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Hikiamide B

PubChem CID
139588724
Structure
Hikiamide B_small.png
Hikiamide B_3D_Structure.png
Molecular Formula
Synonyms
  • Hikiamide B
  • CHEBI:219044
  • (3R,6R,9R,12R,15R)-6,9-dibenzyl-1-methyl-3,12-bis(2-methylpropyl)-15-propan-2-yl-1,4,7,10,13-pentazacyclopentadecane-2,5,8,11,14-pentone
Molecular Weight
633.8 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2019-11-04
  • Modify:
    2024-12-07
Description
Hikiamide B is a cyclic peptide.
cyclo[D-Leu-D-Phe-D-Phe-D-Leu-D-N(Me)Val] has been reported in Fusarium with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Hikiamide B.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
cyclo[D-Leu-D-Phe-D-Phe-D-Leu-D-N(Me)Val]
HELM
PEPTIDE1{[dL].[dF].[dF].[dL].[*C(=O)[C@@H](C(C)C)N(*)C |$_R2;;;;;;;;_R1;$|]}$PEPTIDE1,PEPTIDE1,5:R2-1:R1$$$
IUPAC
cyclo[D-leucyl-D-phenylalanyl-D-phenylalanyl-D-leucyl-N-methyl-D-valyl]

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(3R,6R,9R,12R,15R)-6,9-dibenzyl-1-methyl-3,12-bis(2-methylpropyl)-15-propan-2-yl-1,4,7,10,13-pentazacyclopentadecane-2,5,8,11,14-pentone
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C36H51N5O5/c1-22(2)18-27-32(42)37-28(20-25-14-10-8-11-15-25)33(43)38-29(21-26-16-12-9-13-17-26)34(44)40-30(19-23(3)4)36(46)41(7)31(24(5)6)35(45)39-27/h8-17,22-24,27-31H,18-21H2,1-7H3,(H,37,42)(H,38,43)(H,39,45)(H,40,44)/t27-,28-,29-,30-,31-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

HKBRDPGBCQZFAU-JQWMYKLHSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

CC(C)C[C@@H]1C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N([C@@H](C(=O)N1)C(C)C)C)CC(C)C)CC2=CC=CC=C2)CC3=CC=CC=C3
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)

3.2 Molecular Formula

C36H51N5O5
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 ChEBI ID

3.3.2 Metabolomics Workbench ID

3.3.3 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

hikiamide B

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
633.8 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
5.7
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
633.38901974 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
633.38901974 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
137Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
46
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1030
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.06.18)

6 Literature

6.1 Consolidated References

6.2 NLM Curated PubMed Citations

7 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

8 Classification

8.1 MeSH Tree

8.2 ChEBI Ontology

8.3 The Natural Products Atlas Classification

8.4 LOTUS Tree

8.5 MolGenie Organic Chemistry Ontology

9 Information Sources

  1. ChEBI
  2. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    cyclo[D-Leu-D-Phe-D-Phe-D-Leu-D-N(Me)Val]
    https://www.wikidata.org/wiki/Q105029578
  3. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  4. Metabolomics Workbench
  5. Wikidata
    cyclo[D-Leu-D-Phe-D-Phe-D-Leu-D-N(Me)Val]
    https://www.wikidata.org/wiki/Q105029578
  6. PubChem
  7. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  8. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS