NP-MRD: Showing NP-Card for (+)-Ricciocarpin A (NP0058228)

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Record Information

Version

2.0

Created at

2022-04-28 03:35:42 UTC

Updated at

2022-04-28 03:35:42 UTC

NP-MRD ID

NP0058228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Ricciocarpin A

Description

Ricciocarpin A belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (+)-Ricciocarpin A is found in Ricciocarpos natans. (+)-Ricciocarpin A was first documented in 2003 (PMID: 12735765). Based on a literature review a small amount of articles have been published on ricciocarpin A (PMID: 31489999) (PMID: 21378852) (PMID: 16381590).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.6183   -1.2783   -1.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549    0.0455   -0.7725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2963    1.1231   -1.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444    0.3548   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0942   -0.3869    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -0.0975    2.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6788   -0.5914    1.4978 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4706   -0.2676    2.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -0.1527    3.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933   -0.0878    1.7585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634   -0.6618    0.5164 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0753    0.1197   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1799    1.4893   -0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537    1.7733   -0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172    0.6305   -1.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1926   -0.3615   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -0.7490   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.0139    0.1543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4925   -1.2680   -2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -1.2784   -2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941   -2.1380   -0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2014    0.7273   -2.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811    1.7088   -1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271    1.8738   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388    1.4519    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6744    0.1974   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760   -1.4646    1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0107    0.0326    1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9094    0.9789    2.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148   -0.6764    3.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7017   -1.6894    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -1.6755    0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4581    2.1837    0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    2.7634   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725   -1.4363   -0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307   -0.4373   -1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844   -1.8310   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424    1.0616    0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 18  1  0
 18 17  1  0
 17 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
 11 12  1  0
 12 16  2  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 18  2  1  0
 13 12  1  0
  8  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
 18 38  1  1
 17 36  1  0
 17 37  1  0
 11 32  1  1
 16 35  1  0
 14 34  1  0
 13 33  1  0
M  END


  Mrv1652304282205352D          

 18 20  0  0  1  0            999 V2000
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9441    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.9920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1636    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6116   -0.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  3  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 14 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@H]2[C@H]1C[C@H](OC2=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-15(2)6-3-4-11-12(15)8-13(18-14(11)16)10-5-7-17-9-10/h5,7,9,11-13H,3-4,6,8H2,1-2H3/t11-,12+,13-/m0/s1

> <INCHI_KEY>
FFADPQLZGWESJY-XQQFMLRXSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.44609538501581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aR,8aS)-3-(furan-3-yl)-5,5-dimethyl-octahydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.3610886966666667

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8886044635732637

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
67.2519

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aR,8aS)-3-(furan-3-yl)-5,5-dimethyl-hexahydro-3H-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.496   1.532   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.002   1.852   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.772   0.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.742  -0.626   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7    8                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(3S,4aR,8aS)-3-(furan-3-yl)-5,5-dimethyl-octahydro-1H-2-benzopyran-1-one

Traditional Name

(3S,4aR,8aS)-3-(furan-3-yl)-5,5-dimethyl-hexahydro-3H-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@H]2[C@H]1C[C@H](OC2=O)C1=COC=C1

InChI Identifier

InChI=1S/C15H20O3/c1-15(2)6-3-4-11-12(15)8-13(18-14(11)16)10-5-7-17-9-10/h5,7,9,11-13H,3-4,6,8H2,1-2H3/t11-,12+,13-/m0/s1

InChI Key

FFADPQLZGWESJY-XQQFMLRXSA-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
Ricciocarpos natans	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Delta valerolactone
Delta_valerolactone
Oxane
Furan
Heteroaromatic compound
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	3.9	ALOGPS
logP	3.36	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.25 m³·mol⁻¹	ChemAxon
Polarizability	27.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00011571

Chemspider ID

9033118

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10857827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Luo HY, Dong JW, Xie YY, Song XF, Zhu D, Ding T, Liu Y, Chen ZM: Lewis Base/Bronsted Acid Co-Catalyzed Asymmetric Thiolation of Alkenes with Acid-Controlled Divergent Regioselectivity. Chemistry. 2019 Dec 2;25(67):15411-15418. doi: 10.1002/chem.201904028. Epub 2019 Nov 6. [PubMed:31489999 ]
Michrowska A, List B: Concise synthesis of ricciocarpin A and discovery of a more potent analogue. Nat Chem. 2009 Jun;1(3):225-8. doi: 10.1038/nchem.215. Epub 2009 May 22. [PubMed:21378852 ]
Jan NW, Liu HJ: An enantioselective total synthesis of (+)-ricciocarpin A. Org Lett. 2006 Jan 5;8(1):151-3. doi: 10.1021/ol052638r. [PubMed:16381590 ]
Agapiou K, Krische MJ: Catalytic crossed Michael cycloisomerization of thioenoates: total synthesis of (+/-)-ricciocarpin A. Org Lett. 2003 May 15;5(10):1737-40. doi: 10.1021/ol030035e. [PubMed:12735765 ]

Showing NP-Card for (+)-Ricciocarpin A (NP0058228)

MOL for NP0058228 ((+)-Ricciocarpin A)

3D MOL for NP0058228 ((+)-Ricciocarpin A)

3D SDF for NP0058228 ((+)-Ricciocarpin A)

3D-SDF for NP0058228 ((+)-Ricciocarpin A)

PDB for NP0058228 ((+)-Ricciocarpin A)

3D PDB for NP0058228 ((+)-Ricciocarpin A)

SMILES for NP0058228 ((+)-Ricciocarpin A)

INCHI for NP0058228 ((+)-Ricciocarpin A)

Structure for NP0058228 ((+)-Ricciocarpin A)

3D Structure for NP0058228 ((+)-Ricciocarpin A)