 2.8485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8231 2.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 -0.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2915 -1.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8231 -1.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6460 -1.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7838 0.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1127 -0.4738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6455 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6446 0.9495 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4677 2.3733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4684 -0.4743 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4689 -2.3731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4672 1.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8226 1.4247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8229 -0.4748 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 2.4686 -1.4237 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3206 2.8651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5660 -2.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1746 -3.0082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 19 18 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 31 2 0 0 0 0 24 30 1 1 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 25 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	122844
ChEMBL	CHEMBL431525
ZINC

Physicochemical Properties

Molecular Weight:	454.34
ALogP:	2.9192
MLogP:	4.43
XLogP:	8.8
# Rotatable Bonds:	9
Polar Surface Area:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	33

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