NP-MRD: Showing NP-Card for 4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid (NP0161136)

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Record Information

Version

2.0

Created at

2022-09-02 19:14:37 UTC

Updated at

2022-09-02 19:14:37 UTC

NP-MRD ID

NP0161136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid

Description

4-Hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoic acid belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone. 4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid is found in Abies mariesii. 4-Hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151518352D          

 34 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004151518352D          

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    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 12 34  1  0  0  0  0
 16 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(O)C=C(C)C(O)=O)C1(C)CCC2(C)C1=CCC1C2=CCC2C(C)(C)C(O)CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-18(26(33)34)16-20(31)17-19(2)28(5)14-15-30(7)22-8-10-23-27(3,4)25(32)12-13-29(23,6)21(22)9-11-24(28)30/h8,11,16,19-21,23,25,31-32H,9-10,12-15,17H2,1-7H3,(H,33,34)

> <INCHI_KEY>
RGXBCSRGWBMBCF-UHFFFAOYSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.524037917778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoic acid

> <ALOGPS_LOGP>
6.35

> <JCHEM_LOGP>
5.305632396333334

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.881243487619003

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.62741835629938

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068037541447474

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
138.89399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       3.219  -3.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.211  -4.918   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.688  -6.367   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.172  -6.638   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.180  -5.460   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.649  -8.086   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.133  -8.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.860  -7.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.390  -9.805   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.906 -10.077   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.603 -10.983   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.839  -6.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13   14   34                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   34                                             
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   21   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   18   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   12   16                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0,.0,]heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoate	Generator
4-Hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoate	Generator

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

4-hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoic acid

Traditional Name

4-hydroxy-6-{5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-9,15-dien-14-yl}-2-methylhept-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CC(O)C=C(C)C(O)=O)C1(C)CCC2(C)C1=CCC1C2=CCC2C(C)(C)C(O)CCC12C

InChI Identifier

InChI=1S/C30H46O4/c1-18(26(33)34)16-20(31)17-19(2)28(5)14-15-30(7)22-8-10-23-27(3,4)25(32)12-13-29(23,6)21(22)9-11-24(28)30/h8,11,16,19-21,23,25,31-32H,9-10,12-15,17H2,1-7H3,(H,33,34)

InChI Key

RGXBCSRGWBMBCF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies mariesii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

3-hydroxysteroids

Alternative Parents

Substituents

Steroid acid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
Delta-7-steroid
Medium-chain hydroxy acid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
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	6.35	ALOGPS
logP	5.31	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	138.89 m³·mol⁻¹	ChemAxon
Polarizability	56.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

73657274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid (NP0161136)

MOL for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D MOL for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D SDF for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D-SDF for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

PDB for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D PDB for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

SMILES for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

INCHI for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

Structure for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D Structure for NP0161136 (4-hydroxy-6-{7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)