NP-MRD: Showing NP-Card for 2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one (NP0328078)

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Record Information

Version

2.0

Created at

2022-09-12 11:13:23 UTC

Updated at

2022-09-12 11:13:23 UTC

NP-MRD ID

NP0328078

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one

Description

2,10A-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-3,4b,5,6,6a,7,8,9,10,10a-decahydrochrysen-3-one belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one is found in Russula flavida. 2,10A-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-3,4b,5,6,6a,7,8,9,10,10a-decahydrochrysen-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005021511582D          

 31 34  0  0  0  0            999 V2000
    0.5740    0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -0.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414   -1.8171    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
    2.2418   -2.8586    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  0  0  0  0  0  0  0  0  0  0
    4.6525   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  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  0  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 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  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    3.8424   -3.4657    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
    7.8931   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028    0.6576    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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  6 29  1  0  0  0  0
 16 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END


  Mrv1533005021511582D          

 31 34  0  0  0  0            999 V2000
    0.5740    0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -0.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414   -1.8171    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
    2.2418   -2.8586    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  0  0  0  0  0  0  0  0  0  0
    4.6525   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  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  0  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 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  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    3.8424   -3.4657    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
    7.8931   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028    0.6576    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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  6 29  1  0  0  0  0
 16 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328078

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC=CC1(C)CCC2(O)C3=CC=C4C(C)=C(O)C(=O)C=C4C3(C)CCC2(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O3/c1-18(2)8-7-11-25(4)12-15-28(31)23-10-9-20-19(3)24(30)22(29)16-21(20)27(23,6)14-13-26(28,5)17-25/h7-11,16,30-31H,12-15,17H2,1-6H3

> <INCHI_KEY>
SJEIHHJIJLJHOL-UHFFFAOYSA-N

> <FORMULA>
C28H36O3

> <MOLECULAR_WEIGHT>
420.593

> <EXACT_MASS>
420.266445019

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.70281861227787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-3,4b,5,6,6a,7,8,9,10,10a-decahydrochrysen-3-one

> <ALOGPS_LOGP>
6.05

> <JCHEM_LOGP>
4.833637676666666

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.71323243997092

> <JCHEM_PKA_STRONGEST_BASIC>
0.11571675673725268

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
131.875

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5H-chrysen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-MAY-15         0                                  
HETATM    1  C   UNK     0       1.072   1.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.417   0.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.441  -1.103   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.787  -1.852   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.811  -3.392   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.185  -5.336   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.685  -2.104   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.750  -3.268   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
HETATM   28  C   UNK     0       7.172  -6.469   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.734  -0.940   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.739   1.228   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   29                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   27                                             
CONECT   11   10                                                            
CONECT   12   10   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22   12   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   10   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    6                                                       
CONECT   30   16                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₃

Average Mass

420.5930 Da

Monoisotopic Mass

420.26645 Da

IUPAC Name

2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-3,4b,5,6,6a,7,8,9,10,10a-decahydrochrysen-3-one

Traditional Name

2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5H-chrysen-3-one

CAS Registry Number

Not Available

SMILES

CC(C)=CC=CC1(C)CCC2(O)C3=CC=C4C(C)=C(O)C(=O)C=C4C3(C)CCC2(C)C1

InChI Identifier

InChI=1S/C28H36O3/c1-18(2)8-7-11-25(4)12-15-28(31)23-10-9-20-19(3)24(30)22(29)16-21(20)27(23,6)14-13-26(28,5)17-25/h7-11,16,30-31H,12-15,17H2,1-6H3

InChI Key

SJEIHHJIJLJHOL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Russula flavida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Enol
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	6.05	ALOGPS
logP	4.83	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.71	ChemAxon
pKa (Strongest Basic)	0.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.88 m³·mol⁻¹	ChemAxon
Polarizability	49.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

LOTUS database [Link]

Showing NP-Card for 2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one (NP0328078)

MOL for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

3D MOL for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

3D SDF for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

3D-SDF for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

PDB for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

3D PDB for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

SMILES for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

INCHI for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

Structure for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)

3D Structure for NP0328078 (2,10a-dihydroxy-1,4b,6a,8-tetramethyl-8-(4-methylpenta-1,3-dien-1-yl)-6,7,9,10-tetrahydro-5h-chrysen-3-one)