NP-MRD: Showing NP-Card for [(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid (NP0213542)

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Record Information

Version

1.0

Created at

2022-09-05 12:33:45 UTC

Updated at

2022-09-05 12:33:45 UTC

NP-MRD ID

NP0213542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid

Description

2-[(4AS,4bS,6aR,10aS,10bS,12aS)-4b,7,7,10a-tetramethyl-3-oxo-3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysen-2-yl]acetic acid belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. [(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid is found in Petrosaspongia nigra. Based on a literature review very few articles have been published on 2-[(4aS,4bS,6aR,10aS,10bS,12aS)-4b,7,7,10a-tetramethyl-3-oxo-3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysen-2-yl]acetic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052214332D          

 27 30  0  0  1  0            999 V2000
    2.5944   -3.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5965   -3.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6525   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5133   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235   -2.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -3.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4332   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2728   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -3.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    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  1  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  6  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
  2 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END


  Mrv1652309052214332D          

 27 30  0  0  1  0            999 V2000
    2.5944   -3.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5965   -3.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6525   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5133   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3235   -2.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433   -3.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4332   -3.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2728   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -3.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    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  1  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  6  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
  2 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213542

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@@H]1CC[C@@]1(C)[C@H]3CC(=O)C(CC(O)=O)=C[C@@H]3CC[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O3/c1-22(2)9-5-10-24(4)19(22)8-11-23(3)17-14-18(25)16(13-21(26)27)12-15(17)6-7-20(23)24/h12,15,17,19-20H,5-11,13-14H2,1-4H3,(H,26,27)/t15-,17-,19+,20-,23-,24-/m0/s1

> <INCHI_KEY>
PRNTZJVEEUQNTM-ZYDLNPGJSA-N

> <FORMULA>
C24H36O3

> <MOLECULAR_WEIGHT>
372.549

> <EXACT_MASS>
372.266445019

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
43.411707670310996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(4aS,4bS,6aR,10aS,10bS,12aS)-4b,7,7,10a-tetramethyl-3-oxo-3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysen-2-yl]acetic acid

> <JCHEM_LOGP>
5.191404459999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.288322852456278

> <JCHEM_PKA_STRONGEST_BASIC>
-5.605906717900671

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
107.42909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(4aS,4bS,6aR,10aS,10bS,12aS)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.843  -6.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.714  -6.744   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.685  -2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.750  -3.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.758  -4.432   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      19.270  -4.141   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      17.254  -5.887   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.742  -6.178   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.709  -5.596   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.197  -5.887   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   27                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   27                                             
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   12   23                                                  
CONECT   23   22    9   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
2-[(4AS,4BS,6ar,10as,10BS,12as)-4b,7,7,10a-tetramethyl-3-oxo-3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysen-2-yl]acetate	Generator

Chemical Formula

C₂₄H₃₆O₃

Average Mass

372.5490 Da

Monoisotopic Mass

372.26645 Da

IUPAC Name

2-[(4aS,4bS,6aR,10aS,10bS,12aS)-4b,7,7,10a-tetramethyl-3-oxo-3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysen-2-yl]acetic acid

Traditional Name

[(4aS,4bS,6aR,10aS,10bS,12aS)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@@H]1CC[C@@]1(C)[C@H]3CC(=O)C(CC(O)=O)=C[C@@H]3CC[C@H]21

InChI Identifier

InChI=1S/C24H36O3/c1-22(2)9-5-10-24(4)19(22)8-11-23(3)17-14-18(25)16(13-21(26)27)12-15(17)6-7-20(23)24/h12,15,17,19-20H,5-11,13-14H2,1-4H3,(H,26,27)/t15-,17-,19+,20-,23-,24-/m0/s1

InChI Key

PRNTZJVEEUQNTM-ZYDLNPGJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petrosaspongia nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	5.19	ChemAxon
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.43 m³·mol⁻¹	ChemAxon
Polarizability	43.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162940513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid (NP0213542)

MOL for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

3D MOL for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

3D SDF for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

3D-SDF for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

PDB for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

3D PDB for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

SMILES for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

INCHI for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

Structure for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)

3D Structure for NP0213542 ([(4as,4bs,6ar,10as,10bs,12as)-4b,7,7,10a-tetramethyl-3-oxo-4,4a,5,6,6a,8,9,10,10b,11,12,12a-dodecahydrochrysen-2-yl]acetic acid)