NP-MRD: Showing NP-Card for goondolinone B (NP0333681)

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Record Information

Version

2.0

Created at

2024-08-01 00:02:38 UTC

Updated at

2026-02-05 17:11:05 UTC

NP-MRD ID

NP0333681

Natural Product DOI

https://doi.org/10.57994/3160

Secondary Accession Numbers

None

Natural Product Identification

Common Name

goondolinone B

Description

Craterone B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. goondolinone B was first documented in 2024 (PMID: 39582162). Based on a literature review very few articles have been published on craterone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04152302362D          

 26 28  0  0  1  0            999 V2000
    0.8043   -0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.2038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8043   -0.3873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9879   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    0.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043    1.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173    1.2534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    2.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082    2.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312    3.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862    3.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182    3.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    2.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    2.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    2.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  2  6  1  1  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  9 13  1  0  0  0  0
  2 14  1  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
  5 17  1  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  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv2104 04152302362D          

 26 28  0  0  1  0            999 V2000
    0.8043   -0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.2038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8043   -0.3873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9879   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    0.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043    1.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173    1.2534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    2.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082    2.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312    3.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862    3.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182    3.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    2.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    2.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    2.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  2  6  1  1  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  9 13  1  0  0  0  0
  2 14  1  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
  5 17  1  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  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC[C@]1(C)OCC2=C(C[C@H]1O)NC1=CC=CC=C1C2=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO5/c1-12(19(24)25)6-5-9-20(2)17(22)10-16-14(11-26-20)18(23)13-7-3-4-8-15(13)21-16/h3-4,7-8,12,17,22H,5-6,9-11H2,1-2H3,(H,21,23)(H,24,25)/t12?,17-,20+/m1/s1

> <INCHI_KEY>
MPVSHMNCZITDMY-CXWYOBRSSA-N

> <FORMULA>
C20H25NO5

> <MOLECULAR_WEIGHT>
359.422

> <EXACT_MASS>
359.173272909

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.021376559886946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3S,4R)-4-hydroxy-3-methyl-11-oxo-1H,3H,4H,5H,6H,11H-oxepino[4,3-b]quinolin-3-yl]-2-methylpentanoic acid

> <JCHEM_LOGP>
2.5873249939999985

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.659756701527819

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.446619238614005

> <JCHEM_PKA_STRONGEST_BASIC>
-2.933748128172266

> <JCHEM_POLAR_SURFACE_AREA>
95.86000000000001

> <JCHEM_REFRACTIVITY>
99.455

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(3S,4R)-4-hydroxy-3-methyl-11-oxo-1H,4H,5H,6H-oxepino[4,3-b]quinolin-3-yl]-2-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-23         0                                  
HETATM    1  C   UNK     0       1.501  -0.723   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -0.380   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.501  -0.723   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.844  -2.224   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.705   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000  -1.920   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.690   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.920   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.690   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -1.920   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.690   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -0.380   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -4.230   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.668   1.007   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.000   2.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.501   2.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.705   1.777   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -4.139   2.340   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.368   3.863   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.802   4.425   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.032   5.948   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.828   6.908   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.394   6.346   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.164   4.823   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.731   4.260   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.527   5.220   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6   14                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3   17                                                       
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   16   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₅NO₅

Average Mass

359.4220 Da

Monoisotopic Mass

359.17327 Da

IUPAC Name

5-[(3S,4R)-4-hydroxy-3-methyl-11-oxo-1H,3H,4H,5H,6H,11H-oxepino[4,3-b]quinolin-3-yl]-2-methylpentanoic acid

Traditional Name

5-[(3S,4R)-4-hydroxy-3-methyl-11-oxo-1H,4H,5H,6H-oxepino[4,3-b]quinolin-3-yl]-2-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC[C@]1(C)OCC2=C(C[C@H]1O)NC1=CC=CC=C1C2=O)C(O)=O

InChI Identifier

InChI=1S/C20H25NO5/c1-12(19(24)25)6-5-9-20(2)17(22)10-16-14(11-26-20)18(23)13-7-3-4-8-15(13)21-16/h3-4,7-8,12,17,22H,5-6,9-11H2,1-2H3,(H,21,23)(H,24,25)/t12?,17-,20+/m1/s1

InChI Key

MPVSHMNCZITDMY-CXWYOBRSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	The University of Queensland	Jianying Han	2024-08-01	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
Actinomadura		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Dihydroquinolone
Quinoline
Dihydroquinoline
Polyhalopyridine
2-halopyridine
Methylpyridine
Hydroxypyridine
Methyl-branched fatty acid
Tetrahydropyridine
Short-chain hydroxy acid
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Amino acid
Secondary alcohol
Ketone
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Ether
Secondary aliphatic amine
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.59	ChemAxon
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.46 m³·mol⁻¹	ChemAxon
Polarizability	39.02 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

Han J, Bruhn DF, Roberts DC, Burkman EJ, Moreno Y, Bernhardt PV, Salim AA, Capon RJ: Goondolinones A and B: Terpenyl-quinolin-4(1H)-ones from an Australian Volcanic Crater Soil-Derived Actinomadura sp., with Selective Activity against Dirofilaria immitis (Heartworm). J Nat Prod. 2024 Dec 27;87(12):2855-2862. doi: 10.1021/acs.jnatprod.4c01146. Epub 2024 Nov 24. [PubMed:39582162 ]
DOI: 10.1021/acs.jnatprod.4c01146
PMID: 39582162

Showing NP-Card for goondolinone B (NP0333681)

MOL for NP0333681 (goondolinone B)

3D MOL for NP0333681 (goondolinone B)

3D SDF for NP0333681 (goondolinone B)

3D-SDF for NP0333681 (goondolinone B)

PDB for NP0333681 (goondolinone B)

3D PDB for NP0333681 (goondolinone B)

SMILES for NP0333681 (goondolinone B)

INCHI for NP0333681 (goondolinone B)

Structure for NP0333681 (goondolinone B)

3D Structure for NP0333681 (goondolinone B)