NP-MRD: Showing NP-Card for 2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol (NP0141537)

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Record Information

Version

2.0

Created at

2022-09-01 19:52:56 UTC

Updated at

2022-09-01 19:52:56 UTC

NP-MRD ID

NP0141537

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol

Description

Cucurbitaxanthin A belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Cucurbitaxanthin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cucurbitaxanthin A has been detected, but not quantified in, several different foods, such as yellow bell peppers, fruits, pepper (c. Annuum), winter squash, and orange bell peppers. 2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol is found in Ganoderma sinense. This could make cucurbitaxanthin a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308222D          

 33 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061308222D          

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    0.3604    2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4067   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20  8  1  0  0  0  0
 21  9  2  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 12  1  0  0  0  0
 22 20  1  0  0  0  0
 23 13  2  0  0  0  0
 24 10  2  0  0  0  0
 24 23  1  0  0  0  0
 25 11  1  0  0  0  0
 26 14  1  0  0  0  0
 27  2  1  0  0  0  0
 27  3  1  0  0  0  0
 27 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28  4  1  0  0  0  0
 28 15  1  0  0  0  0
 28 23  1  0  0  0  0
 28 25  1  0  0  0  0
 29  5  1  0  0  0  0
 29 17  1  0  0  0  0
 29 22  1  0  0  0  0
 30  6  1  0  0  0  0
 30 16  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 19  1  0  0  0  0
 33 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141537

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(CO)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-20(8-7-9-21(18-31)19-32)22-12-16-30(6)24-10-11-25-27(2,3)26(33)14-15-28(25,4)23(24)13-17-29(22,30)5/h9-10,13,20,22,25-26,31-33H,7-8,11-12,14-19H2,1-6H3

> <INCHI_KEY>
LIJZGBVDQCTWLG-UHFFFAOYSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.7003

> <EXACT_MASS>
456.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.4032890822696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}pentylidene)propane-1,3-diol

> <ALOGPS_LOGP>
6.42

> <JCHEM_LOGP>
4.7832085509999995

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.48615577780036

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.796181198441268

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7785394526847346

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
139.21069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}pentylidene)propane-1,3-diol

> <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       6.559   2.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.520  -4.434   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.382  -3.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.488   0.179   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.792   0.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.356  -3.399   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.508   1.715   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.453   0.499   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.983   1.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.026  -3.624   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.542  -3.895   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.496  -1.985   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.972   0.451   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.520  -0.363   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.004  -0.092   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.771  -2.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.456   0.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.488   2.510   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.618   4.147   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.979   0.710   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.037   2.720   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.924  -0.506   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.495  -0.998   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.503  -2.175   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.534  -2.717   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.043  -1.811   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.050  -2.988   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.011  -1.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.463  -0.456   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.987  -1.904   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.433   3.725   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.673   5.363   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.559  -2.082   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   27                                                            
CONECT    3   27                                                            
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7    8    9                                                       
CONECT    8    7   20                                                       
CONECT    9    7   21                                                       
CONECT   10   11   24                                                       
CONECT   11   10   25                                                       
CONECT   12   16   22                                                       
CONECT   13   17   23                                                       
CONECT   14   15   26                                                       
CONECT   15   14   28                                                       
CONECT   16   12   30                                                       
CONECT   17   13   29                                                       
CONECT   18   21   31                                                       
CONECT   19   21   32                                                       
CONECT   20    1    8   22                                                  
CONECT   21    9   18   19                                                  
CONECT   22   12   20   29                                                  
CONECT   23   13   24   28                                                  
CONECT   24   10   23   30                                                  
CONECT   25   11   27   28                                                  
CONECT   26   14   27   33                                                  
CONECT   27    2    3   25   26                                             
CONECT   28    4   15   23   25                                             
CONECT   29    5   17   22   30                                             
CONECT   30    6   16   24   29                                             
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   26                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3S,3'r,5R,6R)-3,6-Epoxy-5,6-dihydro-3',5-dihydroxy-beta,beta-carotene	HMDB
3,6-Epoxy-5,6-dihydro-b,b-carotene-3',5-diol	HMDB
Zeaxanthin 3,6-epoxide (incorr.)	HMDB
(3beta)-Lanosta-7,9(11),24-triene-3,26,27-triol	HMDB
Lanosta-7,9(11),24-triene-3,26,27-triol	HMDB
Ganodermatriol	MeSH

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7003 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

2-(4-{5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}pentylidene)propane-1,3-diol

Traditional Name

2-(4-{5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}pentylidene)propane-1,3-diol

CAS Registry Number

Not Available

SMILES

CC(CCC=C(CO)CO)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C

InChI Identifier

InChI=1S/C30H48O3/c1-20(8-7-9-21(18-31)19-32)22-12-16-30(6)24-10-11-25-27(2,3)26(33)14-15-28(25,4)23(24)13-17-29(22,30)5/h9-10,13,20,22,25-26,31-33H,7-8,11-12,14-19H2,1-6H3

InChI Key

LIJZGBVDQCTWLG-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
Ganoderma sinense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Monosaccharide
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	6.42	ALOGPS
logP	4.78	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.8	ChemAxon
pKa (Strongest Basic)	-0.78	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	6	ChemAxon
Refractivity	139.21 m³·mol⁻¹	ChemAxon
Polarizability	55.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0035319

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013989

KNApSAcK ID

C00022948

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

131751704

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol (NP0141537)

MOL for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

3D MOL for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

3D SDF for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

3D-SDF for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

PDB for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

3D PDB for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

SMILES for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

INCHI for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

Structure for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)

3D Structure for NP0141537 (2-(4-{7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentylidene)propane-1,3-diol)