NP-MRD: Showing NP-Card for (+)-Caiophoraenin (NP0079820)

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Record Information

Version

2.0

Created at

2022-04-29 00:52:53 UTC

Updated at

2022-04-29 00:52:53 UTC

NP-MRD ID

NP0079820

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Caiophoraenin

Description

Caiophoraenin belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (+)-Caiophoraenin is found in Caiophora coronata. (+)-Caiophoraenin was first documented in 2003 (PMID: 14695811). Based on a literature review very few articles have been published on caiophoraenin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -0.3376    3.4039   -1.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643    2.0773   -1.8435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    1.3388   -0.6672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0342    0.9630   -0.4902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4571   -0.3292   -0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663   -0.6131   -1.4725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480   -1.4971   -0.2640 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4574   -2.3762    0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -0.7983    0.4467 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5705   -1.6934    0.9068 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9285   -2.6754    0.0064 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7083   -0.6743    1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557    0.0995   -0.2442 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2888    1.3850   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6545    1.0815    0.0032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1434    0.0909   -0.6254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2723    4.0567   -2.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215    3.8048   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    3.5296   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    1.9720    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181   -2.0502   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3224   -2.1072    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2355   -3.4578    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5426   -2.2443    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -0.2153    1.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041   -2.0983    1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -3.3469   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6801   -1.1539    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -0.0047    1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1176   -0.5603   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656    1.8153   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974    2.0741    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    0.6249    0.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139   -0.4213   -1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16  3  1  0
 16  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  1
  7 21  1  6
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  1
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  6
M  END


  Mrv1652304292202522D          

 16 17  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  6  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  9 14  1  6  0  0  0
  4 15  1  6  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079820

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1OC(=O)[C@H](C)[C@H]2[C@@H](O)C[C@H](CO)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O5/c1-5-8-7(13)3-6(4-12)9(8)11(15-2)16-10(5)14/h5-9,11-13H,3-4H2,1-2H3/t5-,6-,7+,8+,9+,11+/m1/s1

> <INCHI_KEY>
ZVEZLXLQLYOFMK-DRZZNBKRSA-N

> <FORMULA>
C11H18O5

> <MOLECULAR_WEIGHT>
230.26

> <EXACT_MASS>
230.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.514190223829402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,4aS,5S,7S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-methoxy-4-methyl-octahydrocyclopenta[c]pyran-3-one

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-0.44597782433333366

> <ALOGPS_LOGS>
0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.560824531416557

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.7839070483722

> <JCHEM_PKA_STRONGEST_BASIC>
-2.602523544186223

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
55.13170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,4aS,5S,7S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-methoxy-4-methyl-hexahydro-1H-cyclopenta[c]pyran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.258   2.073   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    9                                                            
CONECT   15    4   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
1alpha-Methoxy-6alpha,10-dihydroxyisoepiiridomyrmecin	MeSH

Chemical Formula

C₁₁H₁₈O₅

Average Mass

230.2600 Da

Monoisotopic Mass

230.11542 Da

IUPAC Name

(1S,4R,4aS,5S,7S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-methoxy-4-methyl-octahydrocyclopenta[c]pyran-3-one

Traditional Name

(1S,4R,4aS,5S,7S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-methoxy-4-methyl-hexahydro-1H-cyclopenta[c]pyran-3-one

CAS Registry Number

Not Available

SMILES

CO[C@H]1OC(=O)[C@H](C)[C@H]2[C@@H](O)C[C@H](CO)[C@H]12

InChI Identifier

InChI=1S/C11H18O5/c1-5-8-7(13)3-6(4-12)9(8)11(15-2)16-10(5)14/h5-9,11-13H,3-4H2,1-2H3/t5-,6-,7+,8+,9+,11+/m1/s1

InChI Key

ZVEZLXLQLYOFMK-DRZZNBKRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Caiophora coronata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Iridoid-skeleton
Bicyclic monoterpenoid
Monoterpenoid
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary 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	-0.61	ALOGPS
logP	-0.45	ChemAxon
logS	0.02	ALOGPS
pKa (Strongest Acidic)	14.78	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.13 m³·mol⁻¹	ChemAxon
Polarizability	23.51 Å³	ChemAxon
Number of Rings	2	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

C00044605

Chemspider ID

2278980

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3009696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Khera S, Woldemichael GM, Singh MP, Suarez E, Timmermann BN: A novel antibacterial iridoid and triterpene from Caiophora coronata. J Nat Prod. 2003 Dec;66(12):1628-31. doi: 10.1021/np030314a. [PubMed:14695811 ]

Showing NP-Card for (+)-Caiophoraenin (NP0079820)

MOL for NP0079820 ((+)-Caiophoraenin)

3D MOL for NP0079820 ((+)-Caiophoraenin)

3D SDF for NP0079820 ((+)-Caiophoraenin)

3D-SDF for NP0079820 ((+)-Caiophoraenin)

PDB for NP0079820 ((+)-Caiophoraenin)

3D PDB for NP0079820 ((+)-Caiophoraenin)

SMILES for NP0079820 ((+)-Caiophoraenin)

INCHI for NP0079820 ((+)-Caiophoraenin)

Structure for NP0079820 ((+)-Caiophoraenin)

3D Structure for NP0079820 ((+)-Caiophoraenin)