NP-MRD: Showing NP-Card for (1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid (NP0186303)

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Record Information

Version

2.0

Created at

2022-09-04 02:06:06 UTC

Updated at

2022-09-04 02:06:06 UTC

NP-MRD ID

NP0186303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid

Description

Helminthosporic acid, also known as helminthospate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid was first documented in 2017 (PMID: 29017401). Based on a literature review a small amount of articles have been published on Helminthosporic acid (PMID: 32302133) (PMID: 29907394).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.0063   -1.7553    1.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3110   -0.6669    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5174    0.2627    1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717    0.4833    2.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0225   -0.2342    3.2782 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4518    1.4492    3.0492 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550    0.9980   -0.0567 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9911    0.9615   -1.0726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0773    1.9333   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    1.7411    0.6362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -0.4725   -0.9213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7886   -0.7556   -1.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657   -1.3776   -1.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028   -1.2378   -0.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.2020   -0.6855 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6313    0.5163   -0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335   -0.2466   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8829    0.0737    1.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -2.5880    0.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -1.3697    1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3032   -2.1933    2.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1181    2.3066    3.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335    2.0163    0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    1.1095   -2.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9248    1.9302   -1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202    2.9560   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4752    2.5894    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5782   -0.5888   -0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180   -0.0561   -2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333   -1.8079   -1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107   -1.0725   -2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7477   -2.4162   -1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6769   -1.9032   -1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293   -1.5795    0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013    0.4985   -1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371    1.5841   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9120   -1.2132   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5669    0.3499   -1.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144   -0.3990   -2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628   -0.6353    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9137   -0.3708    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.9783    1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  6
 11  8  1  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  3  1  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  3  2  2  0
  2  1  1  0
  7 15  1  0
  2 11  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 16 36  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 15 35  1  6
 14 33  1  0
 14 34  1  0
 13 31  1  0
 13 32  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
  8 24  1  6
  9 25  1  0
  9 26  1  0
 10 27  1  0
  7 23  1  1
  6 22  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652309042204062D          

 18 19  0  0  1  0            999 V2000
   -0.5726    0.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033   -0.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7267   -1.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4028   -0.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0417    0.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278    1.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5469    1.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0860   -1.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399   -2.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  3  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@]2(C)[C@@H](CO)[C@H]1C(C(O)=O)=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-8(2)10-5-6-15(4)9(3)12(14(17)18)13(10)11(15)7-16/h8,10-11,13,16H,5-7H2,1-4H3,(H,17,18)/t10-,11+,13+,15+/m1/s1

> <INCHI_KEY>
RBCVCNVBAWEHLS-MPXAEWJHSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.58663113985454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,5S,8S)-8-(hydroxymethyl)-1,7-dimethyl-4-(propan-2-yl)bicyclo[3.2.1]oct-6-ene-6-carboxylic acid

> <JCHEM_LOGP>
2.341165953

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.659633326755984

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.889759509082492

> <JCHEM_PKA_STRONGEST_BASIC>
-1.198076776924383

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
70.8724

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,5S,8S)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.069   1.777   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.297   0.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.297  -0.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.126  -1.404   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.356  -2.967   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.619  -0.853   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.501  -1.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.934   0.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.811   1.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.092   2.150   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.501   1.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.021   3.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.003   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.671   0.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.003  -1.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.894  -2.638   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.489  -2.854   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.434  -4.149   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8   15                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8    2   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Helminthospate	Generator
Helminthospic acid	Generator

Chemical Formula

C₁₅H₂₄O₃

Average Mass

252.3540 Da

Monoisotopic Mass

252.17254 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC[C@]2(C)[C@@H](CO)[C@H]1C(C(O)=O)=C2C

InChI Identifier

InChI=1S/C15H24O3/c1-8(2)10-5-6-15(4)9(3)12(14(17)18)13(10)11(15)7-16/h8,10-11,13,16H,5-7H2,1-4H3,(H,17,18)/t10-,11+,13+,15+/m1/s1

InChI Key

RBCVCNVBAWEHLS-MPXAEWJHSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

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

Sesquiterpenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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

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

23148013

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14165721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li YY, Tan XM, Wang YD, Yang J, Zhang YG, Sun BD, Gong T, Guo LP, Ding G: Bioactive seco-Sativene Sesquiterpenoids from an Artemisia desertorum Endophytic Fungus, Cochliobolus sativus. J Nat Prod. 2020 May 22;83(5):1488-1494. doi: 10.1021/acs.jnatprod.9b01148. Epub 2020 Apr 17. [PubMed:32302133 ]
Miyazaki S, Tomita K, Yamane H, Kobayashi M, Asami T, Nakajima M: Characterization of a helminthosporic acid analog that is a selective agonist of gibberellin receptor. Bioorg Med Chem Lett. 2018 Aug 1;28(14):2465-2470. doi: 10.1016/j.bmcl.2018.06.005. Epub 2018 Jun 5. [PubMed:29907394 ]
Miyazaki S, Jiang K, Kobayashi M, Asami T, Nakajima M: Helminthosporic acid functions as an agonist for gibberellin receptor. Biosci Biotechnol Biochem. 2017 Nov;81(11):2152-2159. doi: 10.1080/09168451.2017.1381018. Epub 2017 Oct 11. [PubMed:29017401 ]
LOTUS database [Link]

Showing NP-Card for (1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid (NP0186303)

MOL for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

3D MOL for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

3D SDF for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

3D-SDF for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

PDB for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

3D PDB for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

SMILES for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

INCHI for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

Structure for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)

3D Structure for NP0186303 ((1r,4r,5s,8s)-8-(hydroxymethyl)-4-isopropyl-1,7-dimethylbicyclo[3.2.1]oct-6-ene-6-carboxylic acid)