NPASS Natural Product

Natural Product: NPC105493

Natural Product ID:	NPC105493
Common Name:	4-Acetoxy-2-Geranyl-5-Hydroxy-3-N-Pentylphenol
IUPAC Name:	[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4,6-dihydroxy-2-pentylphenyl] acetate
Synonyms:
Molecular Formula:	C23H34O4
Standard InCHIKey:	DZLSXQDQGMAPKJ-GHRIWEEISA-N
Standard InCHI:	InChI=1S/C23H34O4/c1-6-7-8-12-20-19(14-13-17(4)11-9-10-16(2)3)21(25)15-22(26)23(20)27-18(5)24/h10,13,15,25-26H,6-9,11-12,14H2,1-5H3/b17-13+
Canonical SMILES:	CCCCCc1c(C/C=C(/CCC=C(C)C)C)c(O)cc(c1OC(=O)C)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
NPO7513	Cannabis sativa	Species	Cannabaceae	Eukaryota				PMID[19344127]

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Biological Activity

Activity Type	# Activity
IC50	4
Others	1

Activity Type	# Activity
Organism	5

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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	IC50	=	12200	nM	DrugMatrix in vitro pharmacology data
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	6700	nM	22220635
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IC50	=	53400	nM	20055495
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	42700	nM	20055495
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	85400	nM	19459643

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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 NPC105493 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	252
0.1-0.2	1176
0.2-0.3	2841
0.3-0.4	7207
0.4-0.5	6050
0.5-0.6	2509
0.6-0.7	5310
0.7-0.8	4751
0.8-0.85	662
0.85-0.9	124
0.9-0.95	6
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.8403	Intermediate Similarity	NPC474104
0.8403	Intermediate Similarity	NPC472451
0.8403	Intermediate Similarity	NPC102044
0.8406	Intermediate Similarity	NPC15543
0.8406	Intermediate Similarity	NPC82503

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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 NPC105493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	898
0.2-0.3	1842
0.3-0.4	2768
0.4-0.5	1684
0.5-0.6	960
0.6-0.7	596
0.7-0.8	136
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6821	Remote Similarity	NPD2674	Phase 3
0.6826	Remote Similarity	NPD5677	Discontinued
0.6829	Remote Similarity	NPD4585	Approved
0.6831	Remote Similarity	NPD5536	Phase 2
0.6835	Remote Similarity	NPD6667	Approved

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Structure

NPC105493 OpenBabel07101718222D 27 27 0 0 0 0 0 0 0 0999 V2000 3.4641 0.0000 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 -2.5981 -7.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 1.7321 -1.0000 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 -6.0000 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 0.8660 -1.5000 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 -0.8660 -2.5000 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 -7.0000 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 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 0.0000 -1.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 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 -2.5981 -1.5000 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 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 20 2 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 23 2 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44139611
ChEMBL	CHEMBL560417
ZINC

Physicochemical Properties

Molecular Weight:	374.25
ALogP:	1.3575
MLogP:	3.55
XLogP:	6.327
# Rotatable Bonds:	18
Polar Surface Area:	66.76
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	27

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