NP-MRD: Showing NP-Card for leucettamol a (NP0211305)

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Record Information

Version

2.0

Created at

2022-09-05 09:32:25 UTC

Updated at

2022-09-05 09:32:25 UTC

NP-MRD ID

NP0211305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

leucettamol a

Description

Leucettamol a belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Thus, leucettamol a is considered to be a sphingoid base. leucettamol a is found in Leucetta microraphis. leucettamol a was first documented in 2003 (PMID: 12608847). Based on a literature review a significant number of articles have been published on Leucettamol a (PMID: 32296023) (PMID: 28364227) (PMID: 22873794) (PMID: 19159253) (PMID: 19006668).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052211322D          

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    7.9993    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0211305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](N)[C@H](O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C[C@@H](O)[C@H](C)N

> <INCHI_IDENTIFIER>
InChI=1S/C30H52N2O2/c1-27(31)29(33)25-23-21-19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-22-24-26-30(34)28(2)32/h3,5-6,8-9,11-12,14-15,17,21,23,27-30,33-34H,4,7,10,13,16,18-20,22,24-26,31-32H2,1-2H3/b5-3-,8-6-,11-9-,14-12-,17-15-,23-21-/t27-,28-,29+,30+/m0/s1

> <INCHI_KEY>
CXFKWMQQNSTRAS-MVRCMUOWSA-N

> <FORMULA>
C30H52N2O2

> <MOLECULAR_WEIGHT>
472.758

> <EXACT_MASS>
472.402878922

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
58.51055253021269

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,5Z,8Z,11Z,14Z,17Z,20Z,28R,29S)-2,29-diaminotriaconta-5,8,11,14,17,20-hexaene-3,28-diol

> <JCHEM_LOGP>
6.336340591333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.892947833950839

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.288862522572167

> <JCHEM_PKA_STRONGEST_BASIC>
10.128925037543267

> <JCHEM_POLAR_SURFACE_AREA>
92.5

> <JCHEM_REFRACTIVITY>
156.06280000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
leucettamol A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.262  10.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.262   9.391   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.595   8.621   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.072   8.621   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.406   9.391   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.072   7.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.406   6.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.406   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.072   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.072   2.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.262   1.691   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.595   2.461   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.929   1.691   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.929   0.151   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.595  -0.619   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.595  -2.159   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.929  -2.929   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.263  -2.159   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.596  -2.929   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.930  -2.159   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.930  -0.619   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.264   0.151   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.264   1.691   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.930   2.461   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.598   6.311   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      14.932   2.461   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₂N₂O₂

Average Mass

472.7580 Da

Monoisotopic Mass

472.40288 Da

IUPAC Name

(2S,3R,5Z,8Z,11Z,14Z,17Z,20Z,28R,29S)-2,29-diaminotriaconta-5,8,11,14,17,20-hexaene-3,28-diol

Traditional Name

leucettamol A

CAS Registry Number

Not Available

SMILES

C[C@H](N)[C@H](O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C[C@@H](O)[C@H](C)N

InChI Identifier

InChI=1S/C30H52N2O2/c1-27(31)29(33)25-23-21-19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-22-24-26-30(34)28(2)32/h3,5-6,8-9,11-12,14-15,17,21,23,27-30,33-34H,4,7,10,13,16,18-20,22,24-26,31-32H2,1-2H3/b5-3-,8-6-,11-9-,14-12-,17-15-,23-21-/t27-,28-,29+,30+/m0/s1

InChI Key

CXFKWMQQNSTRAS-MVRCMUOWSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Leucetta microraphis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-aminoalcohols

Alternative Parents

Substituents

Secondary alcohol
1,2-aminoalcohol
Organic oxygen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Primary aliphatic amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Sphingoid base analogs (LMSP01080040 )

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	6.34	ChemAxon
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	10.13	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	92.5 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	156.06 m³·mol⁻¹	ChemAxon
Polarizability	58.51 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00044866

Chemspider ID

8160488

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9984898

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Deng L, Meng T, Chen L, Wei W, Wang P: The role of ubiquitination in tumorigenesis and targeted drug discovery. Signal Transduct Target Ther. 2020 Feb 29;5(1):11. doi: 10.1038/s41392-020-0107-0. [PubMed:32296023 ]
Abdjul DB, Yamazaki H, Kanno SI, Tomizawa A, Rotinsulu H, Wewengkang DS, Sumilat DA, Ukai K, Kapojos MM, Namikoshi M: An anti-mycobacterial bisfunctionalized sphingolipid and new bromopyrrole alkaloid from the Indonesian marine sponge Agelas sp. J Nat Med. 2017 Jul;71(3):531-536. doi: 10.1007/s11418-017-1085-6. Epub 2017 Mar 31. [PubMed:28364227 ]
Ushiyama S, Umaoka H, Kato H, Suwa Y, Morioka H, Rotinsulu H, Losung F, Mangindaan RE, de Voogd NJ, Yokosawa H, Tsukamoto S: Manadosterols A and B, sulfonated sterol dimers inhibiting the Ubc13-Uev1A interaction, isolated from the marine sponge Lissodendryx fibrosa. J Nat Prod. 2012 Aug 24;75(8):1495-9. doi: 10.1021/np300352u. Epub 2012 Aug 8. [PubMed:22873794 ]
Dalisay DS, Tsukamoto S, Molinski TF: Absolute configuration of the alpha,omega-bifunctionalized sphingolipid leucettamol A from Leucetta microrhaphis by deconvoluted exciton coupled CD. J Nat Prod. 2009 Mar 27;72(3):353-9. doi: 10.1021/np800549n. [PubMed:19159253 ]
Tsukamoto S, Takeuchi T, Rotinsulu H, Mangindaan RE, van Soest RW, Ukai K, Kobayashi H, Namikoshi M, Ohta T, Yokosawa H: Leucettamol A: a new inhibitor of Ubc13-Uev1A interaction isolated from a marine sponge, Leucetta aff. microrhaphis. Bioorg Med Chem Lett. 2008 Dec 15;18(24):6319-20. doi: 10.1016/j.bmcl.2008.10.110. Epub 2008 Oct 31. [PubMed:19006668 ]
Crews P, Clark DP, Tenney K: Variation in the alkaloids among indo-pacific Leucetta sponges. J Nat Prod. 2003 Feb;66(2):177-82. doi: 10.1021/np020371o. [PubMed:12608847 ]
LOTUS database [Link]

Showing NP-Card for leucettamol a (NP0211305)

MOL for NP0211305 (leucettamol a)

3D MOL for NP0211305 (leucettamol a)

3D SDF for NP0211305 (leucettamol a)

3D-SDF for NP0211305 (leucettamol a)

PDB for NP0211305 (leucettamol a)

3D PDB for NP0211305 (leucettamol a)

SMILES for NP0211305 (leucettamol a)

INCHI for NP0211305 (leucettamol a)

Structure for NP0211305 (leucettamol a)

3D Structure for NP0211305 (leucettamol a)