NPASS Natural Product

Natural Product: NPC28657

Natural Product ID:	NPC28657
Common Name:	Cholesterol
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-ol
Synonyms:	Cholesterin; Cholesterol; Cholestrin
Molecular Formula:	C27H46O
Standard InCHIKey:	HVYWMOMLDIMFJA-DPAQBDIFSA-N
Standard InCHI:	InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
Canonical SMILES:	CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)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	Reference
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	UNPD*
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	UNPD*
NPO10327	Laurencia aldingensis	Species	Rhodomelaceae	Eukaryota	UNPD*
NPO10341	Pseudogymnoascus pannorum	Species	Pseudeurotiaceae	Eukaryota	UNPD*
NPO10508	Gossypium sturtianum	Species	Malvaceae	Eukaryota	UNPD*
NPO1054	Peucedanum graveolens	Species	Apiaceae	Eukaryota	UNPD*
NPO10623	Melo semen	Species	Volutidae	Eukaryota	TCMSP*
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	UNPD*
NPO10770	Ptilota pectinata	Species	Ceramiaceae	Eukaryota	UNPD*
NPO10954	Topsentia genitrix	Species	NA	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	12
MIC	7
Others	29
Potency	5

Activity Type	# Activity
Cell Line	6
Individual Protein	25
Organism	20
Protein Family	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency		79432.8	nM	PubChem BioAssay data set
NPT1160	Cell Line	BJ	Homo sapiens	IC50	>	50000	nM	22417637
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	7.8	mm	18455270
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	7.8	mm	18294737
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	512	ug/ml	18294737
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	50000	nM	19473028
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		54482.7	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency		39810.7	nM	PubChem BioAssay data set
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9.2	mm	18455270
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9.2	mm	18294737

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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 NPC28657 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	95
0.1-0.2	878
0.2-0.3	3868
0.3-0.4	11615
0.4-0.5	5766
0.5-0.6	3959
0.6-0.7	3185
0.7-0.8	1104
0.8-0.85	207
0.85-0.9	114
0.9-0.95	67
0.95-1	31

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Similarity Score	Similarity Level	Natural Product ID
0.8519	High Similarity	NPC58063
0.8519	High Similarity	NPC475313
0.8533	High Similarity	NPC120098
0.8533	High Similarity	NPC265328
0.8533	High Similarity	NPC315261

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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 NPC28657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	1321
0.2-0.3	4200
0.3-0.4	2409
0.4-0.5	639
0.5-0.6	179
0.6-0.7	187
0.7-0.8	67
0.8-0.85	9
0.85-0.9	16
0.9-0.95	1
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6505	Remote Similarity	NPD5249	Phase 3
0.6505	Remote Similarity	NPD5169	Approved
0.6505	Remote Similarity	NPD5248	Approved
0.6505	Remote Similarity	NPD5250	Approved
0.6505	Remote Similarity	NPD5251	Approved

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Structure

CID28657 OpenBabel06191715352D 28 31 0 0 1 0 0 0 0 0999 V2000 -3.9926 6.3752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5325 5.6891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8042 3.7080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5322 2.4699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7403 3.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1684 4.6985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3441 3.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8434 -1.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6874 -0.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2183 1.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2180 0.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8431 0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6882 1.9476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 -1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5645 5.5876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3761 2.9204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6867 -0.9738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3758 1.9471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5316 0.4864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8440 0.4869 0.0000 C 0 0 1 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 -2.5319 1.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5529 -1.4736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 28 1 6 0 0 0 22 10 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 27 1 6 0 0 0 24 27 1 6 0 0 0 25 26 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	5997
ChEMBL	CHEMBL112570
ZINC

Physicochemical Properties

Molecular Weight:	386.35
ALogP:	1.5548
MLogP:	4.32
XLogP:	10.518
# Rotatable Bonds:	11
Polar Surface Area:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	28

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