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Showing NP-Card for Hetidine (NP0067199)

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Record Information
Version2.0
Created at2022-04-28 11:33:44 UTC
Updated at2022-04-28 11:33:44 UTC
NP-MRD IDNP0067199
Secondary Accession NumbersNone
Natural Product Identification
Common NameHetidine
Description(1R,3R,4S,5S,8R,9S,11S,14S,17S,18R)-3,4-dihydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecane-10,16-dione belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. Hetidine is found in Aconitum heterophyllum, Aconitum heterophyllum Wall. and Delphinium albiflorum. Based on a literature review very few articles have been published on (1R,3R,4S,5S,8R,9S,11S,14S,17S,18R)-3,4-dihydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecane-10,16-dione.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0067199 (Hetidine)


  Mrv1652304282213332D          

 26 31  0  0  1  0            999 V2000
    1.3988    0.1337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8734    0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4829    1.5615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977    0.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    0.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7378   -0.7925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9555   -0.4400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9903   -1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638   -1.7704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5851   -1.1291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6216   -0.1864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2523   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -1.2477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -0.9634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6824   -0.1724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7431   -0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4349    0.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -1.1713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3275   -1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5186   -0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3428   -0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0116   -2.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    0.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787   -1.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -2.5837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 18 16  1  1  0  0  0
 18 19  1  0  0  0  0
  6 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
 13 23  1  0  0  0  0
 11 24  1  1  0  0  0
 10 25  1  1  0  0  0
  9 26  1  1  0  0  0
M  END
Download

3D MOL for NP0067199 (Hetidine)

Download
3D SDF for NP0067199 (Hetidine)

  Mrv1652304282213332D          

 26 31  0  0  1  0            999 V2000
    1.3988    0.1337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8734    0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4829    1.5615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977    0.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    0.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7378   -0.7925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9555   -0.4400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9903   -1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2638   -1.7704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5851   -1.1291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6216   -0.1864    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2523   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -1.2477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -0.9634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6824   -0.1724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7431   -0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4349    0.0821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -1.1713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3275   -1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5186   -0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3428   -0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0116   -2.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8513    0.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787   -1.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -2.5837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 18 16  1  1  0  0  0
 18 19  1  0  0  0  0
  6 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
 13 23  1  0  0  0  0
 11 24  1  1  0  0  0
 10 25  1  1  0  0  0
  9 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@@]2(C)[C@H](O)[C@H](O)C[C@@]34[C@H]1[C@H]1C(=O)[C@H]5C[C@@H]3[C@]1(CC5=C)CC(=O)[C@H]24

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO4/c1-9-5-20-6-11(23)16-19(2)8-22(3)17-14(20)15(25)10(9)4-13(20)21(16,17)7-12(24)18(19)26/h10,12-14,16-18,24,26H,1,4-8H2,2-3H3/t10-,12+,13+,14+,16+,17+,18+,19+,20-,21+/m0/s1

> <INCHI_KEY>
LHSMCOYXDSMPQS-ACBREKFMSA-N

> <FORMULA>
C21H27NO4

> <MOLECULAR_WEIGHT>
357.45

> <EXACT_MASS>
357.194008353

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,4S,5S,8R,9S,11S,14S,17S,18R)-3,4-dihydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-10,16-dione

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
-0.02973704533333349

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.10484468644895

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.577589713318975

> <JCHEM_PKA_STRONGEST_BASIC>
8.226273455186883

> <JCHEM_POLAR_SURFACE_AREA>
77.84

> <JCHEM_REFRACTIVITY>
94.63100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4S,5S,8R,9S,11S,14S,17S,18R)-3,4-dihydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-10,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0067199 (Hetidine)
Download
PDB for NP0067199 (Hetidine)
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       2.611   0.250   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.497   1.558   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.768   2.915   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.036   1.574   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.884   0.191   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.111  -1.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.650  -0.821   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.715  -2.698   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.359  -3.305   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.092  -2.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.160  -0.348   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.471  -1.536   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.012  -2.329   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.648  -1.798   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.007  -0.322   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.987  -0.686   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.278   0.153   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.607  -2.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.211  -2.662   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.435  -0.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.973  -0.801   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.462   0.420   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.888  -3.864   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.589   1.131   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.334  -2.690   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.101  -4.823   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15   22                                             
CONECT    6    5    7   19                                                  
CONECT    7    6    1    8   14                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10    1   12   24                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13    7   15                                                  
CONECT   15   14    5   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18    6                                                       
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5                                                       
CONECT   23   13                                                            
CONECT   24   11                                                            
CONECT   25   10                                                            
CONECT   26    9                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

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3D PDB for NP0067199 (Hetidine)
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SMILES for NP0067199 (Hetidine)
CN1C[C@@]2(C)[C@H](O)[C@H](O)C[C@@]34[C@H]1[C@H]1C(=O)[C@H]5C[C@@H]3[C@]1(CC5=C)CC(=O)[C@H]24
Download
INCHI for NP0067199 (Hetidine)
InChI=1S/C21H27NO4/c1-9-5-20-6-11(23)16-19(2)8-22(3)17-14(20)15(25)10(9)4-13(20)21(16,17)7-12(24)18(19)26/h10,12-14,16-18,24,26H,1,4-8H2,2-3H3/t10-,12+,13+,14+,16+,17+,18+,19+,20-,21+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H27NO4
Average Mass357.4500 Da
Monoisotopic Mass357.19401 Da
IUPAC Name(1R,3R,4S,5S,8R,9S,11S,14S,17S,18R)-3,4-dihydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-10,16-dione
Traditional Name(1R,3R,4S,5S,8R,9S,11S,14S,17S,18R)-3,4-dihydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecane-10,16-dione
CAS Registry NumberNot Available
SMILES
CN1C[C@@]2(C)[C@H](O)[C@H](O)C[C@@]34[C@H]1[C@H]1C(=O)[C@H]5C[C@@H]3[C@]1(CC5=C)CC(=O)[C@H]24
InChI Identifier
InChI=1S/C21H27NO4/c1-9-5-20-6-11(23)16-19(2)8-22(3)17-14(20)15(25)10(9)4-13(20)21(16,17)7-12(24)18(19)26/h10,12-14,16-18,24,26H,1,4-8H2,2-3H3/t10-,12+,13+,14+,16+,17+,18+,19+,20-,21+/m0/s1
InChI KeyLHSMCOYXDSMPQS-ACBREKFMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aconitum heterophyllumLOTUS Database
Aconitum heterophyllum Wall.Plant
Delphinium albiflorumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentAtisane diterpenoids  
Alternative Parents
Substituents
  • Atisane diterpenoid
    • 

  • Alkaloid or derivatives
    • 

  • Piperidine
    • 

  • Cyclic alcohol
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • 1,2-diol
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • 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
logP0.25ALOGPS
logP-0.03ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.58ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.84 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.63 m³·mol⁻¹ChemAxon
Polarizability0 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 Compound163104870  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available