NP-MRD: Showing NP-Card for 3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol (NP0323225)

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Record Information

Version

2.0

Created at

2022-09-12 02:30:48 UTC

Updated at

2022-09-12 02:30:49 UTC

NP-MRD ID

NP0323225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol

Description

(3Beta,21alphaH)-22(30)-Hopene-3,29-diol belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30) (3beta,21alphaH)-22(30)-Hopene-3,29-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3beta,21alphah)-22(30)-hopene-3,29-diol has been detected, but not quantified in, fruits. 3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol is found in Rhodomyrtus tomentosa. This could make (3beta,21alphah)-22(30)-hopene-3,29-diol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308142D          

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M  END

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M  END


  Mrv0541 05061308142D          

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 21 11  1  0  0  0  0
 21 20  1  0  0  0  0
 22 12  1  0  0  0  0
 23  8  1  0  0  0  0
 24  9  1  0  0  0  0
 25 13  1  0  0  0  0
 26  2  1  0  0  0  0
 26  3  1  0  0  0  0
 26 22  1  0  0  0  0
 26 25  1  0  0  0  0
 27  4  1  0  0  0  0
 27 14  1  0  0  0  0
 27 21  1  0  0  0  0
 27 23  1  0  0  0  0
 28  5  1  0  0  0  0
 28 15  1  0  0  0  0
 28 22  1  0  0  0  0
 28 24  1  0  0  0  0
 29  6  1  0  0  0  0
 29 16  1  0  0  0  0
 29 23  1  0  0  0  0
 30  7  1  0  0  0  0
 30 17  1  0  0  0  0
 30 24  1  0  0  0  0
 30 29  1  0  0  0  0
 31 18  1  0  0  0  0
 32 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC(C1CCC1(C)C2CCC2C3(C)CCC(O)C(C)(C)C3CCC12C)C(=C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O2/c1-19(18-31)20-10-14-27(4)21(20)11-16-29(6)23(27)8-9-24-28(5)15-13-25(32)26(2,3)22(28)12-17-30(24,29)7/h20-25,31-32H,1,8-18H2,2-7H3

> <INCHI_KEY>
SUMUIPKPDFCHLW-UHFFFAOYSA-N

> <FORMULA>
C30H50O2

> <MOLECULAR_WEIGHT>
442.7168

> <EXACT_MASS>
442.381080844

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
55.24387079747561

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(3-hydroxyprop-1-en-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
6.167275324333334

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.48943339017772

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.881471159352557

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8047961541041347

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
132.68299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(3-hydroxyprop-1-en-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.700   2.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.639  -2.953   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.659  -2.983   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.957   4.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.906   2.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.907   0.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.569   1.979   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.550   3.661   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.228   2.871   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.043   5.397   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.585   1.413   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.298  -1.748   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.262   0.501   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.514   5.213   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.584   1.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.264   0.622   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.620  -0.958   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.215   4.863   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.202   3.703   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.691   4.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.562   2.952   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.953  -0.999   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.895   2.912   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.251   1.331   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.286  -1.039   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.631  -1.789   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.217   3.702   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.930   0.541   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.918   1.372   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.596   0.582   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.726   4.566   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.036  -1.829   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   26                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   23                                                       
CONECT    9    8   24                                                       
CONECT   10   14   20                                                       
CONECT   11   16   21                                                       
CONECT   12   17   22                                                       
CONECT   13   15   25                                                       
CONECT   14   10   27                                                       
CONECT   15   13   28                                                       
CONECT   16   11   29                                                       
CONECT   17   12   30                                                       
CONECT   18   19   31                                                       
CONECT   19    1   18   20                                                  
CONECT   20   10   19   21                                                  
CONECT   21   11   20   27                                                  
CONECT   22   12   26   28                                                  
CONECT   23    8   27   29                                                  
CONECT   24    9   28   30                                                  
CONECT   25   13   26   32                                                  
CONECT   26    2    3   22   25                                             
CONECT   27    4   14   21   23                                             
CONECT   28    5   15   22   24                                             
CONECT   29    6   16   23   30                                             
CONECT   30    7   17   24   29                                             
CONECT   31   18                                                            
CONECT   32   25                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3b,21AlphaH)-22(30)-hopene-3,29-diol	Generator
(3Β,21alphah)-22(30)-hopene-3,29-diol	Generator

Chemical Formula

C₃₀H₅₀O₂

Average Mass

442.7168 Da

Monoisotopic Mass

442.38108 Da

IUPAC Name

6-(3-hydroxyprop-1-en-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

Traditional Name

6-(3-hydroxyprop-1-en-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

CAS Registry Number

Not Available

SMILES

CC12CCC(C1CCC1(C)C2CCC2C3(C)CCC(O)C(C)(C)C3CCC12C)C(=C)CO

InChI Identifier

InChI=1S/C30H50O2/c1-19(18-31)20-10-14-27(4)21(20)11-16-29(6)23(27)8-9-24-28(5)15-13-25(32)26(2,3)22(28)12-17-30(24,29)7/h20-25,31-32H,1,8-18H2,2-7H3

InChI Key

SUMUIPKPDFCHLW-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
Rhodomyrtus tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Hopanoids

Alternative Parents

Not Available

Substituents

Not Available

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	5.79	ALOGPS
logP	6.17	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	16.88	ChemAxon
pKa (Strongest Basic)	-0.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.68 m³·mol⁻¹	ChemAxon
Polarizability	55.24 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

HMDB0035111

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013742

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

131751667

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol (NP0323225)

MOL for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D MOL for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D SDF for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D-SDF for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

PDB for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D PDB for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

SMILES for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

INCHI for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

Structure for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D Structure for NP0323225 (3-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-9-ol)