NP-MRD: Showing NP-Card for all-trans-18-Hydroxyretinoic acid (NP0092151)

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Record Information

Version

2.0

Created at

2022-05-11 18:58:43 UTC

Updated at

2022-05-11 18:58:43 UTC

NP-MRD ID

NP0092151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

all-trans-18-Hydroxyretinoic acid

Description

All-trans-18-Hydroxyretinoic acid, also known as 18-hydroxyretinoate or 18-hydroxy-all-trans-retinoic acid, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. A retinoid that consists of all-trans-retinoic acid bearing an hydroxy substituent at position 18. All-trans-18-Hydroxyretinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. All-trans-18-hydroxyretinoic acid can be biosynthesized from all-trans-retinoic acid through its interaction with the enzyme cytochrome P450 26A1. all-trans-18-Hydroxyretinoic acid was first documented in 1991 (PMID: 1932598). In humans, all-trans-18-hydroxyretinoic acid is involved in retinol metabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 51  0  0  0  0  0  0  0  0999 V2000
    1.3349   -1.7265    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689   -0.2988    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724    0.1001    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -0.7263    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7731   -0.4520    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6005   -1.4929    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155   -2.8601    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6712   -3.7186   -0.1598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880   -1.3421    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5345   -0.0608    1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4519    0.9562    1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4610    0.8180    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2807    0.7579   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7056    2.0904    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    0.5834   -0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3995    0.2313   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3406    1.1247   -0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7814    0.8331   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523   -0.4916   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081    1.8456   -0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0307    1.6572   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6508    0.5784   -0.6964 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8365    2.7845   -1.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -2.0797    0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262   -2.0492    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029   -2.2829   -0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    1.1023   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9917   -1.7611    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250   -3.2494    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731   -3.0704    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7895   -3.1815   -0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4926   -2.1913    1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5102   -1.5217   -0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8749   -0.2608    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4511    0.2859    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9051    1.9629    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8910    0.8261    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9834    1.5885   -1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0463   -0.1809   -1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3660    0.7785   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    2.3035    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327    2.9061    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793    2.3878   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676    1.6228   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7009   -0.7709   -0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    2.1368   -0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6217   -1.2975   -0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0701   -0.5423    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9440   -0.8902   -1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    2.8568   -0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1898    3.3807   -0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END


  Mrv1652307161916582D          

 23 23  0  0  0  0            999 V2000
 9997.871610000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5856 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299610000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0146 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.730310000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4439 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.157510000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8711 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.584710000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3003 9999.9695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.584710001.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.157510001.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299610001.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.445610001.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.731610001.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4399 9998.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9698 9999.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.444310000.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7298 9999.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7298 9999.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4443 9998.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1588 9999.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1588 9999.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 14 15  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  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 17  1  0  0  0  0
 22 16  1  0  0  0  0
 18 14  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0092151

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+

> <INCHI_KEY>
XSJOIRFEYHJNAW-FCKHSPHMSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.46980704772441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
3.7335965543333325

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.25421877581346

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.996647812346559

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8128047748082965

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
99.56549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JUL-19         0                                  
HETATM    1  C   UNK     0    8662.6948667.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0268666.610   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.3598667.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.6948666.610   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.0308667.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.3628666.610   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.6948667.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.0268666.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.3588667.381   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8674.6948666.610   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8673.3588668.921   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8670.6948668.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3598668.921   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.0328668.921   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8658.6998669.687   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8661.8888663.627   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.8778665.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.0298667.381   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.6968666.611   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8658.6968665.071   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8660.0298664.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8661.3638665.071   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8661.3638666.611   0.000  0.00  0.00           C+0
CONECT    1    2   23                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7                                                            
CONECT   13    3                                                            
CONECT   14   15   18                                                       
CONECT   15   14                                                            
CONECT   16   22                                                            
CONECT   17   22                                                            
CONECT   18   19   23   14                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   17   16                                             
CONECT   23   18   22    1                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
18-Hydroxy-all-trans-retinoic acid	ChEBI
18-Hydroxyretinoic acid	ChEBI
all-trans-9-(2-(Hydroxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid	ChEBI
18-Hydroxy-all-trans-retinoate	Generator
18-Hydroxyretinoate	Generator
all-trans-9-(2-(Hydroxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraenoate	Generator
all-trans-18-Hydroxyretinoate	Generator
rac-18-Hydroxy-all-trans-retinoate	HMDB
rac-18-Hydroxy-all-trans-retinoic acid	HMDB
all-trans-18-Hydroxyretinoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4345 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+

InChI Key

XSJOIRFEYHJNAW-FCKHSPHMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:80657 )
Retinoids (C16679 )

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	4.79	ALOGPS
logP	3.73	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	37.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012452

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029068

KNApSAcK ID

Not Available

Chemspider ID

5005673

KEGG Compound ID

C16679

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6506224

PDB ID

Not Available

ChEBI ID

80657

Good Scents ID

Not Available

References

General References

Napoli JL, Posch KP, Fiorella PD, Boerman MH: Physiological occurrence, biosynthesis and metabolism of retinoic acid: evidence for roles of cellular retinol-binding protein (CRBP) and cellular retinoic acid-binding protein (CRABP) in the pathway of retinoic acid homeostasis. Biomed Pharmacother. 1991;45(4-5):131-43. [PubMed:1932598 ]

Showing NP-Card for all-trans-18-Hydroxyretinoic acid (NP0092151)

MOL for NP0092151 (all-trans-18-Hydroxyretinoic acid)

3D MOL for NP0092151 (all-trans-18-Hydroxyretinoic acid)

3D SDF for NP0092151 (all-trans-18-Hydroxyretinoic acid)

3D-SDF for NP0092151 (all-trans-18-Hydroxyretinoic acid)

PDB for NP0092151 (all-trans-18-Hydroxyretinoic acid)

3D PDB for NP0092151 (all-trans-18-Hydroxyretinoic acid)

SMILES for NP0092151 (all-trans-18-Hydroxyretinoic acid)

INCHI for NP0092151 (all-trans-18-Hydroxyretinoic acid)

Structure for NP0092151 (all-trans-18-Hydroxyretinoic acid)

3D Structure for NP0092151 (all-trans-18-Hydroxyretinoic acid)