NPASS Natural Product

Natural Product: NPC15083

Natural Product ID:	NPC15083
Common Name:	Oleoylbitalin A
IUPAC Name:	2-[(2R)-5-acetyl-2,3-dihydro-1-benzofuran-2-yl]prop-2-enyl (Z)-octadec-9-enoate
Synonyms:	Oleoylbitalin A
Molecular Formula:	C31H46O4
Standard InCHIKey:	XHZDCOHEWFWFQX-FNFBAFLYSA-N
Standard InCHI:	InChI=1S/C31H46O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-31(33)34-24-25(2)30-23-28-22-27(26(3)32)20-21-29(28)35-30/h11-12,20-22,30H,2,4-10,13-19,23-24H2,1,3H3/b12-11-/t30-/m1/s1
Canonical SMILES:	CCCCCCCC/C=CCCCCCCCC(=O)OCC(=C)[C@H]1Cc2c(O1)ccc(c2)C(=O)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
NPO25148.1	Helichrysum italicum	Under-species	NA	NA	Flowered aerial parts	Arzana, Sardinia	2010-JUL	PMID[23265253]

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Biological Activity

Activity Type	# Activity
MIC	6

Activity Type	# Activity
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	>	128	ug/ml	17887721
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	26425784
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	19540629
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	21477899
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	DrugMatrix in vitro pharmacology data

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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 NPC15083 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	218
0.1-0.2	1098
0.2-0.3	2099
0.3-0.4	4709
0.4-0.5	8082
0.5-0.6	3422
0.6-0.7	5750
0.7-0.8	5157
0.8-0.85	327
0.85-0.9	16
0.9-0.95	4
0.95-1	7

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Similarity Score	Similarity Level	Natural Product ID
0.8085	Intermediate Similarity	NPC307883
0.8092	Intermediate Similarity	NPC74749
0.8092	Intermediate Similarity	NPC43971
0.8092	Intermediate Similarity	NPC49009
0.8092	Intermediate Similarity	NPC19554

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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 NPC15083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	907
0.2-0.3	1309
0.3-0.4	2285
0.4-0.5	2229
0.5-0.6	1338
0.6-0.7	639
0.7-0.8	211
0.8-0.85	20
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
0.7059	Intermediate Similarity	NPD1511	Approved
0.7059	Intermediate Similarity	NPD8434	Phase 2
0.7063	Intermediate Similarity	NPD454	Approved
0.7067	Intermediate Similarity	NPD5958	Discontinued
0.7067	Intermediate Similarity	NPD4534	Discontinued

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Structure

NPC15083 OpenBabel07101719252D 35 36 0 0 1 0 0 0 0 0999 V2000 -15.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0878 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0878 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 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 25 2 0 0 0 0 3 26 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 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 2 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 31 1 0 0 0 0 20 21 2 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 0 0 0 0 26 27 1 0 0 0 0 26 32 2 0 0 0 0 28 29 2 0 0 0 0 29 35 1 0 0 0 0 30 25 1 6 0 0 0 30 35 1 0 0 0 0 31 33 2 0 0 0 0 31 34 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	71659266
ChEMBL	CHEMBL2334421
ZINC

Physicochemical Properties

Molecular Weight:	482.34
ALogP:	-2.0665
MLogP:	4.43
XLogP:	10.235
# Rotatable Bonds:	22
Polar Surface Area:	52.6
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	35

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