NP-MRD: Showing NP-Card for (1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde (NP0192357)

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Record Information

Version

2.0

Created at

2022-09-04 09:32:52 UTC

Updated at

2022-09-04 09:32:53 UTC

NP-MRD ID

NP0192357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde

Description

(1S,4aS,4bS,8aR,10aR)-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1,2-dicarbaldehyde belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. (1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde is found in Spongia officinalis. Based on a literature review very few articles have been published on (1S,4aS,4bS,8aR,10aR)-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1,2-dicarbaldehyde.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042211322D          

 22 24  0  0  1  0            999 V2000
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  2  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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 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
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
  2 22  1  0  0  0  0
  7 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@@H]1CC[C@]1(C)[C@H]2CC=C(C=O)[C@H]1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-18(2)9-5-10-20(4)16(18)8-11-19(3)15(13-22)14(12-21)6-7-17(19)20/h6,12-13,15-17H,5,7-11H2,1-4H3/t15-,16-,17-,19+,20+/m1/s1

> <INCHI_KEY>
NPOWRDFGFIYMIY-QKMNUUQDSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.98024855439961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,4bS,8aR,10aR)-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1,2-dicarbaldehyde

> <JCHEM_LOGP>
3.8321159090000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.89915996041363

> <JCHEM_PKA_STRONGEST_BASIC>
-4.960267598210371

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
90.0788

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,4bS,8aR,10aR)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthrene-1,2-dicarbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.883  -5.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.831  -6.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.804  -2.516   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494  -6.517   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.724  -7.851   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.954  -6.517   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   22                                             
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(1S,4aS,4bS,8aR,10aR)-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1,2-dicarbaldehyde

Traditional Name

(1S,4aS,4bS,8aR,10aR)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthrene-1,2-dicarbaldehyde

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@@H]1CC[C@]1(C)[C@H]2CC=C(C=O)[C@H]1C=O

InChI Identifier

InChI=1S/C20H30O2/c1-18(2)9-5-10-20(4)16(18)8-11-19(3)15(13-22)14(12-21)6-7-17(19)20/h6,12-13,15-17H,5,7-11H2,1-4H3/t15-,16-,17-,19+,20+/m1/s1

InChI Key

NPOWRDFGFIYMIY-QKMNUUQDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Spongia officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Isocopalane diterpenoid
Steroid
Phenanthrene
Hydrophenanthrene
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.83	ChemAxon
pKa (Strongest Acidic)	15.9	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.08 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

102317956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde (NP0192357)

MOL for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

3D MOL for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

3D SDF for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

3D-SDF for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

PDB for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

3D PDB for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

SMILES for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

INCHI for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

Structure for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)

3D Structure for NP0192357 ((1s,4as,4bs,8ar,10ar)-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthrene-1,2-dicarbaldehyde)