NP-MRD: Showing NP-Card for Pregnanetriol (NP0338997)

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Record Information

Version

2.0

Created at

2024-09-11 19:10:04 UTC

Updated at

2024-09-11 19:10:05 UTC

NP-MRD ID

NP0338997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pregnanetriol

Description

Pregnanetriol belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Pregnanetriol, or 5β-pregnane-3α,17α,20α-triol, is a steroid and inactive metabolite of progesterone. Pregnanetriol is an extremely weak basic (essentially neutral) compound (based on its pKa). Pregnanetriol has been linked to the inborn metabolic disorders including 11-beta-hydroxylase deficiency. For females:0 To 5 years: < 0.1 Mg/24 hours6 to 9 years: < 0.3 Mg/24 hours10 to 15 years: 0.1 To 0.6 Mg/24 hours16 years and older: 0 To 1.4 Mg/ 24 hours. Urine excretion of pregnanetriol can be measured over a period of 24 hours. Elevated urine pregnanetriol levels suggest adrenogenital syndrome. In monitoring treatment with cortisol replacement, elevated urine pregnanetriol levels indicate insufficient dosage of cortisol.

Structure

MOL SDF PDB SMILES InChI

3032833
  Mrv1652303262014182D          

 28 31  0  0  1  0            999 V2000
    7.0685    1.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7435    0.8984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920   -2.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414   -0.3249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5414    0.5001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8269   -0.7374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1125   -0.3249    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3617   -0.7431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3220    0.7515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3550   -1.6024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8269    0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125    0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3220   -0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8402   -1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8035    0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -2.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5970   -0.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414    1.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833   -2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3681    0.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9904    1.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150   -0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081   -1.6084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9056    2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6113   -0.9812    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011   -1.0630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6840    0.0051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576   -2.2624    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  2 21  1  0  0  0  0
 23  3  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 13  1  0  0  0  0
  4 25  1  6  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 18  1  1  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 26  1  1  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  7 27  1  6  0  0  0
  8 10  1  0  0  0  0
  8 17  1  0  0  0  0
  8 20  1  1  0  0  0
  9 15  1  0  0  0  0
  9 21  1  0  0  0  0
 10 16  1  0  0  0  0
 10 19  1  0  0  0  0
 10 28  1  1  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 22  1  0  0  0  0
 19 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
M  END

3032833
  Mrv1652303262014182D          

 28 31  0  0  1  0            999 V2000
    7.0685    1.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7435    0.8984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920   -2.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414   -0.3249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5414    0.5001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8269   -0.7374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1125   -0.3249    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3617   -0.7431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3220    0.7515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3550   -1.6024    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8269    0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125    0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3220   -0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8402   -1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8035    0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -2.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5970   -0.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5414    1.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5833   -2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3681    0.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9904    1.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150   -0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081   -1.6084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9056    2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6113   -0.9812    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4011   -1.0630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6840    0.0051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576   -2.2624    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  2 21  1  0  0  0  0
 23  3  1  6  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 13  1  0  0  0  0
  4 25  1  6  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 18  1  1  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 26  1  1  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  7 27  1  6  0  0  0
  8 10  1  0  0  0  0
  8 17  1  0  0  0  0
  8 20  1  1  0  0  0
  9 15  1  0  0  0  0
  9 21  1  0  0  0  0
 10 16  1  0  0  0  0
 10 19  1  0  0  0  0
 10 28  1  1  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 22  1  0  0  0  0
 19 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](O)(C(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H36O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h13-18,22-24H,4-12H2,1-3H3/t13?,14-,15-,16-,17+,18+,19+,20+,21+/m1/s1

> <INCHI_KEY>
SCPADBBISMMJAW-HWPIAJDMSA-N

> <FORMULA>
C21H36O3

> <MOLECULAR_WEIGHT>
336.5087

> <EXACT_MASS>
336.266445018

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.00088018408958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7R,10R,11S,14R,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
2.853998557333335

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.109322994199143

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.41738102222639

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569562491413683

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
95.2319

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7R,10R,11S,14R,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3032833                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  O   UNK     0      13.195   2.868   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      16.321   1.677   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.905  -3.767   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.211  -0.606   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.211   0.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.877  -1.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.543  -0.606   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.142  -1.387   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.668   1.403   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.129  -2.991   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.877   1.704   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.543   0.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.668  -1.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.902  -2.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.567   0.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.519  -3.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.714  -0.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.211   2.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.689  -3.838   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.154   0.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.915   2.306   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.255  -1.331   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.242  -3.002   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.757   3.838   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      12.341  -1.832   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      11.949  -1.984   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      10.610   0.010   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.134  -4.223   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   21                                                            
CONECT    3   23                                                            
CONECT    4    5    6   13   25                                             
CONECT    5    4    9   11   18                                             
CONECT    6    4    7   14   26                                             
CONECT    7    6    8   12   27                                             
CONECT    8    7   10   17   20                                             
CONECT    9    1    5   15   21                                             
CONECT   10    8   16   19   28                                             
CONECT   11    5   12                                                       
CONECT   12    7   11                                                       
CONECT   13    4   15                                                       
CONECT   14    6   16                                                       
CONECT   15    9   13                                                       
CONECT   16   10   14                                                       
CONECT   17    8   22                                                       
CONECT   18    5                                                            
CONECT   19   10   23                                                       
CONECT   20    8                                                            
CONECT   21    2    9   24                                                  
CONECT   22   17   23                                                       
CONECT   23    3   19   22                                                  
CONECT   24   21                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28   10                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
5-beta-Pregnane-3,17,20-triol	HMDB
5beta-Pregnane-3alpha,17alpha,20alpha-triol	HMDB

Chemical Formula

C₂₁H₃₆O₃

Average Mass

336.5087 Da

Monoisotopic Mass

336.26645 Da

IUPAC Name

(1S,2S,5R,7R,10R,11S,14R,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

Traditional Name

(1S,2S,5R,7R,10R,11S,14R,15S)-14-(1-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](O)(C(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C21H36O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h13-18,22-24H,4-12H2,1-3H3/t13?,14-,15-,16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

SCPADBBISMMJAW-HWPIAJDMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-hydroxysteroid
17-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
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	3.39	ALOGPS
logP	2.85	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.23 m³·mol⁻¹	ChemAxon
Polarizability	40 Å³	ChemAxon
Number of Rings	4	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

HMDB0006070

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023826

KNApSAcK ID

Not Available

Chemspider ID

2297709

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pregnanetriol

METLIN ID

Not Available

PubChem Compound

3032833

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Pregnanetriol (NP0338997)

MOL for NP0338997 (Pregnanetriol)

3D MOL for NP0338997 (Pregnanetriol)

3D SDF for NP0338997 (Pregnanetriol)

3D-SDF for NP0338997 (Pregnanetriol)

PDB for NP0338997 (Pregnanetriol)

3D PDB for NP0338997 (Pregnanetriol)

SMILES for NP0338997 (Pregnanetriol)

INCHI for NP0338997 (Pregnanetriol)

Structure for NP0338997 (Pregnanetriol)

3D Structure for NP0338997 (Pregnanetriol)