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Surfactin D

PubChem CID
70789015
Structure
Surfactin D_small.png
Molecular Formula
Synonyms
  • surfactin D
  • CHEBI:71979
  • 3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-3,6,15,18-tetraisobutyl-12-isopropyl-25-(11-methyldodecyl)-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-21-yl]propanoic acid
  • 3-((3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-25-(11-methyldodecyl)-3,6,15,18-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-12-propan-2-yl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl)propanoic acid
  • 3-((3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-3,6,15,18-tetraisobutyl-12-isopropyl-25-(11-methyldodecyl)-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-21-yl)propanoic acid
Molecular Weight
1050.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2013-03-05
  • Modify:
    2024-12-07
Description
Surfactin D is a cyclodepsipeptide that is N-[(3R)-3-hydroxy-14-methylpentadecanoyl]-L-alpha-glutamyl-L-leucyl-D-leucyl-L-valyl-L-alpha-aspartyl-D-leucyl-L-leucine in which the C-terminal carboxy group has been lactonised by condensation with the alcoholic hydroxy group. It has a role as an antibacterial agent, an antifungal agent, an antiviral agent, a surfactant, a metabolite and an antineoplastic agent. It is a cyclodepsipeptide, a lipopeptide antibiotic and a macrocyclic lactone.
surfactin D has been reported in Bacillus subtilis with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Surfactin D.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
cyclo[Asp-D-Leu-Leu-ObAla(3R-isotridecyl)-Glu-Leu-D-Leu-Val]
HELM
PEPTIDE1{D.[dL].L.[*C(=O)C[C@@H](CCCCCCCCCCC(C)C)O* |$_R2;;;;;;;;;;;;;;;;;;;_R1$|].E.L.[dL].V}$PEPTIDE1,PEPTIDE1,8:R2-1:R1$$$
IUPAC
cyclo[L-alpha-aspartyl-D-leucyl-L-leucyl-N-oxa-(3R)-3-isotridecyl-beta-alanyl-L-alpha-glutamyl-L-leucyl-D-leucyl-L-valyl]

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

3-[(3S,6R,9S,12S,15R,18S,21S,25R)-9-(carboxymethyl)-25-(11-methyldodecyl)-3,6,15,18-tetrakis(2-methylpropyl)-2,5,8,11,14,17,20,23-octaoxo-12-propan-2-yl-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-21-yl]propanoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C54H95N7O13/c1-31(2)21-19-17-15-13-14-16-18-20-22-37-29-44(62)55-38(23-24-45(63)64)48(67)56-39(25-32(3)4)49(68)58-41(27-34(7)8)52(71)61-47(36(11)12)53(72)59-42(30-46(65)66)51(70)57-40(26-33(5)6)50(69)60-43(28-35(9)10)54(73)74-37/h31-43,47H,13-30H2,1-12H3,(H,55,62)(H,56,67)(H,57,70)(H,58,68)(H,59,72)(H,60,69)(H,61,71)(H,63,64)(H,65,66)/t37-,38+,39+,40-,41-,42+,43+,47+/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

HPBKRTWLUQRMNA-PTYDTDROSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

CC(C)CCCCCCCCCC[C@@H]1CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)O1)CC(C)C)CC(C)C)CC(=O)O)C(C)C)CC(C)C)CC(C)C)CCC(=O)O
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)

3.2 Molecular Formula

C54H95N7O13
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 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
1050.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
9.4
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
9
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
13
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
25
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
1049.69878611 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
1049.69878611 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
305Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
74
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1820
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
8
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 2019.01.04)

5 Spectral Information

5.1 Mass Spectrometry

5.1.1 LC-MS

MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
1050.71
Instrument
Orbitrap
Ionization Mode
positive
Top 5 Peaks

86.096596 100

199.180603 30.18

201.123871 19.90

227.175964 19.58

84.044640 18.80

Thumbnail
Thumbnail

7 Literature

7.1 Consolidated References

8 Patents

8.1 Depositor-Supplied Patent Identifiers

9 Taxonomy

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

10 Classification

10.1 ChEBI Ontology

10.2 LOTUS Tree

10.3 MolGenie Organic Chemistry Ontology

11 Information Sources

CONTENTS