NPASS Natural Product

Natural Product: NPC201459

Natural Product ID:	NPC201459
Common Name:	Betulone
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms:	Betulone
Molecular Formula:	C30H48O2
Standard InCHIKey:	JYDNKGUBLIKNAM-CNRMHUMKSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-23,25,31H,1,8-18H2,2-7H3/t20-,21+,22-,23+,25+,27-,28+,29+,30+/m0/s1
Canonical SMILES:	OC[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CCC(=O)C3(C)C)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	Reference
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota			UNPD*
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota			UNPD*
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota			UNPD*
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota			UNPD*
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota			UNPD*
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota			UNPD*
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota			UNPD*
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota			UNPD*
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota			UNPD*
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	PMID[16038541]

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Biological Activity

Activity Type	# Activity
ED50	1
IC50	14
Others	3

Activity Type	# Activity
Cell Line	9
Organism	4
Others	5

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	10	ug/ml	16038541
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10	ug/ml	16038541
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000	nM	24467317
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	10	ug/ml	16038541
NPT2	Others	Unspecified		IC50	>	10000	nM	24467317
NPT2	Others	Unspecified		Ratio CC50/IC50	>	24.5		25927586
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50	%	25927586
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	4100	nM	25927586
NPT319	Cell Line	B16	Mus musculus	ED50	=	0.19	nM	12027734
NPT319	Cell Line	B16	Mus musculus	IC50	=	29300	nM	12027734

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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 NPC201459 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	93
0.1-0.2	896
0.2-0.3	4305
0.3-0.4	11927
0.4-0.5	4680
0.5-0.6	4320
0.6-0.7	2862
0.7-0.8	1516
0.8-0.85	227
0.85-0.9	42
0.9-0.95	19
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.814	Intermediate Similarity	NPC474245
0.814	Intermediate Similarity	NPC26959
0.814	Intermediate Similarity	NPC477943
0.814	Intermediate Similarity	NPC2983
0.814	Intermediate Similarity	NPC24772

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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 NPC201459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	1615
0.2-0.3	4176
0.3-0.4	2239
0.4-0.5	535
0.5-0.6	185
0.6-0.7	174
0.7-0.8	97
0.8-0.85	17
0.85-0.9	2
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6559	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5250	Approved
0.6571	Remote Similarity	NPD5169	Approved
0.6571	Remote Similarity	NPD5248	Approved

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Structure

CID201459 OpenBabel06191715592D 32 36 0 0 1 0 0 0 0 0999 V2000 5.7135 0.3460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1803 0.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4468 1.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9548 0.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0243 1.9117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8700 -1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6429 0.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8212 1.4232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1072 -1.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6420 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6434 2.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 2.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8209 -0.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2869 -1.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 -1.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6437 -1.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 -2.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7771 0.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1069 -0.4732 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6432 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6423 0.9482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9486 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4643 2.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4649 -0.4736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4637 1.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8214 1.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8217 -0.4741 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 2.4652 -1.4217 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1702 -3.0039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3159 2.8610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 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 21 1 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 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 18 31 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 30 1 1 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 18 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	10411004
ChEMBL	CHEMBL469284
ZINC

Physicochemical Properties

Molecular Weight:	440.37
ALogP:	2.7103
MLogP:	4.54
XLogP:	9.107
# Rotatable Bonds:	9
Polar Surface Area:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	32

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