NPASS Natural Product

Natural Product: NPC178383

Natural Product ID:	NPC178383
Common Name:	Betulin
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms:	Betulin
Molecular Formula:	C30H50O2
Standard InCHIKey:	FVWJYYTZTCVBKE-ROUWMTJPSA-N
Standard InCHI:	InChI=1S/C30H50O2/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/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,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)CC[C@@H](C3(C)C)O)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	Collection Time	Reference
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves	Niigata City, Niigata Province, Japan	2000-NOV	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota				UNPD*
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota				TM-MC*
NPO10354	Urbanodendron verrucosum	Species	Lauraceae	Eukaryota				UNPD*
NPO10362	Peniophora affinis	Species	Peniophoraceae	Eukaryota				UNPD*
NPO10560	Adenia fruticosa	Species	Passifloraceae	Eukaryota				UNPD*
NPO1071	Parerythropodium fulvum	NA	NA	NA				UNPD*
NPO10719	Centrosema haitense	Species	Fabaceae	Eukaryota				UNPD*
NPO10730	Alpinia calcarata	Species	Zingiberaceae	Eukaryota				UNPD*
NPO11002	Hopea jucunda	Species	Dipterocarpaceae	Eukaryota				UNPD*

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Biological Activity

Activity Type	# Activity
EC50	24
ED50	7
GI50	58
IC50	66
Others	37

Activity Type	# Activity
Cell Line	128
Individual Protein	15
Organism	13
Others	36

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5	ug/ml	15270571
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	38600	nM	11754608
NPT111	Cell Line	K562	Homo sapiens	IC50	>	250000	nM	16051489
NPT111	Cell Line	K562	Homo sapiens	GI50		15848.93	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		32359.37	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		33962.53	nM	PubChem BioAssay data set
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	10	ug/ml	16038541
NPT1174	Cell Line	A375	Homo sapiens	IC50	=	28000	nM	26280921
NPT1215	Cell Line	8505C	Homo sapiens	EC50	>	30000	nM	26007303
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	250000	nM	16051489

Showing 1 to 10 of 181 entries

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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 NPC178383 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	90
0.1-0.2	1183
0.2-0.3	5045
0.3-0.4	12361
0.4-0.5	4493
0.5-0.6	3447
0.6-0.7	2863
0.7-0.8	1032
0.8-0.85	214
0.85-0.9	105
0.9-0.95	37
0.95-1	19

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Similarity Score	Similarity Level	Natural Product ID
0.84	Intermediate Similarity	NPC285893
0.84	Intermediate Similarity	NPC28657
0.84	Intermediate Similarity	NPC136188
0.84	Intermediate Similarity	NPC304309
0.84	Intermediate Similarity	NPC230301

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 NPC178383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	1920
0.2-0.3	4352
0.3-0.4	2004
0.4-0.5	352
0.5-0.6	177
0.6-0.7	172
0.7-0.8	53
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5247	Approved

Showing 1 to 5 of 200 entries

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Structure

CID178383 OpenBabel06191715552D 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 1 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 1 1 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	72326
ChEMBL	CHEMBL23236
ZINC

Physicochemical Properties

Molecular Weight:	442.38
ALogP:	2.1406
MLogP:	4.54
XLogP:	9.714
# Rotatable Bonds:	10
Polar Surface Area:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	32

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