NPASS Natural Product

Natural Product: NPC23454

Natural Product ID:	NPC23454
Common Name:	Chrysogeside D
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]nonadec-3-enamide
Synonyms:	Chrysogeside D
Molecular Formula:	C43H79NO9
Standard InCHIKey:	SSNZBMSHTYMPDC-DDSPGNMTSA-N
Standard InCHI:	InChI=1S/C43H79NO9/c1-4-6-8-10-12-13-14-15-16-17-18-19-20-22-26-31-37(47)42(51)44-35(33-52-43-41(50)40(49)39(48)38(32-45)53-43)36(46)30-27-23-25-29-34(3)28-24-21-11-9-7-5-2/h26-27,29-31,35-41,43,45-50H,4-25,28,32-33H2,1-3H3,(H,44,51)/b30-27+,31-26+,34-29+/t35-,36+,37+,38+,39+,40-,41+,43+/m0/s1
Canonical SMILES:	CCCCCCCCCCCCCCC/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
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	mycelium			PMID[21381678]

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Biological Activity

Activity Type	# Activity
IC50	2
MIC	6

Activity Type	# Activity
Cell Line	2
Organism	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	150000	nM	21381678
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000	nM	21381678
NPT168	Cell Line	P388	Mus musculus	IC50	>	50000	nM	21381678
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	150000	nM	21381678
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	150000	nM	21381678
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	150000	nM	21381678
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	150000	nM	21381678
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	150000	nM	21381678

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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 NPC23454 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 NPC23454 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

CID23454 OpenBabel06191715352D 53 53 0 0 1 0 0 0 0 0999 V2000 5.1962 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -3.4641 7.0000 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 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 N 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 -3.4641 3.0000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 34 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 21 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 20 1 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 26 31 2 0 0 0 0 27 30 2 0 0 0 0 28 34 1 0 0 0 0 29 34 2 0 0 0 0 30 36 1 0 0 0 0 31 37 1 0 0 0 0 32 45 1 0 0 0 0 33 52 1 0 0 0 0 35 33 1 6 0 0 0 35 36 1 0 0 0 0 35 44 1 0 0 0 0 36 46 1 6 0 0 0 37 42 1 0 0 0 0 37 47 1 6 0 0 0 38 32 1 1 0 0 0 38 39 1 0 0 0 0 38 53 1 0 0 0 0 39 40 1 0 0 0 0 39 48 1 6 0 0 0 40 41 1 0 0 0 0 40 49 1 1 0 0 0 41 43 1 0 0 0 0 41 50 1 6 0 0 0 42 44 2 3 0 0 0 42 51 1 0 0 0 0 43 52 1 1 0 0 0 43 53 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	53355905
ChEMBL	CHEMBL1802292
ZINC

Physicochemical Properties

Molecular Weight:	753.58
ALogP:	-6.2582
MLogP:	5.09
XLogP:	12.475
# Rotatable Bonds:	43
Polar Surface Area:	172.43
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	1
# Heavy Atoms:	53

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