NP-MRD: Showing NP-Card for Abundisporin H (NP0331916)

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Record Information

Version

2.0

Created at

2023-10-05 12:05:06 UTC

Updated at

2024-09-03 04:17:25 UTC

NP-MRD ID

NP0331916

Natural Product DOI

https://doi.org/10.57994/1028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Abundisporin H

Description

Abundisporin H belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on Abundisporin H.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10052312052D          

 21 23  0  0  1  0            999 V2000
    1.7756   -2.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1656   -1.9612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5556   -1.2342    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1210   -0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -0.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9064   -1.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052   -1.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446   -2.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410   -1.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084   -2.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0050   -3.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8618    0.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9902   -1.9354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3802   -1.2084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2116   -0.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1462   -0.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2641   -0.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7945   -1.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148   -1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4248   -2.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6002   -2.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  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
  6  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 12  2  0  0  0  0
  3 13  1  6  0  0  0
  3 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(=O)C3=C(C(=O)OC3)[C@]1(C)CCC[C@]2(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-14-4-3-5-15(2,13(18)19)10(14)6-9(16)8-7-20-12(17)11(8)14/h10H,3-7H2,1-2H3,(H,18,19)/t10-,14-,15+/m1/s1

> <INCHI_KEY>
FVJBARSRVBARNU-KMUNFCNLSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.922394977826777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5aR,6S,9aR)-6,9a-dimethyl-1,4-dioxo-1H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-naphtho[1,2-c]furan-6-carboxylic acid

> <JCHEM_LOGP>
2.011910971

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.555523296748281

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.122249602410473

> <JCHEM_PKA_STRONGEST_BASIC>
-6.922633258754713

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
69.69250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,6S,9aR)-6,9a-dimethyl-1,4-dioxo-3H,5H,5aH,7H,8H,9H-naphtho[1,2-c]furan-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-23         0                                  
HETATM    1  C   UNK     0       3.314  -5.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.042  -3.661   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.770  -2.304   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.959  -0.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.420  -1.043   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.692  -2.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.196  -2.767   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.083  -4.303   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.503  -3.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.509  -4.885   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.876  -6.381   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.609   0.266   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       5.582  -3.613   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       6.310  -2.256   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.995  -0.748   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.740  -1.684   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.960  -0.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.950  -2.637   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.121  -3.565   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.393  -4.922   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.854  -4.970   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   21                                             
CONECT    3    2    4   13   14                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9    6    2   10                                                  
CONECT   10    9    8   11                                                  
CONECT   11   10                                                            
CONECT   12    5                                                            
CONECT   13    3                                                            
CONECT   14    3   15   16   19                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₅

Average Mass

278.3040 Da

Monoisotopic Mass

278.11542 Da

IUPAC Name

(5aR,6S,9aR)-6,9a-dimethyl-1,4-dioxo-1H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-naphtho[1,2-c]furan-6-carboxylic acid

Traditional Name

(5aR,6S,9aR)-6,9a-dimethyl-1,4-dioxo-3H,5H,5aH,7H,8H,9H-naphtho[1,2-c]furan-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(=O)C3=C(C(=O)OC3)[C@]1(C)CCC[C@]2(C)C(O)=O

InChI Identifier

InChI=1S/C15H18O5/c1-14-4-3-5-15(2,13(18)19)10(14)6-9(16)8-7-20-12(17)11(8)14/h10H,3-7H2,1-2H3,(H,18,19)/t10-,14-,15+/m1/s1

InChI Key

FVJBARSRVBARNU-KMUNFCNLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
FAILED_TO_DETECT NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, CD3OD, experimental)	sherif_elsayed@pharma.asu.edu.eg	Not Available	Not Available	2023-10-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD3OD, experimental)	sherif_elsayed@pharma.asu.edu.eg	Not Available	Not Available	2023-10-05	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
Cyclohexenone
Methyl-branched fatty acid
Heterocyclic fatty acid
Fatty acid ester
Branched fatty acid
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Dihydrofuran
Acryloyl-group
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.01	ChemAxon
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.69 m³·mol⁻¹	ChemAxon
Polarizability	27.92 Å³	ChemAxon
Number of Rings	3	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

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

Showing NP-Card for Abundisporin H (NP0331916)

MOL for NP0331916 (Abundisporin H)

3D MOL for NP0331916 (Abundisporin H)

3D SDF for NP0331916 (Abundisporin H)

3D-SDF for NP0331916 (Abundisporin H)

PDB for NP0331916 (Abundisporin H)

3D PDB for NP0331916 (Abundisporin H)

SMILES for NP0331916 (Abundisporin H)

INCHI for NP0331916 (Abundisporin H)

Structure for NP0331916 (Abundisporin H)

3D Structure for NP0331916 (Abundisporin H)