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Showing NP-Card for Cinnaterpenoid B (NP0351239)

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Record Information
Version2.0
Created at2025-06-28 18:05:55 UTC
Updated at2025-06-30 17:16:05 UTC
NP-MRD IDNP0351239
Natural Product DOIhttps://doi.org/10.57994/4229
Secondary Accession NumbersNone
Natural Product Identification
Common NameCinnaterpenoid B
DescriptionCinnaterpenoid B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Cinnaterpenoid B was first documented in 2025 (PMID: 40554758). Based on a literature review very few articles have been published on Cinnaterpenoid B.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0351239 (Cinnaterpenoid B)


  Mrv2104 01022311162D          

 19 20  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4256    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
  3 12  1  1  0  0  0
  3 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 13 19  2  0  0  0  0
M  END
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3D MOL for NP0351239 (Cinnaterpenoid B)

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3D SDF for NP0351239 (Cinnaterpenoid B)

  Mrv2104 01022311162D          

 19 20  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4256    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
  3 12  1  1  0  0  0
  3 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 13 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@@H](CC[C@@H](C)[C@@]1(O)C=C[C@@](C)(O)C2=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-9(2)11-6-5-10(3)15(18)8-7-14(4,17)13(16)12(11)15/h7-12,17-18H,5-6H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1

> <INCHI_KEY>
JZKYONUHHQOSHJ-OGMFBOKVSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.216955393374974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4aR,5R,8S,8aS)-2,4a-dihydroxy-2,5-dimethyl-8-(propan-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-one

> <JCHEM_LOGP>
2.4794842143333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.843377886265252

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.824614855347281

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3375158959420683

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.4823

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aR,5R,8S,8aS)-2,4a-dihydroxy-8-isopropyl-2,5-dimethyl-6,7,8,8a-tetrahydro-5H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0351239 (Cinnaterpenoid B)
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PDB for NP0351239 (Cinnaterpenoid B)
HEADER    PROTEIN                                 02-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-JAN-23         0                                  
HETATM    1  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.528   0.677   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.518  -1.037   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10   18                                             
CONECT    3    2    4   12   13                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
CONECT   12    3                                                            
CONECT   13    3   14   19                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17    2                                                       
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

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3D PDB for NP0351239 (Cinnaterpenoid B)
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SMILES for NP0351239 (Cinnaterpenoid B)
[H][C@]12[C@@H](CC[C@@H](C)[C@@]1(O)C=C[C@@](C)(O)C2=O)C(C)C
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INCHI for NP0351239 (Cinnaterpenoid B)
InChI=1S/C15H24O3/c1-9(2)11-6-5-10(3)15(18)8-7-14(4,17)13(16)12(11)15/h7-12,17-18H,5-6H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H24O3
Average Mass252.3540 Da
Monoisotopic Mass252.17254 Da
IUPAC Name(2R,4aR,5R,8S,8aS)-2,4a-dihydroxy-2,5-dimethyl-8-(propan-2-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-one
Traditional Name(2R,4aR,5R,8S,8aS)-2,4a-dihydroxy-8-isopropyl-2,5-dimethyl-6,7,8,8a-tetrahydro-5H-naphthalen-1-one
CAS Registry NumberNot Available
SMILES
[H][C@]12[C@@H](CC[C@@H](C)[C@@]1(O)C=C[C@@](C)(O)C2=O)C(C)C
InChI Identifier
InChI=1S/C15H24O3/c1-9(2)11-6-5-10(3)15(18)8-7-14(4,17)13(16)12(11)15/h7-12,17-18H,5-6H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
InChI KeyJZKYONUHHQOSHJ-OGMFBOKVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)wdzhengqun@163.comJinan universityZhengqun Zhou2025-06-27View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)wdzhengqun@163.comJinan universityZhengqun Zhou2025-06-27View Spectrum
ROESY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)wdzhengqun@163.comJinan universityZhengqun Zhou2025-06-27View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)wdzhengqun@163.comJinan universityZhengqun Zhou2025-06-27View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, C2D6OS, experimental)wdzhengqun@163.comJinan universityZhengqun Zhou2025-06-27View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, C2D6OS, experimental)wdzhengqun@163.comJinan universityZhengqun Zhou2025-06-27View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, C2D6OS, experimental)wdzhengqun@163.comJinan universityZhengqun Zhou2025-06-27View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cinnamomum cassia
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Cadinane sesquiterpenoid
    • 

  • Cyclohexenone
    • 

  • Beta-hydroxy ketone
    • 

  • Acyloin
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP2.48ChemAxon
pKa (Strongest Acidic)12.82ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.48 m³·mol⁻¹ChemAxon
Polarizability28.22 ųChemAxon
Number of Rings2ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yan B, Duan S, Liu Z, Zhang T, Ma J, Wu R, Wei M, Jian Q, Zhao H, Chen G, Ma N, Zheng J, Fan H, Zhou Z, Gao H: Hepatoprotective Ring B-Seco Flavonoids and Sesquiterpenoids from the Bark of Cinnamomum cassia Presl. J Agric Food Chem. 2025 Jun 24. doi: 10.1021/acs.jafc.5c03332. [PubMed:40554758  ] 
  2. DOI: 10.1021/acs.jafc.5c03332
  3. PMID: 40554758