NP-MRD: Showing NP-Card for (1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol (NP0332149)

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Record Information

Version

2.0

Created at

2023-11-29 04:14:08 UTC

Updated at

2024-09-03 04:18:10 UTC

NP-MRD ID

NP0332149

Natural Product DOI

https://doi.org/10.57994/1306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol

Description

(1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on (1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11292304142D          

 24 27  0  0  1  0            999 V2000
   -0.6302   -2.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1539   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781   -0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4630   -3.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23  2  1  0  0  0  0
 23 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0332149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC[C@@]3(O)C(C)(C)C[C@H](O)[C@H](O)[C@]3(C)C2=CC2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-11-12-5-7-20(23)18(2,3)10-15(21)17(22)19(20,4)14(12)9-16-13(11)6-8-24-16/h6,8-9,15,17,21-23H,5,7,10H2,1-4H3/t15-,17-,19-,20+/m0/s1

> <INCHI_KEY>
KCXXCCBXFHRUKN-LWCVALJOSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.62432264001283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4aR,11bS)-4,4,7,11b-tetramethyl-1H,2H,3H,4H,4aH,5H,6H,11bH-phenanthro[3,2-b]furan-1,2,4a-triol

> <JCHEM_LOGP>
2.675500789333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.036783596512837

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.314677410689493

> <JCHEM_PKA_STRONGEST_BASIC>
-2.868123790466718

> <JCHEM_POLAR_SURFACE_AREA>
73.83

> <JCHEM_REFRACTIVITY>
91.66939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aR,11bS)-4,4,7,11b-tetramethyl-1H,2H,3H,5H,6H-phenanthro[3,2-b]furan-1,2,4a-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-NOV-23         0                                  
HETATM    1  C   UNK     0      -1.176  -5.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.341  -5.027   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.337  -6.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.182  -3.579   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.810  -2.402   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.287  -0.953   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.326  -2.673   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.319  -1.495   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.850  -4.121   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.842  -2.944   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.366  -4.392   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.358  -3.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.874  -3.486   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.398  -4.934   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.937  -4.884   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.365  -3.405   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.090  -2.541   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.405  -6.112   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.928  -7.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.889  -5.841   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.896  -7.018   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.380  -6.747   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.857  -5.298   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.864  -6.476   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   23                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   23                                             
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    9    2   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

(1R,2S,4aR,11bS)-4,4,7,11b-tetramethyl-1H,2H,3H,4H,4aH,5H,6H,11bH-phenanthro[3,2-b]furan-1,2,4a-triol

Traditional Name

(1R,2S,4aR,11bS)-4,4,7,11b-tetramethyl-1H,2H,3H,5H,6H-phenanthro[3,2-b]furan-1,2,4a-triol

CAS Registry Number

Not Available

SMILES

CC1=C2CC[C@@]3(O)C(C)(C)C[C@H](O)[C@H](O)[C@]3(C)C2=CC2=C1C=CO2

InChI Identifier

InChI=1S/C20H26O4/c1-11-12-5-7-20(23)18(2,3)10-15(21)17(22)19(20,4)14(12)9-16-13(11)6-8-24-16/h6,8-9,15,17,21-23H,5,7,10H2,1-4H3/t15-,17-,19-,20+/m0/s1

InChI Key

KCXXCCBXFHRUKN-LWCVALJOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Phenanthrene
Naphthofuran
Tetralin
Benzofuran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.68	ChemAxon
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.67 m³·mol⁻¹	ChemAxon
Polarizability	36.62 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol (NP0332149)

MOL for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

3D MOL for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

3D SDF for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

3D-SDF for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

PDB for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

3D PDB for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

SMILES for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

INCHI for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

Structure for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)

3D Structure for NP0332149 ((1R,2S,5R,10S)-8,9,11,14-Didehydrovouacapen-1,2,5-triol)