NP-MRD: Showing NP-Card for 7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid (NP0176285)

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Record Information

Version

2.0

Created at

2022-09-03 13:55:22 UTC

Updated at

2022-09-03 13:55:22 UTC

NP-MRD ID

NP0176285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid

Description

Marinoic acid, also known as marinoate, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid is found in Rhinella marina. 7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid was first documented in 2020 (PMID: 32549266). Based on a literature review very few articles have been published on Marinoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032215552D          

 31 35  0  0  0  0            999 V2000
    4.9880    2.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    1.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7785    2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5690    2.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7599    1.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5504    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1602    0.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697    1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7700    0.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795    0.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7887    1.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    2.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348    2.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    3.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    2.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    2.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9124    1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942    1.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407    1.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9298    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    1.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    1.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6919    2.3331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    2.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284    3.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561    2.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3403    2.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497    3.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668    3.3226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    3.8585    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  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
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  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  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  2  0  0  0  0
 19 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END


  Mrv1652309032215552D          

 31 35  0  0  0  0            999 V2000
    4.9880    2.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    1.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7785    2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5690    2.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7599    1.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5504    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1602    0.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697    1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7700    0.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9795    0.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7887    1.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    2.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348    2.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    3.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    2.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    2.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9124    1.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942    1.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407    1.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9298    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    1.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    1.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6919    2.3331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    2.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284    3.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561    2.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3403    2.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464    3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6497    3.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668    3.3226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    3.8585    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  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
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  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  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  2  0  0  0  0
 19 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176285

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C(CCC11OC(=O)C2C1CCC1CC(O)CCC21C)C1=CC(=O)OC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O7/c1-22-8-5-15(25)12-14(22)3-4-17-19(22)20(27)31-24(17)9-6-16(23(24,2)21(28)29)13-7-10-30-18(26)11-13/h7,10-11,14-17,19,25H,3-6,8-9,12H2,1-2H3,(H,28,29)

> <INCHI_KEY>
PIHCEVPSPPWILX-UHFFFAOYSA-N

> <FORMULA>
C24H30O7

> <MOLECULAR_WEIGHT>
430.497

> <EXACT_MASS>
430.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.96579432759405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxo-2H-pyran-4-yl)-decahydro-1'H-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.532376547

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.131439751309742

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.129757799239475

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569624705851346

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
110.20719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'aH-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       9.311   5.201   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.667   3.702   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.787   4.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.262   4.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.618   2.821   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.094   2.381   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.499   1.764   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.023   2.204   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.904   1.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.428   1.587   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.072   3.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.192   4.143   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.532   5.534   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.269   6.886   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.004   5.337   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.720   3.823   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.436   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.909   2.112   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.249   3.503   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.736   3.787   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.733   2.618   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.781   2.902   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.292   4.355   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.289   5.524   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.800   6.977   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.225   5.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.369   4.561   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.447   5.794   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.946   5.989   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.471   6.202   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.999   7.203   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   11   17   27                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20                                                       
CONECT   27   19   16   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Marinoate	Generator
3beta-Hydroxy-11,12-seco-5beta,14beta-bufa-20,22-dienolide-11,14-olide-12-Oic acid	MeSH

Chemical Formula

C₂₄H₃₀O₇

Average Mass

430.4970 Da

Monoisotopic Mass

430.19915 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C(CCC11OC(=O)C2C1CCC1CC(O)CCC21C)C1=CC(=O)OC=C1)C(O)=O

InChI Identifier

InChI=1S/C24H30O7/c1-22-8-5-15(25)12-14(22)3-4-17-19(22)20(27)31-24(17)9-6-16(23(24,2)21(28)29)13-7-10-30-18(26)11-13/h7,10-11,14-17,19,25H,3-6,8-9,12H2,1-2H3,(H,28,29)

InChI Key

PIHCEVPSPPWILX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhinella marina	LOTUS Database	35616633

Chemical Taxonomy

Description

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
Naphthofuran
Monoterpenoid
Aromatic monoterpenoid
Pyranone
Pyran
Gamma butyrolactone
Dicarboxylic acid or derivatives
Heteroaromatic compound
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

155043

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

178102

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Oliveira RS, Borges BT, Leal AP, Lailowski MM, Bordon KCF, Souza VQ, Vinade L, Santos TGD, Hyslop S, Moura S, Arantes EC, Corrado AP, Dal Belo CA: Chemical and Pharmacological Screening of Rhinella icterica (Spix 1824) Toad Parotoid Secretion in Avian Preparations. Toxins (Basel). 2020 Jun 15;12(6). pii: toxins12060396. doi: 10.3390/toxins12060396. [PubMed:32549266 ]
LOTUS database [Link]

Showing NP-Card for 7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid (NP0176285)

MOL for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

3D MOL for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

3D SDF for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

3D-SDF for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

PDB for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

3D PDB for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

SMILES for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

INCHI for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

Structure for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)

3D Structure for NP0176285 (7'-hydroxy-2,9'a-dimethyl-1'-oxo-3-(2-oxopyran-4-yl)-octahydro-3'ah-spiro[cyclopentane-1,3'-naphtho[1,2-c]furan]-2-carboxylic acid)