NPASS Natural Product

Natural Product: NPC264127

Natural Product ID:	NPC264127
Common Name:	Cholesteryl Oleate
IUPAC Name:	[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate
Synonyms:	Cholesteryl Oleate
Molecular Formula:	C45H78O2
Standard InCHIKey:	RJECHNNFRHZQKU-RMUVNZEASA-N
Standard InCHI:	InChI=1S/C45H78O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
Canonical SMILES:	CCCCCCCC/C=CCCCCCCCC(=O)O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCCC(C)C)C)C)C1)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	Reference
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota		DOI[10.1038/nbt.2488]
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood	PMID[21359215]
NPO20338	Mus musculus	Species	Muridae	Eukaryota		PMID[25518943]

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Biological Activity

Activity Type	# Activity
MIC	10
Others	10

Activity Type	# Activity
Organism	20

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1190	Organism	Salmonella enterica	Salmonella enterica	IZ	=	15.1	mm	20106564
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	128	ug/ml	20106564
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	17.2	mm	20106564
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	64	ug/ml	20106564
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	17.8	mm	20106564
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64	ug/ml	20106564
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	14.3	mm	20106564
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128	ug/ml	20106564
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IZ	=	16.8	mm	20106564
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	256	ug/ml	20106564

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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 NPC264127 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	135
0.1-0.2	740
0.2-0.3	3018
0.3-0.4	9376
0.4-0.5	6854
0.5-0.6	4223
0.6-0.7	4310
0.7-0.8	1958
0.8-0.85	229
0.85-0.9	40
0.9-0.95	4
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.8068	Intermediate Similarity	NPC470048
0.8068	Intermediate Similarity	NPC469948
0.8072	Intermediate Similarity	NPC69143
0.8072	Intermediate Similarity	NPC899
0.8081	Intermediate Similarity	NPC472218

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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 NPC264127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1081
0.2-0.3	3703
0.3-0.4	2784
0.4-0.5	827
0.5-0.6	267
0.6-0.7	193
0.7-0.8	138
0.8-0.85	7
0.85-0.9	12
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6754	Remote Similarity	NPD6909	Approved
0.6754	Remote Similarity	NPD6908	Approved
0.6768	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD5778	Approved
0.6771	Remote Similarity	NPD4751	Clinical (unspecified phase)

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Structure

CID264127 OpenBabel06191716062D 47 50 0 0 1 0 0 0 0 0999 V2000 -11.3837 -1.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0349 6.4426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5911 5.7492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8339 3.7472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5589 2.4960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3834 -2.4159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5310 -2.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6788 -2.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8264 -2.9072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9743 -2.4149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1219 -2.9068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2697 -2.4144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4173 -2.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5651 -2.4140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7127 -2.9058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8606 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0081 -2.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1560 -2.4130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3036 -2.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5486 -2.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7904 3.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2125 4.7482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3901 3.0538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4010 -2.9043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8523 -1.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7052 -0.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2629 1.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2627 0.4911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7043 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8532 1.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8520 0.4926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7060 1.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8526 -1.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6128 5.6467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4118 2.9513 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7046 -0.9841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7055 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4115 1.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5584 0.4916 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8529 0.4921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2532 -2.4120 0.0000 C 0 0 0 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 -2.5586 1.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9119 -3.1432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5570 -1.4760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 35 1 0 0 0 0 3 35 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 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 21 1 0 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 43 1 0 0 0 0 26 27 1 0 0 0 0 26 37 2 0 0 0 0 28 29 1 0 0 0 0 28 40 1 0 0 0 0 29 41 1 0 0 0 0 30 32 1 0 0 0 0 30 38 1 0 0 0 0 31 33 1 0 0 0 0 31 42 1 0 0 0 0 32 44 1 0 0 0 0 33 45 1 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 36 4 1 1 0 0 0 36 40 1 0 0 0 0 37 44 1 0 0 0 0 38 47 1 6 0 0 0 39 27 1 1 0 0 0 39 41 1 0 0 0 0 39 42 1 0 0 0 0 40 45 1 6 0 0 0 41 45 1 6 0 0 0 42 44 1 6 0 0 0 43 46 2 0 0 0 0 43 47 1 0 0 0 0 44 5 1 6 0 0 0 45 6 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	5283632
ChEMBL	CHEMBL1097567
ZINC

Physicochemical Properties

Molecular Weight:	650.60
ALogP:	-0.1789
MLogP:	6.19
XLogP:	19.53
# Rotatable Bonds:	28
Polar Surface Area:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	47

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