NP-MRD: Showing NP-Card for 5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol (NP0328722)

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Record Information

Version

2.0

Created at

2022-09-12 12:27:28 UTC

Updated at

2022-09-12 12:27:28 UTC

NP-MRD ID

NP0328722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol

Description

Moracin O belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol is found in Morus alba, Morus cathayana and Morus nigra. 5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol was first documented in 2015 (PMID: 25401999). Based on a literature review a significant number of articles have been published on Moracin O (PMID: 31288489) (PMID: 34946724) (PMID: 27974159) (PMID: 34047126) (PMID: 33173971) (PMID: 28208727).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122214272D          

 24 27  0  0  1  0            999 V2000
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4468   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  2  1  6  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  2  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  7 23  2  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
M  END


  Mrv1652309122214272D          

 24 27  0  0  1  0            999 V2000
   -0.9962   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4468   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0968   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8593   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  2  1  6  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  2  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  7 23  2  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1CC2=C(O1)C=C1OC(=CC1=C2)C1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O5/c1-19(2,22)18-7-11-3-10-6-15(23-16(10)9-17(11)24-18)12-4-13(20)8-14(21)5-12/h3-6,8-9,18,20-22H,7H2,1-2H3/t18-/m0/s1

> <INCHI_KEY>
HMTMYIWMPJSCAZ-SFHVURJKSA-N

> <FORMULA>
C19H18O5

> <MOLECULAR_WEIGHT>
326.348

> <EXACT_MASS>
326.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.77166673269675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(11S)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0^{3,7}]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol

> <JCHEM_LOGP>
3.0414990506666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.272400464245948

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.816928008199213

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8640608798958405

> <JCHEM_POLAR_SURFACE_AREA>
83.06

> <JCHEM_REFRACTIVITY>
88.6669

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(11S)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0^{3,7}]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.320  -2.843   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.320   0.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.722  -0.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.627  -1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.167  -1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.937   0.031   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.477   0.031   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.247   1.365   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.247  -1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.477  -2.637   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.247  -3.970   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.937  -2.637   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.722  -2.549   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   11   21                                                       
CONECT   21   20    9   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    7   24                                                  
CONECT   24   23    5                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈O₅

Average Mass

326.3480 Da

Monoisotopic Mass

326.11542 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1CC2=C(O1)C=C1OC(=CC1=C2)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C19H18O5/c1-19(2,22)18-7-11-3-10-6-15(23-16(10)9-17(11)24-18)12-4-13(20)8-14(21)5-12/h3-6,8-9,18,20-22H,7H2,1-2H3/t18-/m0/s1

InChI Key

HMTMYIWMPJSCAZ-SFHVURJKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Morus alba	LOTUS Database	35616633
Morus cathayana	LOTUS Database	35616633
Morus nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
2-phenylbenzofuran
Phenylbenzofuran
Benzofuran
Coumaran
Resorcinol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Tertiary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037512

Chemspider ID

113610304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42603436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zoofishan Z, Kusz N, Csorba A, Toth G, Hajagos-Toth J, Kothencz A, Gaspar R, Hunyadi A: Antispasmodic Activity of Prenylated Phenolic Compounds from the Root Bark of Morus nigra. Molecules. 2019 Jul 8;24(13). pii: molecules24132497. doi: 10.3390/molecules24132497. [PubMed:31288489 ]
Ko W, Liu Z, Kim KW, Dong L, Lee H, Kim NY, Lee DS, Woo ER: Kuwanon T and Sanggenon a Isolated from Morus alba Exert Anti-Inflammatory Effects by Regulating NF-kappaB and HO-1/Nrf2 Signaling Pathways in BV2 and RAW264.7 Cells. Molecules. 2021 Dec 16;26(24). pii: molecules26247642. doi: 10.3390/molecules26247642. [PubMed:34946724 ]
Zheng XK, Cao YG, Ke YY, Zhang YL, Li F, Gong JH, Zhao X, Kuang HX, Feng WS: Phenolic constituents from the root bark of Morus alba L. and their cardioprotective activity in vitro. Phytochemistry. 2017 Mar;135:128-134. doi: 10.1016/j.phytochem.2016.12.006. Epub 2016 Dec 11. [PubMed:27974159 ]
Zheng TB, Wan JQ, Yang CY, Wei Y, Wen CW, Ouyang Z: [Systematic analysis on chemical constituents of Mori Cortex, mulberry root bark and its phellem layer based on HPLC-ESI-MS]. Zhongguo Zhong Yao Za Zhi. 2021 May;46(9):2237-2244. doi: 10.19540/j.cnki.cjcmm.20200818.202. [PubMed:34047126 ]
Hardianti B, Umeyama L, Li F, Yokoyama S, Hayakawa Y: Anti‑inflammatory compounds moracin O and P from Morus alba Linn. (Sohakuhi) target the NF‑kappaB pathway. Mol Med Rep. 2020 Dec;22(6):5385-5391. doi: 10.3892/mmr.2020.11615. Epub 2020 Oct 20. [PubMed:33173971 ]
Wang YN, Liu MF, Hou WZ, Xu RM, Gao J, Lu AQ, Xie MP, Li L, Zhang JJ, Peng Y, Ma LL, Wang XL, Shi JG, Wang SJ: Bioactive Benzofuran Derivatives from Cortex Mori Radicis, and Their Neuroprotective and Analgesic Activities Mediated by mGluR(1). Molecules. 2017 Feb 8;22(2):236. doi: 10.3390/molecules22020236. [PubMed:28208727 ]
Park JH, Jung YJ, Jung JW, Shrestha S, Han D, Lim DW, Baek NI: Two new isoarylbenzofuran diglucosides from the root bark of Morus alba. J Asian Nat Prod Res. 2015;17(4):357-63. doi: 10.1080/10286020.2014.971775. Epub 2014 Nov 17. [PubMed:25401999 ]
LOTUS database [Link]

Showing NP-Card for 5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol (NP0328722)

MOL for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

3D MOL for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

3D SDF for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

3D-SDF for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

PDB for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

3D PDB for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

SMILES for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

INCHI for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

Structure for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)

3D Structure for NP0328722 (5-[(11s)-11-(2-hydroxypropan-2-yl)-4,12-dioxatricyclo[7.3.0.0³,⁷]dodeca-1(9),2,5,7-tetraen-5-yl]benzene-1,3-diol)