NP-MRD: Showing NP-Card for 3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol (NP0172937)

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Record Information

Version

2.0

Created at

2022-09-03 09:58:48 UTC

Updated at

2022-09-03 09:58:48 UTC

NP-MRD ID

NP0172937

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol

Description

3-[(7-Hydroxy-1,2,4a,8,8a-pentamethyl-tetradecahydrophenanthren-1-yl)methyl]-1H-indol-6-ol belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 3-[(7-Hydroxy-1,2,4a,8,8a-pentamethyl-tetradecahydrophenanthren-1-yl)methyl]-1H-indol-6-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151518152D          

 31 35  0  0  0  0            999 V2000
    2.0759   -0.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006   -1.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -0.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066   -0.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2499   -1.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -1.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -2.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2388   -3.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5364   -3.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684   -2.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -3.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9436   -3.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -3.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -2.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3509   -2.9302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -1.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251   -2.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573   -2.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664   -2.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643   -2.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2193   -3.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -3.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2193   -4.3407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039   -4.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184   -4.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328   -4.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1473   -4.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328   -3.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184   -2.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039   -3.2607    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
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  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  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 10 18  1  0  0  0  0
  7 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 22 31  1  0  0  0  0
 25 31  1  0  0  0  0
M  END


  Mrv1533004151518152D          

 31 35  0  0  0  0            999 V2000
    2.0759   -0.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006   -1.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -0.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066   -0.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2499   -1.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -1.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -2.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2388   -3.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5364   -3.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684   -2.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -3.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9436   -3.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -3.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -2.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3509   -2.9302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -1.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251   -2.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573   -2.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664   -2.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9643   -2.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2193   -3.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -3.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2193   -4.3407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039   -4.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184   -4.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328   -4.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1473   -4.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328   -3.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184   -2.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039   -3.2607    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
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  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  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 10 18  1  0  0  0  0
  7 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 22 31  1  0  0  0  0
 25 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172937

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)C(CCC3(C)C(C)C(O)CCC23)C1(C)CC1=CNC2=CC(O)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C28H41NO2/c1-17-10-12-27(4)24-9-8-23(31)18(2)26(24,3)13-11-25(27)28(17,5)15-19-16-29-22-14-20(30)6-7-21(19)22/h6-7,14,16-18,23-25,29-31H,8-13,15H2,1-5H3

> <INCHI_KEY>
NWKNHNUJGTXAFZ-UHFFFAOYSA-N

> <FORMULA>
C28H41NO2

> <MOLECULAR_WEIGHT>
423.641

> <EXACT_MASS>
423.313729564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.54072935825909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-tetradecahydrophenanthren-1-yl)methyl]-1H-indol-6-ol

> <ALOGPS_LOGP>
6.02

> <JCHEM_LOGP>
6.492314390999999

> <ALOGPS_LOGS>
-6.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.158551502321583

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.524682501520486

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9550129945001661

> <JCHEM_POLAR_SURFACE_AREA>
56.25

> <JCHEM_REFRACTIVITY>
127.02699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2H-phenanthren-1-yl)methyl]-1H-indol-6-ol

> <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       3.875  -1.783   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.428  -2.309   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.248  -1.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.199  -1.846   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.466  -3.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.646  -2.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.713  -4.353   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.446  -5.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.001  -6.396   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.181  -5.406   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.448  -6.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.628  -5.933   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.896  -7.449   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.808  -4.943   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.255  -5.470   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.540  -3.426   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.093  -2.900   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.914  -3.890   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.160  -3.826   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.737  -5.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.667  -4.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.143  -5.611   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.237  -6.857   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       4.143  -8.103   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       5.607  -7.627   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.941  -8.397   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.275  -7.627   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.608  -8.397   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.275  -6.087   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.941  -5.317   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.607  -6.087   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   18                                             
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    5   10                                                  
CONECT   19    7    2   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   22   25                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₁NO₂

Average Mass

423.6410 Da

Monoisotopic Mass

423.31373 Da

IUPAC Name

3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-tetradecahydrophenanthren-1-yl)methyl]-1H-indol-6-ol

Traditional Name

3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2H-phenanthren-1-yl)methyl]-1H-indol-6-ol

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)C(CCC3(C)C(C)C(O)CCC23)C1(C)CC1=CNC2=CC(O)=CC=C12

InChI Identifier

InChI=1S/C28H41NO2/c1-17-10-12-27(4)24-9-8-23(31)18(2)26(24,3)13-11-25(27)28(17,5)15-19-16-29-22-14-20(30)6-7-21(19)22/h6-7,14,16-18,23-25,29-31H,8-13,15H2,1-5H3

InChI Key

NWKNHNUJGTXAFZ-UHFFFAOYSA-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 colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Hydrophenanthrene
Phenanthrene
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Substituted pyrrole
Cyclic alcohol
Heteroaromatic compound
Pyrrole
Secondary alcohol
Azacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	6.02	ALOGPS
logP	6.49	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	9.52	ChemAxon
pKa (Strongest Basic)	-0.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	56.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	127.03 m³·mol⁻¹	ChemAxon
Polarizability	50.54 Å³	ChemAxon
Number of Rings	5	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

73801771

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol (NP0172937)

MOL for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

3D MOL for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

3D SDF for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

3D-SDF for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

PDB for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

3D PDB for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

SMILES for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

INCHI for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

Structure for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)

3D Structure for NP0172937 (3-[(7-hydroxy-1,2,4a,8,8a-pentamethyl-decahydro-2h-phenanthren-1-yl)methyl]-1h-indol-6-ol)