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Showing NP-Card for Anhydrocinnzeylanine (NP0048612)

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Record Information
Version2.0
Created at2022-03-17 20:59:14 UTC
Updated at2022-03-17 20:59:14 UTC
NP-MRD IDNP0048612
Secondary Accession NumbersNone
Natural Product Identification
Common NameAnhydrocinnzeylanine
DescriptionAnhydrocinnzeylanine belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Anhydrocinnzeylanine is found in Persea indica. Anhydrocinnzeylanine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048612 (Anhydrocinnzeylanine)


  Mrv1652305221920302D          

 31 34  0  0  1  0            999 V2000
    4.2337    0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569    1.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887    1.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469    2.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4066    2.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474    0.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -0.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598    0.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4248   -0.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6474    1.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654    1.0622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2079    1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    2.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516    0.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399    1.4902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2491   -0.5645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7812    0.2685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7357    0.1018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5182    0.8976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7632    1.0933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7193    3.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122   -0.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770    0.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -0.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    2.3150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329    0.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833    1.8870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    1.9181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  6  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18  6  1  6  0  0  0
 18 10  1  0  0  0  0
 19  8  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 17  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  2  0  0  0  0
 24 16  2  0  0  0  0
 19 25  1  6  0  0  0
 20 26  1  6  0  0  0
 21 27  1  6  0  0  0
 28 14  1  0  0  0  0
 17 28  1  1  0  0  0
 29 16  1  0  0  0  0
 22 29  1  1  0  0  0
 12 30  1  1  0  0  0
 17 31  1  6  0  0  0
M  END
Download

3D MOL for NP0048612 (Anhydrocinnzeylanine)

Download
3D SDF for NP0048612 (Anhydrocinnzeylanine)

  Mrv1652305221920302D          

 31 34  0  0  1  0            999 V2000
    4.2337    0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569    1.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887    1.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469    2.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4066    2.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6382   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474    0.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -0.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5598    0.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4248   -0.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6474    1.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654    1.0622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2079    1.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    2.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8516    0.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399    1.4902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2491   -0.5645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7812    0.2685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7357    0.1018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5182    0.8976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7632    1.0933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7193    3.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122   -0.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770    0.4860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0918   -0.6424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    2.3150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329    0.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833    1.8870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    1.9181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  6  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18  6  1  6  0  0  0
 18 10  1  0  0  0  0
 19  8  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 17  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  2  0  0  0  0
 24 16  2  0  0  0  0
 19 25  1  6  0  0  0
 20 26  1  6  0  0  0
 21 27  1  6  0  0  0
 28 14  1  0  0  0  0
 17 28  1  1  0  0  0
 29 16  1  0  0  0  0
 22 29  1  1  0  0  0
 12 30  1  1  0  0  0
 17 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0048612

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C)CC[C@]2(O)[C@]3(C)CC(=O)O[C@@]2([C@]1([H])OC(C)=O)[C@@]1(O)C(C)=C(C[C@@]31O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O7/c1-11(2)15-9-20(26)18(6)10-16(24)29-22(21(20,27)13(15)4)17(28-14(5)23)12(3)7-8-19(18,22)25/h11-12,17,25-27H,7-10H2,1-6H3/t12-,17+,18-,19-,20+,21+,22+/m0/s1

> <INCHI_KEY>
UEXGXCDLLOHGAS-HKSIISMGSA-N

> <FORMULA>
C22H32O7

> <MOLECULAR_WEIGHT>
408.4853

> <EXACT_MASS>
408.214803378

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.41582076033958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,6R,7R,8S,11S,12R)-2,6,8-trihydroxy-3,7,11-trimethyl-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-12-yl acetate

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.8829596586666685

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.083138203209916

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.896033854579633

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6570925344750185

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
102.35309999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6R,7R,8S,11S,12R)-2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048612 (Anhydrocinnzeylanine)
Download
PDB for NP0048612 (Anhydrocinnzeylanine)
HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       7.903   0.880   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.200   3.453   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.592   2.723   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.194   4.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.626   4.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.058  -2.412   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.208   0.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.265  -0.477   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.778   0.117   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.793  -1.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.808   1.963   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.242   1.983   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.121   2.521   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.309   5.062   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.323   1.557   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.217   0.043   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.075   2.782   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.332  -1.054   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.458   0.501   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.240   0.190   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.834   1.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.425   2.041   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.343   6.602   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.703  -0.363   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.944   0.907   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.905  -1.199   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.583   3.195   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.041   4.321   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.061   1.558   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -1.276   3.522   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.391   3.581   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   18                                                            
CONECT    7    8   12                                                       
CONECT    8    7   19                                                       
CONECT    9   15   20                                                       
CONECT   10   16   18                                                       
CONECT   11    1    2   15                                                  
CONECT   12    3    7   17   30                                             
CONECT   13    4   15   21                                                  
CONECT   14    5   23   28                                                  
CONECT   15    9   11   13                                                  
CONECT   16   10   24   29                                                  
CONECT   17   12   22   28   31                                             
CONECT   18    6   10   19   20                                             
CONECT   19    8   18   22   25                                             
CONECT   20    9   18   21   26                                             
CONECT   21   13   20   22   27                                             
CONECT   22   17   19   21   29                                             
CONECT   23   14                                                            
CONECT   24   16                                                            
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27   21                                                            
CONECT   28   14   17                                                       
CONECT   29   16   22                                                       
CONECT   30   12                                                            
CONECT   31   17                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0048612 (Anhydrocinnzeylanine)
Download
SMILES for NP0048612 (Anhydrocinnzeylanine)
[H][C@]1(C)CC[C@]2(O)[C@]3(C)CC(=O)O[C@@]2([C@]1([H])OC(C)=O)[C@@]1(O)C(C)=C(C[C@@]31O)C(C)C
Download
INCHI for NP0048612 (Anhydrocinnzeylanine)
InChI=1S/C22H32O7/c1-11(2)15-9-20(26)18(6)10-16(24)29-22(21(20,27)13(15)4)17(28-14(5)23)12(3)7-8-19(18,22)25/h11-12,17,25-27H,7-10H2,1-6H3/t12-,17+,18-,19-,20+,21+,22+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC22H32O7
Average Mass408.4853 Da
Monoisotopic Mass408.21480 Da
IUPAC Name(1R,2R,6R,7R,8S,11S,12R)-2,6,8-trihydroxy-3,7,11-trimethyl-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-12-yl acetate
Traditional Name(1R,2R,6R,7R,8S,11S,12R)-2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0^{1,8}.0^{2,6}]pentadec-3-en-12-yl acetate
CAS Registry Number68799-62-2
SMILES
[H][C@]1(C)CC[C@]2(O)[C@]3(C)CC(=O)O[C@@]2([C@]1([H])OC(C)=O)[C@@]1(O)C(C)=C(C[C@@]31O)C(C)C
InChI Identifier
InChI=1S/C22H32O7/c1-11(2)15-9-20(26)18(6)10-16(24)29-22(21(20,27)13(15)4)17(28-14(5)23)12(3)7-8-19(18,22)25/h11-12,17,25-27H,7-10H2,1-6H3/t12-,17+,18-,19-,20+,21+,22+/m0/s1
InChI KeyUEXGXCDLLOHGAS-HKSIISMGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cinnamomum aromaticumFooDB
Persea indicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene lactones  
Alternative Parents
Substituents
  • Terpene lactone
    • 

  • Sesquiterpenoid
    • 

  • Caprolactone
    • 

  • Delta valerolactone
    • 

  • Delta_valerolactone
    • 

  • Oxepane
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Oxane
    • 

  • Cyclic alcohol
    • 

  • Tertiary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • 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
logP1.21ALOGPS
logP0.88ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)11.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.35 m³·mol⁻¹ChemAxon
Polarizability42.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015818  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101316921  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available