NP-MRD: Showing NP-Card for 6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol (NP0313178)

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Record Information

Version

2.0

Created at

2022-09-11 10:33:03 UTC

Updated at

2022-09-11 10:33:03 UTC

NP-MRD ID

NP0313178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol

Description

6-(Hydroxymethyl)-2,6,10,11-tetramethyl-14-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-15-ene-4,5-diol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol is found in Salvia santolinifolia. 6-(Hydroxymethyl)-2,6,10,11-tetramethyl-14-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-15-ene-4,5-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505372D          

 34 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004201505372D          

 34 38  0  0  0  0            999 V2000
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    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897   -5.1881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -4.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3290   -2.0470    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
  3  4  1  0  0  0  0
  4  5  1  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
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 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
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 17 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C1CCC(C)(O1)C1CCC2(C)C1=CCC1C3(C)CC(O)C(O)C(C)(CO)C3CCC21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-18(2)22-11-15-30(7,34-22)20-10-13-28(5)19(20)8-9-24-26(3)16-21(32)25(33)27(4,17-31)23(26)12-14-29(24,28)6/h8,20-21,23-25,31-33H,9-17H2,1-7H3

> <INCHI_KEY>
XOPJRPHOKFEGKT-UHFFFAOYSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.36335373213588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(hydroxymethyl)-2,6,10,11-tetramethyl-14-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-15-ene-4,5-diol

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
3.8840984559999994

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.827385611066706

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.553793906657997

> <JCHEM_PKA_STRONGEST_BASIC>
-2.787482617442854

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
138.16580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(hydroxymethyl)-2,6,10,11-tetramethyl-14-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-15-ene-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -3.184  -6.221   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.073  -4.685   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.687  -4.014   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.416  -2.498   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.109  -2.287   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.089  -2.860   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.329  -4.740   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.158  -7.782   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.315  -3.568   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.181  -9.684   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.724  -7.984   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.348  -3.821   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6    3                                                       
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   32                                             
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19   20   29                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   25   18   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   12   17   33                                             
CONECT   33   32                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

6-(hydroxymethyl)-2,6,10,11-tetramethyl-14-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-15-ene-4,5-diol

Traditional Name

6-(hydroxymethyl)-2,6,10,11-tetramethyl-14-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-15-ene-4,5-diol

CAS Registry Number

Not Available

SMILES

CC(C)=C1CCC(C)(O1)C1CCC2(C)C1=CCC1C3(C)CC(O)C(O)C(C)(CO)C3CCC21C

InChI Identifier

InChI=1S/C30H48O4/c1-18(2)22-11-15-30(7,34-22)20-10-13-28(5)19(20)8-9-24-26(3)16-21(32)25(33)27(4,17-31)23(26)12-14-29(24,28)6/h8,20-21,23-25,31-33H,9-17H2,1-7H3

InChI Key

XOPJRPHOKFEGKT-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
Salvia santolinifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
3-hydroxysteroid
12-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
Steroid
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	5.4	ALOGPS
logP	3.88	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	138.17 m³·mol⁻¹	ChemAxon
Polarizability	56.36 Å³	ChemAxon
Number of Rings	5	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 6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol (NP0313178)

MOL for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

3D MOL for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

3D SDF for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

3D-SDF for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

PDB for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

3D PDB for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

SMILES for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

INCHI for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

Structure for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)

3D Structure for NP0313178 (6-(hydroxymethyl)-3a,3b,6,9a-tetramethyl-1-[2-methyl-5-(propan-2-ylidene)oxolan-2-yl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthrene-7,8-diol)