NP-MRD: Showing NP-Card for Bostrychine H (NP0332198)

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Record Information

Version

2.0

Created at

2023-12-07 04:00:52 UTC

Updated at

2024-09-03 04:18:22 UTC

NP-MRD ID

NP0332198

Natural Product DOI

https://doi.org/10.57994/1371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bostrychine H

Description

Bostrychine H belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Bostrychine H was first documented in 2023 (PMID: 37888478). Based on a literature review very few articles have been published on Bostrychine H.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 12072304002D          

 26 26  0  0  1  0            999 V2000
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6131   -2.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862   -2.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   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  2  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
  9 11  2  0  0  0  0
  4 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  1  0  0  0
M  END


  Mrv2104 12072304002D          

 26 26  0  0  1  0            999 V2000
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6131   -2.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862   -2.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   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  2  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
  9 11  2  0  0  0  0
  4 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0332198

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@](O)(CO)C\C1=N/[C@@H]([C@H](C)O)C(O)=O)NCCCC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H27N3O7/c1-9(21)13(15(23)24)19-11-7-16(25,8-20)6-10(14(11)26-2)18-5-3-4-12(17)22/h9,13,18,20-21,25H,3-8H2,1-2H3,(H2,17,22)(H,23,24)/b19-11+/t9-,13-,16+/m0/s1

> <INCHI_KEY>
OHLRKWUXNDOHJH-JLYSHPRASA-N

> <FORMULA>
C16H27N3O7

> <MOLECULAR_WEIGHT>
373.406

> <EXACT_MASS>
373.184900221

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.23672662065395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-{[(1E,5R)-3-[(3-carbamoylpropyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxybutanoic acid

> <JCHEM_LOGP>
-3.8088937296845153

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.619269702774206

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1976498819834482

> <JCHEM_PKA_STRONGEST_BASIC>
4.27189886412501

> <JCHEM_POLAR_SURFACE_AREA>
174.7

> <JCHEM_REFRACTIVITY>
93.0475

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-{[(1E,5R)-3-[(3-carbamoylpropyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-DEC-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-DEC-23         0                                  
HETATM    1  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.335  -1.540   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.011  -5.030   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.991  -5.030   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.508  -4.762   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -6.668  -0.770   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -10.669  -1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -9.336   0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17    3   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₇N₃O₇

Average Mass

373.4060 Da

Monoisotopic Mass

373.18490 Da

IUPAC Name

(2S,3S)-2-{[(1E,5R)-3-[(3-carbamoylpropyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxybutanoic acid

Traditional Name

(2S,3S)-2-{[(1E,5R)-3-[(3-carbamoylpropyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxybutanoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@](O)(CO)C\C1=N/[C@@H]([C@H](C)O)C(O)=O)NCCCC(N)=O

InChI Identifier

InChI=1S/C16H27N3O7/c1-9(21)13(15(23)24)19-11-7-16(25,8-20)6-10(14(11)26-2)18-5-3-4-12(17)22/h9,13,18,20-21,25H,3-8H2,1-2H3,(H2,17,22)(H,23,24)/b19-11+/t9-,13-,16+/m0/s1

InChI Key

OHLRKWUXNDOHJH-JLYSHPRASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, D2O, experimental)	orfmaria@gmail.com	University of Innsbruck	Maria Orfanoudaki	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, D2O, experimental)	orfmaria@gmail.com	University of Innsbruck	Maria Orfanoudaki	2024-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, D2O, experimental)	orfmaria@gmail.com	University of Innsbruck	Maria Orfanoudaki	2024-05-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D2O, experimental)	orfmaria@gmail.com	University of Innsbruck	Maria Orfanoudaki	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D2O, experimental)	orfmaria@gmail.com	University of Innsbruck	Maria Orfanoudaki	2024-05-09	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bostrychia scorpioides		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Short-chain hydroxy acid
Hydroxy fatty acid
Branched fatty acid
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Fatty amide
Tertiary alcohol
Secondary ketimine
Azomethine
Amino acid
Secondary alcohol
Ketimine
Carboxamide group
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Amine
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-3.8	ChemAxon
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	4.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	174.7 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	93.05 m³·mol⁻¹	ChemAxon
Polarizability	38.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Orfanoudaki M, Alilou M, Hartmann A, Mayr J, Karsten U, Nguyen-Ngoc H, Ganzera M: Isolation and Structure Elucidation of Novel Mycosporine-like Amino Acids from the Two Intertidal Red Macroalgae Bostrychia scorpioides and Catenella caespitosa. Mar Drugs. 2023 Oct 18;21(10):543. doi: 10.3390/md21100543. [PubMed:37888478 ]
DOI: 10.3390/md21100543

Showing NP-Card for Bostrychine H (NP0332198)

MOL for NP0332198 (Bostrychine H)

3D MOL for NP0332198 (Bostrychine H)

3D SDF for NP0332198 (Bostrychine H)

3D-SDF for NP0332198 (Bostrychine H)

PDB for NP0332198 (Bostrychine H)

3D PDB for NP0332198 (Bostrychine H)

SMILES for NP0332198 (Bostrychine H)

INCHI for NP0332198 (Bostrychine H)

Structure for NP0332198 (Bostrychine H)

3D Structure for NP0332198 (Bostrychine H)