NP-MRD: Showing NP-Card for Botryaloic acid (NP0064567)

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Record Information

Version

2.0

Created at

2022-04-28 08:46:17 UTC

Updated at

2022-04-28 08:46:17 UTC

NP-MRD ID

NP0064567

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Botryaloic acid

Description

Botryaloic acid, also known as botryaloate, belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Botryaloic acid is found in Botryotinia fuckeliana. Based on a literature review very few articles have been published on Botryaloic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
    3.4628   -1.3763   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0132   -0.9415   -0.6598 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0344    0.3670   -1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.2766   -1.1311 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3971    2.6057   -1.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0935    1.1349    0.0846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3770    1.4703   -0.1020 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8627    2.4316    0.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6364    2.1709   -1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1569    0.2095    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389   -0.9355    0.1767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0289   -1.5715   -1.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7234   -1.9143    1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9831   -3.1113    0.8571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0041   -1.4781    2.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280   -0.2130    0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2614    0.0005    2.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452   -0.8666    0.6763 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3869   -2.1890    1.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689   -3.2568    0.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -2.4357   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001   -1.3750   -1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9272   -0.7170    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6288   -1.7908   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1293    0.1702   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091    0.8833   -1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    1.2522   -2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203    2.8406   -0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    1.8638    0.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6572    1.9948    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396    2.5550    0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330    3.3924    0.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8791    2.9334   -1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8148    1.4685   -2.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104    2.7303   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061    0.0475   -0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8256    0.2112    0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5468   -1.0198   -1.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0822   -1.7768   -1.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6076   -2.6100   -1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -1.2894    2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -0.6714    2.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271   -0.2042    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362   -2.2659    2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 15  1  0
 13 14  2  0
 11 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  2  0
 18  2  1  0
 16  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  4 27  1  6
  5 28  1  0
  6 29  1  1
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  1
 19 44  1  0
M  END


  Mrv1652304282210462D          

 20 21  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314    0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    2.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5314    2.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558    2.5021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    3.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    2.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   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  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  1  0  0  0
  9 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  5 18  1  6  0  0  0
  3 19  1  6  0  0  0
  1 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064567

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](O)[C@H]2C(C)(C)C[C@](C)(C(O)=O)[C@@]2(O)[C@H]1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O5/c1-8-5-10(17)11-13(2,3)7-14(4,12(18)19)15(11,20)9(8)6-16/h6,8-11,17,20H,5,7H2,1-4H3,(H,18,19)/t8-,9+,10+,11+,14-,15-/m1/s1

> <INCHI_KEY>
VBXAFEYVTZXMPM-RCJNEMEQSA-N

> <FORMULA>
C15H24O5

> <MOLECULAR_WEIGHT>
284.352

> <EXACT_MASS>
284.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.537029922756265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3aR,4S,6R,7S,7aS)-7-formyl-4,7a-dihydroxy-1,3,3,6-tetramethyl-octahydro-1H-indene-1-carboxylic acid

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.668664959

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.712601035114066

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.356702318989764

> <JCHEM_PKA_STRONGEST_BASIC>
-2.872662690250003

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
71.9975

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aR,4S,6R,7S,7aS)-7-formyl-4,7a-dihydroxy-1,3,3,6-tetramethyl-hexahydroindene-1-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       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.258   6.693   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.992   0.555   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.430   0.087   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.430   5.598   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.992   5.131   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.478   4.671   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.328   6.634   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.429   5.144   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9   18                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   14   15                                             
CONECT   10    9   11                                                       
CONECT   11   10    4   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    5                                                            
CONECT   19    3                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Botryaloate	Generator

Chemical Formula

C₁₅H₂₄O₅

Average Mass

284.3520 Da

Monoisotopic Mass

284.16237 Da

IUPAC Name

(1S,3aR,4S,6R,7S,7aS)-7-formyl-4,7a-dihydroxy-1,3,3,6-tetramethyl-octahydro-1H-indene-1-carboxylic acid

Traditional Name

(1S,3aR,4S,6R,7S,7aS)-7-formyl-4,7a-dihydroxy-1,3,3,6-tetramethyl-hexahydroindene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@H]2C(C)(C)C[C@](C)(C(O)=O)[C@@]2(O)[C@H]1C=O

InChI Identifier

InChI=1S/C15H24O5/c1-8-5-10(17)11-13(2,3)7-14(4,12(18)19)15(11,20)9(8)6-16/h6,8-11,17,20H,5,7H2,1-4H3,(H,18,19)/t8-,9+,10+,11+,14-,15-/m1/s1

InChI Key

VBXAFEYVTZXMPM-RCJNEMEQSA-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
Botrytis cinerea	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Bicyclic monoterpenoid
11-noriridane monoterpenoid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	0.89	ALOGPS
logP	0.67	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72 m³·mol⁻¹	ChemAxon
Polarizability	29.54 Å³	ChemAxon
Number of Rings	2	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

C00021568

Chemspider ID

78443492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101967066

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Botryaloic acid (NP0064567)

MOL for NP0064567 (Botryaloic acid)

3D MOL for NP0064567 (Botryaloic acid)

3D SDF for NP0064567 (Botryaloic acid)

3D-SDF for NP0064567 (Botryaloic acid)

PDB for NP0064567 (Botryaloic acid)

3D PDB for NP0064567 (Botryaloic acid)

SMILES for NP0064567 (Botryaloic acid)

INCHI for NP0064567 (Botryaloic acid)

Structure for NP0064567 (Botryaloic acid)

3D Structure for NP0064567 (Botryaloic acid)