NPASS Natural Product

Natural Product: NPC36491

Natural Product ID:	NPC36491
Common Name:	Simvastatin
IUPAC Name:	[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
Synonyms:	Lacersa; MK-733; Ranzolont; Simvador; Simvastatin; Simvastatin hydroxy acid; Synvinolin; Zocor; Zocor Heart-Pro
Molecular Formula:	C25H38O5
Standard InCHIKey:	RYMZZMVNJRMUDD-HGQWONQESA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
Canonical SMILES:	CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)(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	Isolation Part	Collection Location	Collection Time	Reference
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood			PMID[14691614]

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Biological Activity

Activity Type	# Activity
AC50	3
ED50	2
GI50	51
IC50	64
Ki	6
Others	46
Potency	100

Activity Type	# Activity
Cell Line	68
Individual Protein	67
Organism	39
Others	98

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		58	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		5804.8	nM	PubChem BioAssay data set
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	Activity	=	-19	%	16384704
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	Activity	=	18.4	%	19530681
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency		30895.6	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	30000	nM	22328583
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	30000	nM	22328583
NPT111	Cell Line	K562	Homo sapiens	GI50		17579.24	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		29991.63	nM	PubChem BioAssay data set
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	IC50	=	4	nM	17574411

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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 NPC36491 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	123
0.1-0.2	596
0.2-0.3	2454
0.3-0.4	5140
0.4-0.5	10959
0.5-0.6	5112
0.6-0.7	4871
0.7-0.8	1613
0.8-0.85	17
0.85-0.9	1
0.9-0.95	2
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.7624	Intermediate Similarity	NPC473514
0.7629	Intermediate Similarity	NPC477436
0.7629	Intermediate Similarity	NPC474806
0.7629	Intermediate Similarity	NPC298554
0.7629	Intermediate Similarity	NPC477435

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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 NPC36491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	908
0.2-0.3	3366
0.3-0.4	2920
0.4-0.5	1163
0.5-0.6	335
0.6-0.7	271
0.7-0.8	59
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	3

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6413	Remote Similarity	NPD7152	Approved
0.6413	Remote Similarity	NPD7151	Approved
0.6415	Remote Similarity	NPD7614	Phase 1
0.6417	Remote Similarity	NPD5988	Approved
0.6421	Remote Similarity	NPD6932	Approved

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Structure

CID36491 OpenBabel06191715362D 30 32 0 0 1 0 0 0 0 0999 V2000 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 4.8301 2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 3.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 2.5981 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 5.1962 2.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 1 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 0.0000 2.0000 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 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 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 4.3301 3.5000 0.0000 C 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 2 1 1 0 0 0 16 3 1 6 0 0 0 16 20 1 0 0 0 0 18 26 1 6 0 0 0 19 9 1 1 0 0 0 19 29 1 0 0 0 0 20 10 1 6 0 0 0 20 23 1 0 0 0 0 21 23 1 0 0 0 0 21 30 1 1 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 23 17 1 1 0 0 0 24 25 1 0 0 0 0 24 28 2 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	54454
ChEMBL	CHEMBL1064
ZINC

Physicochemical Properties

Molecular Weight:	418.27
ALogP:	1.0638
MLogP:	3.66
XLogP:	4.775
# Rotatable Bonds:	13
Polar Surface Area:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	30

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