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Showing NP-Card for (-)-Sinuolatin A (NP0081901)

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Record Information
Version2.0
Created at2022-04-29 02:58:14 UTC
Updated at2022-04-29 02:58:14 UTC
NP-MRD IDNP0081901
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Sinuolatin A
Description(1R,2R,3R,5S,6S,8S,9S,10S,11R,15S)-3,9,10,15-tetrahydroxy-6-(methoxymethyl)-12,12-dimethyl-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-7-one belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (-)-Sinuolatin A is found in Isodon sinuolata. Based on a literature review very few articles have been published on (1R,2R,3R,5S,6S,8S,9S,10S,11R,15S)-3,9,10,15-tetrahydroxy-6-(methoxymethyl)-12,12-dimethyl-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-7-one.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0081901 ((-)-Sinuolatin A)


  Mrv1652304292204582D          

 28 32  0  0  1  0            999 V2000
    5.9654    0.8733    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2914    1.4028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6130    2.2780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4534    2.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0347    1.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7851    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2979    3.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0339    3.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0870    3.0518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2016    2.7997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8347    1.9607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3822    1.1787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9450    0.4301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1010    0.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5394    0.9327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3291    1.7609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0131    2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978    3.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    2.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038    2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6269    3.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484    1.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4151   -0.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9045    2.4746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072    1.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6588    3.4210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685    3.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7835    0.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  6  0  0  0
 11 22  1  6  0  0  0
 13 23  1  6  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  1  0  0  0
 10 26  1  6  0  0  0
  9 27  1  1  0  0  0
  1 28  1  6  0  0  0
M  END
Download

3D MOL for NP0081901 ((-)-Sinuolatin A)

Download
3D SDF for NP0081901 ((-)-Sinuolatin A)

  Mrv1652304292204582D          

 28 32  0  0  1  0            999 V2000
    5.9654    0.8733    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2914    1.4028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6130    2.2780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4534    2.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0347    1.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7851    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2979    3.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0339    3.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0870    3.0518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2016    2.7997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8347    1.9607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3822    1.1787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9450    0.4301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1010    0.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5394    0.9327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3291    1.7609    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0131    2.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978    3.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    2.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038    2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6269    3.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484    1.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4151   -0.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9045    2.4746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072    1.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6588    3.4210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685    3.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7835    0.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 22  1  6  0  0  0
 11 22  1  6  0  0  0
 13 23  1  6  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  1  0  0  0
 10 26  1  6  0  0  0
  9 27  1  1  0  0  0
  1 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@@H]1[C@H]2C[C@]3([C@H]([C@H](O)C2)[C@]24CO[C@]3(O)[C@@H](O)[C@@H]2C(C)(C)CC[C@@H]4O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O7/c1-18(2)5-4-13(23)19-9-28-21(26,17(25)15(18)19)20-7-10(6-12(22)14(19)20)11(8-27-3)16(20)24/h10-15,17,22-23,25-26H,4-9H2,1-3H3/t10-,11-,12-,13+,14-,15-,17+,19-,20+,21-/m1/s1

> <INCHI_KEY>
JXNJRPBFAVZWNL-IAXYKNGSSA-N

> <FORMULA>
C21H32O7

> <MOLECULAR_WEIGHT>
396.48

> <EXACT_MASS>
396.21480337

$$$$

Download
3D-SDF for NP0081901 ((-)-Sinuolatin A)
Download
PDB for NP0081901 ((-)-Sinuolatin A)
HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      11.135   1.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.877   2.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.478   4.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.046   4.590   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.131   3.466   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.666   1.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.756   6.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.130   5.685   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.496   5.697   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.843   5.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.158   3.660   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.180   2.200   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.364   0.803   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.788   0.532   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.740   1.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.348   3.287   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.624   4.230   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.409   5.755   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.897   3.805   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.621   5.320   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.170   5.838   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.064   2.525   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.241  -0.463   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.155   4.619   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.600   3.324   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.830   6.386   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.021   7.144   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.796   0.128   0.000  0.00  0.00           O+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3   12   25                                             
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7    8                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    3   10   27                                                  
CONECT   10    9   11   24   26                                             
CONECT   11   10   12   17   22                                             
CONECT   12   11    2   13                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   15   11                                                       
CONECT   23   13                                                            
CONECT   24   10   25                                                       
CONECT   25   24    2                                                       
CONECT   26   10                                                            
CONECT   27    9                                                            
CONECT   28    1                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

Download
3D PDB for NP0081901 ((-)-Sinuolatin A)
Download
SMILES for NP0081901 ((-)-Sinuolatin A)
COC[C@@H]1[C@H]2C[C@]3([C@H]([C@H](O)C2)[C@]24CO[C@]3(O)[C@@H](O)[C@@H]2C(C)(C)CC[C@@H]4O)C1=O
Download
INCHI for NP0081901 ((-)-Sinuolatin A)
InChI=1S/C21H32O7/c1-18(2)5-4-13(23)19-9-28-21(26,17(25)15(18)19)20-7-10(6-12(22)14(19)20)11(8-27-3)16(20)24/h10-15,17,22-23,25-26H,4-9H2,1-3H3/t10-,11-,12-,13+,14-,15-,17+,19-,20+,21-/m1/s1
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC21H32O7
Average Mass396.4800 Da
Monoisotopic Mass396.21480 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
COC[C@@H]1[C@H]2C[C@]3([C@H]([C@H](O)C2)[C@]24CO[C@]3(O)[C@@H](O)[C@@H]2C(C)(C)CC[C@@H]4O)C1=O
InChI Identifier
InChI=1S/C21H32O7/c1-18(2)5-4-13(23)19-9-28-21(26,17(25)15(18)19)20-7-10(6-12(22)14(19)20)11(8-27-3)16(20)24/h10-15,17,22-23,25-26H,4-9H2,1-3H3/t10-,11-,12-,13+,14-,15-,17+,19-,20+,21-/m1/s1
InChI KeyJXNJRPBFAVZWNL-IAXYKNGSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Isodon sinuolataPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentKaurane diterpenoids  
Alternative Parents
Substituents
  • Kaurane diterpenoid
    • 

  • Oxane
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162888604  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available