NP-MRD: Showing NP-Card for [(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate (NP0232023)

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Record Information

Version

2.0

Created at

2022-09-06 13:06:50 UTC

Updated at

2022-09-06 13:06:50 UTC

NP-MRD ID

NP0232023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate

Description

[(1S,4aS,4bS,8aR,10aR)-2-formyl-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl acetate 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)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate is found in Spongia officinalis. Based on a literature review very few articles have been published on [(1S,4aS,4bS,8aR,10aR)-2-formyl-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062215062D          

 25 27  0  0  1  0            999 V2000
   -2.1730   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  2  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
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.3480    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  1  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
    2.7770   -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
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -3.5894    0.0000 C   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
    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END


  Mrv1652309062215062D          

 25 27  0  0  1  0            999 V2000
   -2.1730   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  2  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
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.3480    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  1  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
    2.7770   -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
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -3.5894    0.0000 C   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
    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0232023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@H]1C(C=O)=CC[C@@H]2[C@@]1(C)CC[C@@H]1C(C)(C)CCC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O3/c1-15(24)25-14-17-16(13-23)7-8-19-21(17,4)12-9-18-20(2,3)10-6-11-22(18,19)5/h7,13,17-19H,6,8-12,14H2,1-5H3/t17-,18-,19-,21+,22+/m1/s1

> <INCHI_KEY>
JIALFXUXKBYDJT-MWGJNXKLSA-N

> <FORMULA>
C22H34O3

> <MOLECULAR_WEIGHT>
346.511

> <EXACT_MASS>
346.250794955

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
39.78256337444022

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,4aS,4bS,8aR,10aR)-2-formyl-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl acetate

> <JCHEM_LOGP>
4.1374072680000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.672678338177539

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
100.31609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4aS,4bS,8aR,10aR)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthren-1-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.056  -7.851   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.516  -7.851   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.746  -9.185   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.746  -6.517   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.206  -6.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.516  -2.516   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.171  -5.710   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.456  -6.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -6.517   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   15   21                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   13   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    6   12   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
[(1S,4AS,4BS,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₃

Average Mass

346.5110 Da

Monoisotopic Mass

346.25079 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@H]1C(C=O)=CC[C@@H]2[C@@]1(C)CC[C@@H]1C(C)(C)CCC[C@]21C

InChI Identifier

InChI=1S/C22H34O3/c1-15(24)25-14-17-16(13-23)7-8-19-21(17,4)12-9-18-20(2,3)10-6-11-22(18,19)5/h7,13,17-19H,6,8-12,14H2,1-5H3/t17-,18-,19-,21+,22+/m1/s1

InChI Key

JIALFXUXKBYDJT-MWGJNXKLSA-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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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

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

163049519

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)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate (NP0232023)

MOL for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

3D MOL for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

3D SDF for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

3D-SDF for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

PDB for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

3D PDB for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

SMILES for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

INCHI for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

Structure for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)

3D Structure for NP0232023 ([(1s,4as,4bs,8ar,10ar)-2-formyl-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-1-yl]methyl acetate)