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Showing NP-Card for Adenolin D (NP0077506)

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Record Information
Version2.0
Created at2022-04-28 22:38:55 UTC
Updated at2022-04-28 22:38:55 UTC
NP-MRD IDNP0077506
Secondary Accession NumbersNone
Natural Product Identification
Common NameAdenolin D
DescriptionAdenolin D 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. Adenolin D is found in Isodon adenolomus, Isodon lihsienensis and Rabdosia lihsienensis. Adenolin D was first documented in 2006 (PMID: 16732517). Based on a literature review very few articles have been published on Adenolin D.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0077506 (Adenolin D)


  Mrv1652304292200382D          

 30 34  0  0  1  0            999 V2000
    5.4846   -1.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8904   -0.6161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5555    0.2399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6530    0.4387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1845   -0.3634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4235    0.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8656   -0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7725   -1.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4570   -1.2610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3821   -1.4299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7495   -2.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5997   -2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1990   -1.6309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3448   -0.7843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6836   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7856    0.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163   -0.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7552   -1.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5266   -0.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -2.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6573   -3.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4806   -3.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996   -4.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -0.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106   -0.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6950    0.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8882    0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3221    1.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916    0.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  1  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
  4 29  1  6  0  0  0
  3 30  1  1  0  0  0
M  END
Download

3D MOL for NP0077506 (Adenolin D)

Download
3D SDF for NP0077506 (Adenolin D)

  Mrv1652304292200382D          

 30 34  0  0  1  0            999 V2000
    5.4846   -1.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8904   -0.6161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5555    0.2399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6530    0.4387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1845   -0.3634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4235    0.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8656   -0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7725   -1.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4570   -1.2610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3821   -1.4299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7495   -2.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5997   -2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1990   -1.6309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3448   -0.7843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6836   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7856    0.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1163   -0.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7552   -1.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5266   -0.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -2.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6573   -3.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4806   -3.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996   -4.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941   -0.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106   -0.1127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6950    0.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8882    0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3221    1.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916    0.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  1  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
  4 29  1  6  0  0  0
  3 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0077506

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@@H]1[C@@H]2C[C@]3([C@@H]([C@@H](C2)OC(C)=O)[C@]24CCCC(C)(C)[C@H]2[C@H](O)[C@@]3(O)OC4)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O7/c1-12(24)30-15-8-13-9-22(18(25)14(13)10-28-4)16(15)21-7-5-6-20(2,3)17(21)19(26)23(22,27)29-11-21/h13-17,19,26-27H,5-11H2,1-4H3/t13-,14+,15+,16-,17+,19-,21+,22-,23+/m0/s1

> <INCHI_KEY>
VVSBOWDVUWUVCK-ZTDGPNIRSA-N

> <FORMULA>
C23H34O7

> <MOLECULAR_WEIGHT>
422.518

> <EXACT_MASS>
422.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
83.19415242998735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,5R,6S,8S,9S,10S,11R)-9,10-dihydroxy-6-(methoxymethyl)-12,12-dimethyl-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
1.5106711873333323

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.801177842365831

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.600745905050319

> <JCHEM_PKA_STRONGEST_BASIC>
-3.68076434762986

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
106.3898

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5R,6S,8S,9S,10S,11R)-9,10-dihydroxy-6-(methoxymethyl)-12,12-dimethyl-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0077506 (Adenolin D)
Download
PDB for NP0077506 (Adenolin D)
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      10.238  -2.288   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.129  -1.150   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.504   0.448   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.819   0.819   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.944  -0.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.524   0.053   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.482  -1.123   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.749  -2.675   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.175  -3.329   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.453  -2.354   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.180  -2.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.866  -4.118   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.453  -4.194   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.571  -3.044   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.844  -1.464   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.609  -0.474   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.800   1.054   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.284  -0.918   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.476  -1.893   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.916  -1.347   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.011  -5.400   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.694  -6.780   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.230  -6.880   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.839  -8.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.642  -1.588   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.300  -0.210   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.031   1.507   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.525   1.225   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.201   2.230   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.504   1.618   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
CONECT    2    1    3   11   16                                             
CONECT    3    2    4   26   30                                             
CONECT    4    3    5   29                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   27   28                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11   25                                             
CONECT   11   10    2   12                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13    1   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   10   26                                                       
CONECT   26   25    3                                                       
CONECT   27    6                                                            
CONECT   28    6                                                            
CONECT   29    4                                                            
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

Download
3D PDB for NP0077506 (Adenolin D)
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SMILES for NP0077506 (Adenolin D)
COC[C@@H]1[C@@H]2C[C@]3([C@@H]([C@@H](C2)OC(C)=O)[C@]24CCCC(C)(C)[C@H]2[C@H](O)[C@@]3(O)OC4)C1=O
Download
INCHI for NP0077506 (Adenolin D)
InChI=1S/C23H34O7/c1-12(24)30-15-8-13-9-22(18(25)14(13)10-28-4)16(15)21-7-5-6-20(2,3)17(21)19(26)23(22,27)29-11-21/h13-17,19,26-27H,5-11H2,1-4H3/t13-,14+,15+,16-,17+,19-,21+,22-,23+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC23H34O7
Average Mass422.5180 Da
Monoisotopic Mass422.23045 Da
IUPAC Name(1S,2S,3R,5R,6S,8S,9S,10S,11R)-9,10-dihydroxy-6-(methoxymethyl)-12,12-dimethyl-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate
Traditional Name(1S,2S,3R,5R,6S,8S,9S,10S,11R)-9,10-dihydroxy-6-(methoxymethyl)-12,12-dimethyl-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate
CAS Registry NumberNot Available
SMILES
COC[C@@H]1[C@@H]2C[C@]3([C@@H]([C@@H](C2)OC(C)=O)[C@]24CCCC(C)(C)[C@H]2[C@H](O)[C@@]3(O)OC4)C1=O
InChI Identifier
InChI=1S/C23H34O7/c1-12(24)30-15-8-13-9-22(18(25)14(13)10-28-4)16(15)21-7-5-6-20(2,3)17(21)19(26)23(22,27)29-11-21/h13-17,19,26-27H,5-11H2,1-4H3/t13-,14+,15+,16-,17+,19-,21+,22-,23+/m0/s1
InChI KeyVVSBOWDVUWUVCK-ZTDGPNIRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Isodon adenolomusLOTUS Database
Isodon lihsienensisLOTUS Database
Rabdosia lihsienensisPlant
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
    • 

  • Carboxylic acid ester
    • 

  • Hemiacetal
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organoheterocyclic compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
logP0.48ALOGPS
logP1.51ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.6ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.39 m³·mol⁻¹ChemAxon
Polarizability83.19 ųChemAxon
Number of Rings5ChemAxon
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 IDC00040863  
Chemspider ID35518074  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70698028  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Li LM, Li GY, Huang SX, Xiao WL, Liao X, Lou LG, Ding LS, Sun HD: Antiproliferative ent-Kauranoids from Isodon parvifolius. Planta Med. 2006 Jun;72(8):740-5. doi: 10.1055/s-2006-931608. Epub 2006 May 29. [PubMed:16732517  ]