NPASS Natural Product

Natural Product: NPC33768

Natural Product ID:	NPC33768
Common Name:	3Alpha,27-Dihydroxylup-20(29)-En-28-Oic Acid Methyl Ester
IUPAC Name:	methyl (1R,3aS,5aS,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-hydroxy-5a-(hydroxymethyl)-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
Synonyms:
Molecular Formula:	C31H50O4
Standard InCHIKey:	UEBDDJDCLTYODS-VAPIBPPKSA-N
Standard InCHI:	InChI=1S/C31H50O4/c1-19(2)20-10-15-30(26(34)35-7)16-17-31(18-32)21(25(20)30)8-9-23-28(5)13-12-24(33)27(3,4)22(28)11-14-29(23,31)6/h20-25,32-33H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24+,25+,28-,29+,30-,31-/m0/s1
Canonical SMILES:	COC(=O)[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(CO)[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
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota				PMID[10757727]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	8900	nM	20599387

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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 NPC33768 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	116
0.1-0.2	876
0.2-0.3	3426
0.3-0.4	10385
0.4-0.5	5898
0.5-0.6	3717
0.6-0.7	3637
0.7-0.8	2227
0.8-0.85	418
0.85-0.9	150
0.9-0.95	27
0.95-1	12

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Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC470385
0.8471	Intermediate Similarity	NPC30583
0.8471	Intermediate Similarity	NPC472504
0.8471	Intermediate Similarity	NPC170985
0.8478	Intermediate Similarity	NPC234564

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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 NPC33768 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	1569
0.2-0.3	3899
0.3-0.4	2365
0.4-0.5	661
0.5-0.6	202
0.6-0.7	200
0.7-0.8	115
0.8-0.85	11
0.85-0.9	2
0.9-0.95	2
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6696	Remote Similarity	NPD5983	Phase 2
0.6696	Remote Similarity	NPD6291	Clinical (unspecified phase)

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Structure

NPC33768 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 3.8710 -1.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2649 -1.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3525 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8650 -1.1056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4687 3.5452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1891 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6160 1.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9173 -1.2286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6160 -0.3013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3775 -2.9250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6887 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2922 1.8657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -1.9500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -3.4125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3225 1.9676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8653 2.6545 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 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 7 35 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 28 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 30 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 20 19 1 1 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 1 0 0 0 22 27 1 0 0 0 0 22 28 1 6 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 30 1 6 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 28 5 1 6 0 0 0 29 31 1 1 0 0 0 30 26 1 6 0 0 0 31 18 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	11799152
ChEMBL	CHEMBL525784
ZINC

Physicochemical Properties

Molecular Weight:	486.37
ALogP:	1.5098
MLogP:	4.43
XLogP:	7.541
# Rotatable Bonds:	12
Polar Surface Area:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	35

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