NP-MRD: Showing NP-Card for Allogibberic acid (NP0051989)

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Record Information

Version

2.0

Created at

2022-04-27 23:11:20 UTC

Updated at

2022-04-27 23:11:20 UTC

NP-MRD ID

NP0051989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Allogibberic acid

Description

Allogibberic acid, also known as allogibberate, belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. Allogibberic acid is found in Lemna perpusilla strain 6746. Based on a literature review very few articles have been published on Allogibberic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
   -3.5972   -0.0769    1.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6191   -0.0528    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761    0.2211    0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5639    0.3386   -0.4655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7420    0.7234   -1.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612   -0.3053   -0.7705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0216   -0.0777   -1.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3370   -1.7128   -1.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665   -2.0509   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0475   -0.9526   -1.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3268   -1.0171   -0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2188   -2.0499   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -1.8205    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171   -0.5180    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0513    0.5556    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5910    1.9111    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550    0.2707   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6295    1.2430   -0.5485 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5746    2.0870    0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    1.8345    1.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754    3.2056    0.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6312   -0.2878    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018    0.1216    2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -0.5375    1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    1.1796    1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676    1.7080   -1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881    0.5996   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4617   -0.9193   -1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3923   -1.8520   -2.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0611   -2.3883   -0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6346   -2.9864   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9516   -2.2609    0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -0.8909   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9582   -3.0908   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2618   -2.5951    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -0.3001    0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033    2.1000    1.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5704    1.9638   -0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9991    2.7297   -0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194    1.8235   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950    4.1273    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 18  4  1  0
  4  3  1  1
  3  2  1  0
  2  1  2  3
  2  6  1  0
  6  7  1  6
  6  5  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 11 17  1  0
  5  4  1  0
 10  4  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  6
 21 41  1  0
  3 24  1  0
  3 25  1  0
  1 22  1  0
  1 23  1  0
  7 28  1  0
  5 26  1  0
  5 27  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  6
 12 34  1  0
 13 35  1  0
 14 36  1  0
M  END


  Mrv1652304282201112D          

 21 24  0  0  1  0            999 V2000
    3.3060    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3601    0.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6741    0.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9342    0.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801    1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660    1.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    1.4630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5753    0.7329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1577    0.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9732   -0.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5773   -1.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846   -0.9322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.5339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1721    2.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6898    2.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3977    1.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    0.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6489    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1471    0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 14 17  1  1  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@H](C(O)=O)[C@@]34CC(=C)[C@@](O)(C3)CC[C@@H]4C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O3/c1-10-4-3-5-12-13-6-7-18(21)9-17(13,8-11(18)2)15(14(10)12)16(19)20/h3-5,13,15,21H,2,6-9H2,1H3,(H,19,20)/t13-,15-,17+,18+/m1/s1

> <INCHI_KEY>
IFYWTLQMNWNCFH-WCZJQEMASA-N

> <FORMULA>
C18H20O3

> <MOLECULAR_WEIGHT>
284.355

> <EXACT_MASS>
284.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.097828190512132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,9S,12S)-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-2-carboxylic acid

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
2.6199607136666674

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.204828026657186

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.444215457810781

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1473034903855996

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
79.793

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,9S,12S)-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.171   2.478   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.272   0.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.992   0.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.610   0.766   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.510   2.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.790   3.159   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.990   2.731   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.074   1.368   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.161   0.213   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.817  -1.288   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.944  -2.337   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.345  -1.740   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.033   2.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.204   2.863   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.321   4.227   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.288   4.196   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.609   3.494   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.636   1.296   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.078   0.755   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.275   0.397   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.093  -1.451   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   16                                                  
CONECT    8    7    9   13   20                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   17   18                                             
CONECT   15   14   16                                                       
CONECT   16   15    7                                                       
CONECT   17   14                                                            
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8                                                       
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
Allogibberate	Generator
(4Balpha,10beta)-7-hydroxy-1-methyl-8-methylenegibba-1,3,4a(10a)-triene-10-carboxylic acid	MeSH

Chemical Formula

C₁₈H₂₀O₃

Average Mass

284.3550 Da

Monoisotopic Mass

284.14124 Da

IUPAC Name

(1S,2R,9S,12S)-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-2-carboxylic acid

Traditional Name

(1S,2R,9S,12S)-12-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadeca-3,5,7-triene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=C2[C@H](C(O)=O)[C@@]34CC(=C)[C@@](O)(C3)CC[C@@H]4C2=CC=C1

InChI Identifier

InChI=1S/C18H20O3/c1-10-4-3-5-12-13-6-7-18(21)9-17(13,8-11(18)2)15(14(10)12)16(19)20/h3-5,13,15,21H,2,6-9H2,1H3,(H,19,20)/t13-,15-,17+,18+/m1/s1

InChI Key

IFYWTLQMNWNCFH-WCZJQEMASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Lemna perpusilla strain 6746	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Fluorenes

Sub Class

Not Available

Direct Parent

Fluorenes

Alternative Parents

Substituents

Fluorene
Indane
Tertiary alcohol
Cyclic alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

fluorenes (CHEBI:2598 )

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	2.42	ALOGPS
logP	2.62	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.79 m³·mol⁻¹	ChemAxon
Polarizability	31.1 Å³	ChemAxon
Number of Rings	4	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

C00003402

Chemspider ID

390560

KEGG Compound ID

C09061

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442001

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Allogibberic acid (NP0051989)

MOL for NP0051989 (Allogibberic acid)

3D MOL for NP0051989 (Allogibberic acid)

3D SDF for NP0051989 (Allogibberic acid)

3D-SDF for NP0051989 (Allogibberic acid)

PDB for NP0051989 (Allogibberic acid)

3D PDB for NP0051989 (Allogibberic acid)

SMILES for NP0051989 (Allogibberic acid)

INCHI for NP0051989 (Allogibberic acid)

Structure for NP0051989 (Allogibberic acid)

3D Structure for NP0051989 (Allogibberic acid)