NP-MRD: Showing NP-Card for (+)-Laurendecumallene A (NP0076771)

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Record Information

Version

2.0

Created at

2022-04-28 21:57:47 UTC

Updated at

2022-04-28 21:57:48 UTC

NP-MRD ID

NP0076771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Laurendecumallene A

Description

LAURENDECUMALLENE A belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. (+)-Laurendecumallene A is found in Laurencia decumbens. (+)-Laurendecumallene A was first documented in 2007 (PMID: 17711344). Based on a literature review very few articles have been published on LAURENDECUMALLENE A (PMID: 30600714).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -3.3660   -2.6787   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9249   -2.1631   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590   -0.9140    0.5459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5355   -0.3674    0.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -0.6349   -0.4109 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2944   -1.7366    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929   -0.9651    0.6402 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6794   -1.4814   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957   -0.6724   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7062    0.1772   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7401    0.0815    1.4983 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    0.3664    0.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392    0.4918   -0.5771 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7294    1.8437   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0992    2.2733    0.4626 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3227    3.5840    0.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634    2.3554    0.2245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1862    2.4675    1.4840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1898    1.2918   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7819    0.1411    0.1947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8127    0.7050    1.7217 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7972   -2.2410    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4016   -3.7666   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633   -2.4013   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -1.8816   -1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2863   -2.9856    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044   -1.2222    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0222   -0.9541   -1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5609   -2.4468   -0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8240   -2.3015    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5626   -1.1217    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -2.4342   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7754    0.7946   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913    0.2969   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    1.8736   -1.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942    2.5522   -0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    1.6882    1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021    4.2295    0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7609    3.3562   -0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    2.5675    2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0631    1.7438   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566    0.8527   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5166   -0.3636   -0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
  7  8  1  0
  8  9  2  0
  9 10  2  0
 10 11  1  0
 20  3  1  0
 13  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  1
  5 28  1  6
  6 29  1  0
  6 30  1  0
  7 31  1  1
 13 34  1  6
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  0
 17 39  1  6
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  6
  8 32  1  0
 10 33  1  0
M  END


  Mrv1652304282223572D          

 21 22  0  0  1  0            999 V2000
    1.7407    0.3182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9283    0.4615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    1.0934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3980    1.9184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9283    2.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407    2.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4552    2.2812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7374    1.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552    0.7307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0872    0.2004    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0872    2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8840    3.5062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3866    2.1734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716    1.5059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3866    0.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966    1.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1091    0.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5216    0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1091   -0.6375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.8840   -0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6593   -0.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  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
  1  9  1  0  0  0  0
  9 10  1  6  0  0  0
  7 11  1  6  0  0  0
  6 12  1  1  0  0  0
  4 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  1  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1O[C@@H]2C[C@H](O[C@@H]2C[C@@H](O)[C@H](O)C[C@@H]1Br)C=C=CBr

> <INCHI_IDENTIFIER>
InChI=1S/C15H22Br2O4/c1-2-13-10(17)7-11(18)12(19)8-15-14(21-13)6-9(20-15)4-3-5-16/h4-5,9-15,18-19H,2,6-8H2,1H3/t3?,9-,10+,11-,12-,13-,14-,15-/m1/s1

> <INCHI_KEY>
BYNNASQGMHJTHX-JFPGLQQHSA-N

> <FORMULA>
C15H22Br2O4

> <MOLECULAR_WEIGHT>
426.145

> <EXACT_MASS>
423.988485

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.06340686120248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3aR,5R,6S,8R,9R,10aR)-6-bromo-2-(3-bromopropa-1,2-dien-1-yl)-5-ethyl-decahydrofuro[3,2-b]oxonine-8,9-diol

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.131961476

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.279265323553478

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.839884760833876

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1646218853999155

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
87.6536

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
laurendecumallene A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.249   0.594   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.733   0.861   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.743   2.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.743   3.581   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.733   4.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.249   5.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.583   4.258   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.110   2.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.583   1.364   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0       5.763   0.374   0.000  0.00  0.00          Br+0
HETATM   11  O   UNK     0       5.763   5.248   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.517   6.545   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.722   4.057   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.627   2.811   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.722   1.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.167   2.811   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.937   1.477   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.707   0.144   0.000  0.00  0.00           C+0
HETATM   19 Br   UNK     0      -3.937  -1.190   0.000  0.00  0.00          Br+0
HETATM   20  C   UNK     0       3.517  -0.923   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.964  -1.449   0.000  0.00  0.00           C+0
CONECT    1    2    9   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    1   10                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    6                                                            
CONECT   13    4   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14    3                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
4:7,6:13-Bisepoxy-9,10-diol-1,12-dibromopentadeca-1,2-diene	MeSH

Chemical Formula

C₁₅H₂₂Br₂O₄

Average Mass

426.1450 Da

Monoisotopic Mass

423.98848 Da

IUPAC Name

(2S,3aR,5R,6S,8R,9R,10aR)-6-bromo-2-(3-bromopropa-1,2-dien-1-yl)-5-ethyl-decahydrofuro[3,2-b]oxonine-8,9-diol

Traditional Name

laurendecumallene A

CAS Registry Number

Not Available

SMILES

CC[C@H]1O[C@@H]2C[C@H](O[C@@H]2C[C@@H](O)[C@H](O)C[C@@H]1Br)C=C=CBr

InChI Identifier

InChI=1S/C15H22Br2O4/c1-2-13-10(17)7-11(18)12(19)8-15-14(21-13)6-9(20-15)4-3-5-16/h4-5,9-15,18-19H,2,6-8H2,1H3/t3?,9-,10+,11-,12-,13-,14-,15-/m1/s1

InChI Key

BYNNASQGMHJTHX-JFPGLQQHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laurencia decumbens	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxolanes

Sub Class

Not Available

Direct Parent

Oxolanes

Alternative Parents

Substituents

Oxolane
1,2-diol
Secondary alcohol
Dialkyl ether
Oxacycle
Vinyl halide
Vinyl bromide
Ether
Organic oxygen compound
Organobromide
Organohalogen compound
Organooxygen compound
Hydrocarbon derivative
Alkyl halide
Alkyl bromide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.38	ALOGPS
logP	2.13	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.65 m³·mol⁻¹	ChemAxon
Polarizability	36.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039605

Chemspider ID

23076549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23643737

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Phan CS, Kamada T, Vairappan CS: Two new epimers of C15-acetogenin, 4-epi-isolaurallene and 4-epi-itomanallene A as diastereomeric model. Nat Prod Res. 2020 Apr;34(7):1008-1013. doi: 10.1080/14786419.2018.1543681. Epub 2019 Jan 2. [PubMed:30600714 ]
Ji NY, Li XM, Li K, Wang BG: Laurendecumallenes A-B and laurendecumenynes A-B, halogenated nonterpenoid C(15)-acetogenins from the marine red alga Laurencia decumbens. J Nat Prod. 2007 Sep;70(9):1499-502. doi: 10.1021/np0701172. Epub 2007 Aug 22. [PubMed:17711344 ]

Showing NP-Card for (+)-Laurendecumallene A (NP0076771)

MOL for NP0076771 ((+)-Laurendecumallene A)

3D MOL for NP0076771 ((+)-Laurendecumallene A)

3D SDF for NP0076771 ((+)-Laurendecumallene A)

3D-SDF for NP0076771 ((+)-Laurendecumallene A)

PDB for NP0076771 ((+)-Laurendecumallene A)

3D PDB for NP0076771 ((+)-Laurendecumallene A)

SMILES for NP0076771 ((+)-Laurendecumallene A)

INCHI for NP0076771 ((+)-Laurendecumallene A)

Structure for NP0076771 ((+)-Laurendecumallene A)

3D Structure for NP0076771 ((+)-Laurendecumallene A)