NP-MRD: Showing NP-Card for (1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol (NP0191728)

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Record Information

Version

2.0

Created at

2022-09-04 08:46:47 UTC

Updated at

2022-09-04 08:46:48 UTC

NP-MRD ID

NP0191728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol

Description

3Beta-hydroxy-4beta-methylfusida-17(20)(16, 21-cis), 24-diene (3beta-hydroxy-protosta-17(20)(16, 21-cis), 24-diene) belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol is found in Cephalosporium caerulens. Based on a literature review very few articles have been published on 3beta-hydroxy-4beta-methylfusida-17(20)(16, 21-cis), 24-diene (3beta-hydroxy-protosta-17(20)(16, 21-cis), 24-diene).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210462D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042210462D          

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 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0191728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C1\CC[C@@]2(C)[C@H]1CC[C@H]1[C@@]3(C)C=C[C@H](O)C(C)(C)[C@@H]3CC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O/c1-20(2)10-9-11-21(3)22-14-18-29(7)23(22)12-13-25-28(6)17-16-26(31)27(4,5)24(28)15-19-30(25,29)8/h10,16-17,23-26,31H,9,11-15,18-19H2,1-8H3/b22-21-/t23-,24-,25-,26-,28-,29-,30-/m0/s1

> <INCHI_KEY>
ALSLQXDARSAWLG-PTZNGALWSA-N

> <FORMULA>
C30H48O

> <MOLECULAR_WEIGHT>
424.713

> <EXACT_MASS>
424.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.28190834936963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,7R,10S,11S,14Z,15S)-2,6,6,10,11-pentamethyl-14-(6-methylhept-5-en-2-ylidene)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-5-ol

> <JCHEM_LOGP>
7.500658324333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.695201355838467

> <JCHEM_PKA_STRONGEST_BASIC>
-1.182518926956254

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
135.50729999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7R,10S,11S,14Z,15S)-2,6,6,10,11-pentamethyl-14-(6-methylhept-5-en-2-ylidene)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      10.031   9.731   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.612   8.305   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.137   8.094   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.666   7.089   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.247   5.662   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.302   4.447   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.407   2.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.505  -1.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.939  -1.292   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.341  -2.124   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.521  -1.452   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   17   22   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
3b-Hydroxy-4b-methylfusida-17(20)(16, 21-cis), 24-diene (3b-hydroxy-protosta-17(20)(16, 21-cis), 24-diene)	Generator
3Β-hydroxy-4β-methylfusida-17(20)(16, 21-cis), 24-diene (3β-hydroxy-protosta-17(20)(16, 21-cis), 24-diene)	Generator

Chemical Formula

C₃₀H₄₈O

Average Mass

424.7130 Da

Monoisotopic Mass

424.37052 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C1\CC[C@@]2(C)[C@H]1CC[C@H]1[C@@]3(C)C=C[C@H](O)C(C)(C)[C@@H]3CC[C@]21C

InChI Identifier

InChI=1S/C30H48O/c1-20(2)10-9-11-21(3)22-14-18-29(7)23(22)12-13-25-28(6)17-16-26(31)27(4,5)24(28)15-19-30(25,29)8/h10,16-17,23-26,31H,9,11-15,18-19H2,1-8H3/b22-21-/t23-,24-,25-,26-,28-,29-,30-/m0/s1

InChI Key

ALSLQXDARSAWLG-PTZNGALWSA-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
Cephalosporium caerulens	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-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-1-steroid
Steroid
Delta-1-steroid
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

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

78437918

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol (NP0191728)

MOL for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

PDB for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

Structure for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0191728 ((1z,3as,3bs,5ar,7s,9ar,9bs,11as)-3a,3b,6,6,9a-pentamethyl-1-(6-methylhept-5-en-2-ylidene)-2h,3h,4h,5h,5ah,7h,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol)