NP-MRD: Showing NP-Card for methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate (NP0182330)

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Record Information

Version

2.0

Created at

2022-09-03 20:59:29 UTC

Updated at

2022-09-03 20:59:29 UTC

NP-MRD ID

NP0182330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate

Description

Caesalpinista B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on Caesalpinista B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032222592D          

 29 32  0  0  1  0            999 V2000
   -1.7270   -3.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142   -3.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -2.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -2.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1807   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    0.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7433   -4.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  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  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 27  1  1  0  0  0
  5 29  1  0  0  0  0
 10 29  1  0  0  0  0
M  END


  Mrv1652309032222592D          

 29 32  0  0  1  0            999 V2000
   -1.7270   -3.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142   -3.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -2.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1589   -2.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1807   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    0.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7114   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7433   -4.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  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  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 27  1  1  0  0  0
  5 29  1  0  0  0  0
 10 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)CCC[C@]2(COC(C)=O)[C@H]3CC4=C(C=CO4)[C@H](C)[C@@H]3C[C@@H](O)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O6/c1-13-15-6-9-28-19(15)11-17-16(13)10-18(25)20-22(3,21(26)27-4)7-5-8-23(17,20)12-29-14(2)24/h6,9,13,16-18,20,25H,5,7-8,10-12H2,1-4H3/t13-,16-,17-,18+,20-,22-,23-/m0/s1

> <INCHI_KEY>
CNRDGMAZSRXKTL-AXTFMYCFSA-N

> <FORMULA>
C23H32O6

> <MOLECULAR_WEIGHT>
404.503

> <EXACT_MASS>
404.21988875

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.915364810452886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,2S,6S,7R,8R,10S,11R)-2-[(acetyloxy)methyl]-8-hydroxy-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-6-carboxylate

> <JCHEM_LOGP>
2.692046990333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.880396893164495

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7431692476879435

> <JCHEM_POLAR_SURFACE_AREA>
85.97000000000001

> <JCHEM_REFRACTIVITY>
106.1315

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S,6S,7R,8R,10S,11R)-2-[(acetyloxy)methyl]-8-hydroxy-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.224  -7.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.706  -6.737   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.176  -5.291   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.163  -4.109   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.341  -5.027   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.337  -6.567   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.182  -3.579   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.810  -2.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.326  -2.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.850  -4.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.842  -2.944   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.319  -1.495   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.312  -0.318   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.828  -0.589   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.789   1.130   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.366  -4.392   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.358  -3.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.874  -3.486   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.090  -2.541   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.365  -3.405   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.937  -4.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.398  -4.934   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.405  -6.112   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.928  -7.560   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.889  -5.841   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.896  -7.018   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.380  -6.747   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.387  -7.924   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.857  -5.298   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   29                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₆

Average Mass

404.5030 Da

Monoisotopic Mass

404.21989 Da

IUPAC Name

methyl (1S,2S,6S,7R,8R,10S,11R)-2-[(acetyloxy)methyl]-8-hydroxy-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-6-carboxylate

Traditional Name

methyl (1S,2S,6S,7R,8R,10S,11R)-2-[(acetyloxy)methyl]-8-hydroxy-6,11-dimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)CCC[C@]2(COC(C)=O)[C@H]3CC4=C(C=CO4)[C@H](C)[C@@H]3C[C@@H](O)[C@@H]12

InChI Identifier

InChI=1S/C23H32O6/c1-13-15-6-9-28-19(15)11-17-16(13)10-18(25)20-22(3,21(26)27-4)7-5-8-23(17,20)12-29-14(2)24/h6,9,13,16-18,20,25H,5,7-8,10-12H2,1-4H3/t13-,16-,17-,18+,20-,22-,23-/m0/s1

InChI Key

CNRDGMAZSRXKTL-AXTFMYCFSA-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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthofuran
Benzofuran
Dicarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Furan
Methyl ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen 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	2.69	ChemAxon
pKa (Strongest Acidic)	14.88	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.13 m³·mol⁻¹	ChemAxon
Polarizability	43.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

102036349

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate (NP0182330)

MOL for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

3D MOL for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

3D SDF for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

3D-SDF for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

PDB for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

3D PDB for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

SMILES for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

INCHI for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

Structure for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)

3D Structure for NP0182330 (methyl (4s,4ar,5r,6as,7r,11as,11bs)-11b-[(acetyloxy)methyl]-5-hydroxy-4,7-dimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-carboxylate)