NPASS Natural Product

Natural Product: NPC265557

Natural Product ID:	NPC265557
Common Name:	Bruceantin
IUPAC Name:
Synonyms:	Bruceantin; Bruceantine
Molecular Formula:	C28H36O11
Standard InCHIKey:	IRQXZTBHNKVIRL-GOTQHHPNSA-N
Standard InCHI:	InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1
Canonical SMILES:	COC(=O)[C@@]12OC[C@]34[C@H]2[C@@H](OC(=O)/C=C(/C(C)C)C)C(=O)O[C@@H]4C[C@@H]2[C@]([C@H]3[C@H]([C@@H]1O)O)(C)CC(=O)C(=C2C)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
NPO10818	Carpobrotus edulis	Species	Aizoaceae	Eukaryota	UNPD*
NPO11084	Asplenium normale	Species	Aspleniaceae	Eukaryota	UNPD*
NPO11432	Centrolobium tomentosum	Species	Fabaceae	Eukaryota	UNPD*
NPO11637	Psilostrophe cooperi	Species	Asteraceae	Eukaryota	UNPD*
NPO11873	Oecophylla smaragdina	Species	Formicidae	Eukaryota	UNPD*
NPO12089	Trifolium alexandrinum	Species	Fabaceae	Eukaryota	UNPD*
NPO12717	Parmelia metastrigosa	Species	Parmeliaceae	Eukaryota	UNPD*
NPO12944	Sideritis tragoriganum	Species	Lamiaceae	Eukaryota	UNPD*
NPO14150	Solanum jamaicense	Species	Solanaceae	Eukaryota	UNPD*
NPO14528	Pneumatospora obcoronata	NA	NA	NA	UNPD*

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Biological Activity

Activity Type	# Activity
EC50	1
ED50	5
GI50	74
IC50	21
Others	5

Activity Type	# Activity
Cell Line	96
Individual Protein	2
Organism	2
Others	6

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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	=	12	nM	19026551
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	=	514000	nM	15481972
NPT111	Cell Line	K562	Homo sapiens	Activity	=	90	%	14987068
NPT111	Cell Line	K562	Homo sapiens	GI50		20	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		20	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	40	nM	11754601
NPT116	Cell Line	HL-60	Homo sapiens	EC50	=	20	nM	11754601
NPT116	Cell Line	HL-60	Homo sapiens	Ratio IC50	=	1		11754601
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.02	ug/ml	14987068
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	12.2	nM	14987068

Showing 1 to 10 of 103 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 NPC265557 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	178
0.1-0.2	933
0.2-0.3	2620
0.3-0.4	4439
0.4-0.5	6542
0.5-0.6	8515
0.6-0.7	4558
0.7-0.8	2594
0.8-0.85	381
0.85-0.9	77
0.9-0.95	44
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.8347	Intermediate Similarity	NPC268958
0.8348	Intermediate Similarity	NPC202524
0.8361	Intermediate Similarity	NPC275675
0.8361	Intermediate Similarity	NPC472000
0.8361	Intermediate Similarity	NPC4021

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 NPC265557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1362
0.2-0.3	3444
0.3-0.4	2616
0.4-0.5	885
0.5-0.6	408
0.6-0.7	163
0.7-0.8	99
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6407	Remote Similarity	NPD8368	Discontinued
0.6412	Remote Similarity	NPD5127	Approved
0.6435	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5169	Approved
0.6462	Remote Similarity	NPD5134	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID265557 OpenBabel06191716062D 39 43 0 0 1 0 0 0 0 0999 V2000 5.8153 3.7378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2373 2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9146 4.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4119 3.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7374 0.5241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6735 -2.0798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3366 2.7591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1407 2.6284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3752 1.1592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3113 0.9579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0511 3.0816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1008 3.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3969 2.6096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7634 2.2564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0086 1.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4928 2.2752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5228 1.7692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0195 2.2376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2164 0.4592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8083 1.4467 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1190 1.1780 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3185 0.9579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2849 -0.0650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7315 2.1343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8596 -0.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7525 1.5312 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5036 1.5500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0072 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8733 0.9958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4732 1.4355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8992 2.7282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1743 0.1480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0691 -1.0080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5850 2.6693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7506 -0.0667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8211 -1.5431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1461 2.5030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7586 1.1130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 6 36 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 26 1 0 0 0 0 10 37 1 0 0 0 0 11 12 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 26 1 6 0 0 0 15 18 1 0 0 0 0 15 29 2 0 0 0 0 16 27 1 1 0 0 0 16 38 1 0 0 0 0 17 30 2 0 0 0 0 17 39 1 0 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 6 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 20 39 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 23 28 1 1 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 38 1 0 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 5 1 6 0 0 0 27 10 1 6 0 0 0 28 25 1 6 0 0 0 28 37 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281304
ChEMBL	CHEMBL509895
ZINC

Physicochemical Properties

Molecular Weight:	548.23
ALogP:	-0.4629
MLogP:	3.33
XLogP:	1.867
# Rotatable Bonds:	15
Polar Surface Area:	165.89
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	39

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