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Showing NP-Card for Scleroderolide (NP0351300)

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Record Information
Version2.0
Created at2025-07-08 22:03:50 UTC
Updated at2025-07-29 03:36:35 UTC
NP-MRD IDNP0351300
Natural Product DOIhttps://doi.org/10.57994/4292
Secondary Accession NumbersNone
Natural Product Identification
Common NameScleroderolide
Description Scleroderolide was first documented in 2015 (PMID: 26582262). Based on a literature review a small amount of articles have been published on Scleroderolide (PMID: 29734036) (PMID: 33279250) (PMID: 32093426) (PMID: 25658054).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0351300 (Scleroderolide)


  Mrv2104 01122315142D          

 24 27  0  0  0  0            999 V2000
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 O   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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0214   -2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
Download

3D MOL for NP0351300 (Scleroderolide)

Download
3D SDF for NP0351300 (Scleroderolide)

  Mrv2104 01122315142D          

 24 27  0  0  0  0            999 V2000
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 O   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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0214   -2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC2=C(C(O)=C3C(=O)C(=O)OC4=C(O)C=C(C)C2=C34)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1/C18H16O6/c1-6-5-8(19)15-10-9(6)16-12(18(3,4)7(2)23-16)13(20)11(10)14(21)17(22)24-15/h5,7,19-20H,1-4H3

> <INCHI_KEY>
MYDJDVOVZVSVIE-UHFFFAOYNA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.04517045529613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(15),5,7,9(16),10(14)-pentaene-2,3-dione

> <JCHEM_LOGP>
4.791960946

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.604572654675453

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.375614077733102

> <JCHEM_PKA_STRONGEST_BASIC>
-4.776451491020046

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
85.25889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(15),5,7,9(16),10(14)-pentaene-2,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0351300 (Scleroderolide)
Download
PDB for NP0351300 (Scleroderolide)
HEADER    PROTEIN                                 12-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-JAN-23         0                                  
HETATM    1  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.507  -4.193   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.578  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.467  -3.556   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8                                                            
CONECT   10    6   11   22                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16   19                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20   13   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22    8   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

Download
3D PDB for NP0351300 (Scleroderolide)
Download
SMILES for NP0351300 (Scleroderolide)
CC1OC2=C(C(O)=C3C(=O)C(=O)OC4=C(O)C=C(C)C2=C34)C1(C)C
Download
INCHI for NP0351300 (Scleroderolide)
InChI=1/C18H16O6/c1-6-5-8(19)15-10-9(6)16-12(18(3,4)7(2)23-16)13(20)11(10)14(21)17(22)24-15/h5,7,19-20H,1-4H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H16O6
Average Mass328.3200 Da
Monoisotopic Mass328.09469 Da
IUPAC Name6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(15),5,7,9(16),10(14)-pentaene-2,3-dione
Traditional Name6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(15),5,7,9(16),10(14)-pentaene-2,3-dione
CAS Registry NumberNot Available
SMILES
CC1OC2=C(C(O)=C3C(=O)C(=O)OC4=C(O)C=C(C)C2=C34)C1(C)C
InChI Identifier
InChI=1/C18H16O6/c1-6-5-8(19)15-10-9(6)16-12(18(3,4)7(2)23-16)13(20)11(10)14(21)17(22)24-15/h5,7,19-20H,1-4H3
InChI KeyMYDJDVOVZVSVIE-UHFFFAOYNA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 401 MHz, CDCl3, experimental)maihieu@snu.ac.krSeoul National UniversityVan-Hieu, MAI2025-07-08View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)maihieu@snu.ac.krSeoul National UniversityVan-Hieu, MAI2025-07-08View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Penicillium sp. CNUFC-EML-48 
      Not Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.79ChemAxon
pKa (Strongest Acidic)8.38ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.26 m³·mol⁻¹ChemAxon
Polarizability33.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Intaraudom C, Nitthithanasilp S, Rachtawee P, Boonruangprapa T, Prabpai S, Kongsaeree P, Pittayakhajonwut P: Phenalenone derivatives and the unusual tricyclic sesterterpene acid from the marine fungus Lophiostoma bipolare BCC25910. Phytochemistry. 2015 Dec;120:19-27. doi: 10.1016/j.phytochem.2015.11.003. Epub 2015 Nov 12. [PubMed:26582262  ] 
  2. Li Q, Zhu R, Yi W, Chai W, Zhang Z, Lian XY: Peniciphenalenins A-F from the culture of a marine-associated fungus Penicillium sp. ZZ901. Phytochemistry. 2018 Aug;152:53-60. doi: 10.1016/j.phytochem.2018.04.021. Epub 2018 May 4. [PubMed:29734036  ] 
  3. Yang SQ, Mandi A, Li XM, Liu H, Li X, Balazs Kiraly S, Kurtan T, Wang BG: Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370. Bioorg Chem. 2021 Jan;106:104477. doi: 10.1016/j.bioorg.2020.104477. Epub 2020  Nov 18. [PubMed:33279250  ] 
  4. Macabeo APG, Pilapil LAE, Garcia KYM, Quimque MTJ, Phukhamsakda C, Cruz AJC, Hyde KD, Stadler M: Alpha-Glucosidase- and Lipase-Inhibitory Phenalenones from a New Species of Pseudolophiostoma Originating from Thailand. Molecules. 2020 Feb 20;25(4):965. doi: 10.3390/molecules25040965. [PubMed:32093426  ] 
  5. Wang L, Feng Y, Tian J, Xiang M, Sun J, Ding J, Yin WB, Stadler M, Che Y, Liu X: Farming of a defensive fungal mutualist by an attelabid weevil. ISME J. 2015 Aug;9(8):1793-801. doi: 10.1038/ismej.2014.263. Epub 2015 Feb 6. [PubMed:25658054  ]