NPASS Natural Product

Natural Product: NPC35269

Natural Product ID:	NPC35269
Common Name:	Alternaroside B
IUPAC Name:	(E,2R)-2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-9-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptadeca-4,8-dien-2-yl]octadec-3-enamide
Synonyms:	alternaroside B
Molecular Formula:	C42H77NO9
Standard InCHIKey:	XYCVJZWQEQFSGR-MXVOGVNUSA-N
Standard InCHI:	InChI=1S/C42H77NO9/c1-4-6-8-10-12-13-14-15-16-17-18-19-21-25-30-36(46)41(50)43-34(32-51-42-40(49)39(48)38(47)37(31-44)52-42)35(45)29-26-22-24-28-33(3)27-23-20-11-9-7-5-2/h25-26,28-30,34-40,42,44-49H,4-24,27,31-32H2,1-3H3,(H,43,50)/b29-26+,30-25+,33-28+/t34-,35+,36+,37+,38+,39-,40+,42+/m0/s1
Canonical SMILES:	CCCCCCCCCCCCCC/C=C/[C@H](C(=N[C@H]([C@@H](/C=C/CC/C=C(/CCCCCCCC)C)O)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)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	Isolation Part	Collection Location	Collection Time	Reference
NPO32519	alternaria raphani	Species	Pleosporaceae	Eukaryota				PMID[19685913]

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Biological Activity

Activity Type	# Activity
IC50	5
MIC	3

Activity Type	# Activity
Cell Line	4
Organism	3
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	500000	nM	18172002
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000	nM	24063567
NPT168	Cell Line	P388	Mus musculus	IC50	>	100000	nM	DrugMatrix in vitro pharmacology data
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000	nM	1431942
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	135000	nM	18172002
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	270000	nM	DrugMatrix in vitro pharmacology data
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	68000	nM	25651042
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000	nM	10560746

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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 NPC35269 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	51
0.1-0.2	431
0.2-0.3	4337
0.3-0.4	15056
0.4-0.5	7842
0.5-0.6	2845
0.6-0.7	264
0.7-0.8	27
0.8-0.85	1
0.85-0.9	3
0.9-0.95	10
0.95-1	22

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Similarity Score	Similarity Level	Natural Product ID
0.6237	Remote Similarity	NPC223174
0.6237	Remote Similarity	NPC327486
0.6237	Remote Similarity	NPC327753
0.6239	Remote Similarity	NPC60432
0.6239	Remote Similarity	NPC474194

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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 NPC35269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	68
0.1-0.2	367
0.2-0.3	4053
0.3-0.4	3503
0.4-0.5	946
0.5-0.6	192
0.6-0.7	29
0.7-0.8	2
0.8-0.85	0
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
0.5625	Remote Similarity	NPD7844	Discontinued
0.563	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.563	Remote Similarity	NPD6686	Approved
0.567	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD6914	Discontinued

Showing 1 to 5 of 59 entries

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Structure

NPC35269 OpenBabel07101718202D 52 52 0 0 1 0 0 0 0 0999 V2000 9.5263 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 4 1 0 0 0 0 2 5 1 0 0 0 0 3 33 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 30 2 0 0 0 0 26 29 2 0 0 0 0 27 33 1 0 0 0 0 28 33 2 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 44 1 0 0 0 0 32 51 1 0 0 0 0 34 32 1 1 0 0 0 34 35 1 0 0 0 0 34 43 1 0 0 0 0 35 45 1 1 0 0 0 36 41 1 0 0 0 0 36 46 1 6 0 0 0 37 31 1 6 0 0 0 37 38 1 0 0 0 0 37 52 1 0 0 0 0 38 39 1 0 0 0 0 38 47 1 1 0 0 0 39 40 1 0 0 0 0 39 48 1 6 0 0 0 40 42 1 0 0 0 0 40 49 1 1 0 0 0 41 43 2 3 0 0 0 41 50 1 0 0 0 0 42 51 1 6 0 0 0 42 52 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44478681
ChEMBL	CHEMBL1078815
ZINC

Physicochemical Properties

Molecular Weight:	739.56
ALogP:	-5.9702
MLogP:	4.98
XLogP:	11.906
# Rotatable Bonds:	42
Polar Surface Area:	172.43
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	1
# Heavy Atoms:	52

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