NP-MRD: Showing NP-Card for Tephrosin (NP0051492)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:50:16 UTC

Updated at

2024-09-03 04:22:36 UTC

NP-MRD ID

NP0051492

Natural Product DOI

https://doi.org/10.57994/2913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tephrosin

Description

Tephrosin, also known as deguelinol I or hydroxydeguelin, belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Thus, tephrosin is considered to be a flavonoid. Tephrosin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Tephrosin is found in Amorpha fruticosa, Antheroporum pierrei, Crotalaria spp., Derris elliptica, Derris malaccensis, Derris oblonga, Derris trifoliata , Erycibe expansa , Lonchocarpus longifolius, Lonchocarpus spp., Lonchocarpus spruceanus, Lonchocarpus utilis, Milletia dura, Millettia dura, Millettia ferruginea , Millettia oblata ssp. teitensis , Millettia pachycarpa, Millettia taiwaniana, Mundulea sericea , Piscidia mollois, Sarcolobus globosus, Tephrosia candida, Tephrosia elata , Tephrosia leiocarpa, Tephrosia purpurea, Tephrosia spp. and Tephrosia vogelii. Tephrosin was first documented in 2020 (PMID: 33096762). Based on a literature review a significant number of articles have been published on tephrosin (PMID: 33776066) (PMID: 35219716) (PMID: 34564803) (PMID: 33391424) (PMID: 38579352).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200502D          

 30 34  0  0  1  0            999 V2000
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2179    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2179    0.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  5 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  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
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  1  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -6.4372   -2.5905    1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3452   -1.3274    0.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1054   -0.7777    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9533   -1.4314    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7062   -0.9043    0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853    0.3289    0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7149    1.0219   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623    0.4707   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220    1.1322   -0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9889    2.3870   -1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2188    0.8589   -0.1409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1937    2.1817   -0.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814    0.0763   -1.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -0.4579   -2.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8579   -0.0665   -1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5254   -0.6860   -2.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8980   -0.8228   -2.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210   -0.3223   -1.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9756    0.2895   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995    0.4195   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120    1.0369    0.8696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329    0.6329    1.1110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3913   -0.8165    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250   -1.5333    1.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7609    0.7926    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0606    0.6610    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7710    0.0116   -0.1722 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5570   -1.2115    0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000    1.0280   -0.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9746   -0.4575   -1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7444   -3.3020    0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4937   -2.9375    1.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2256   -2.5368    2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0023   -2.4164    1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5963    2.0029   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5794    2.2614   -2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0096    2.8218   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3541    3.0733   -0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755    2.7912    0.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9424   -1.0630   -3.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016   -1.3060   -3.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8577    1.2317    1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953   -1.3407    1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214   -0.9255    2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559    1.2906    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6257    1.0501    1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8583   -1.9530    0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3236   -0.9033    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0561   -1.6404   -0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4114    2.0699   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7187    0.9172   -0.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9599    0.8905   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  6
 11 22  1  0
 22 23  1  0
 23 24  1  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 27 30  1  0
 30 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  2  0
  8  3  1  0
 13 11  1  0
 24  5  1  0
 15 20  1  0
 18 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  7 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 22 42  1  1
 23 43  1  0
 23 44  1  0
 25 45  1  0
 26 46  1  0
 28 47  1  0
 28 48  1  0
 28 49  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 17 41  1  0
 16 40  1  0
M  END


  Mrv1652304282200502D          

 30 34  0  0  1  0            999 V2000
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2179    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2179    0.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  5 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  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
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 14 29  1  0  0  0  0
 15 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@@]1(O)[C@@H](CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1

> <INCHI_KEY>
AQBZCCQCDWNNJQ-AUSIDOKSSA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.422

> <EXACT_MASS>
410.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.81566525053669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,14R)-14-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.7126881476666673

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.072497074074052

> <JCHEM_PKA_STRONGEST_BASIC>
-4.21120444577967

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
108.46399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,14R)-14-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.344   2.104   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.473   0.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.473   1.493   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.644   2.104   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16   18   30                                             
CONECT   16   15    4   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19   23                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   21   27                                                       
CONECT   27   26                                                            
CONECT   28   19   29                                                       
CONECT   29   28   14                                                       
CONECT   30   15                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(7AR,13ar)-13,13a-dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7ah)-one	ChEBI
Deguelinol I	ChEBI
Hydroxydeguelin	ChEBI

Chemical Formula

C₂₃H₂₂O₇

Average Mass

410.4220 Da

Monoisotopic Mass

410.13655 Da

IUPAC Name

(1R,14R)-14-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

Traditional Name

(1R,14R)-14-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@@]1(O)[C@@H](CO2)OC2=C3C=CC(C)(C)OC3=CC=C2C1=O

InChI Identifier

InChI=1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1

InChI Key

AQBZCCQCDWNNJQ-AUSIDOKSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Uppsala University	Mate Erdelyi	2024-06-22	View Spectrum

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
Amorpha fruticosa	Plant	KNApSAcK
Antheroporum pierrei	LOTUS Database	35616633
Crotalaria spp.	Plant	KNApSAcK
Derris elliptica	LOTUS Database	35616633
Derris malaccensis	Plant	KNApSAcK
Derris oblonga	Plant	KNApSAcK
Derris trifoliata	Plant	KNApSAcK
Erycibe expansa	Plant	KNApSAcK
Lonchocarpus longifolius	Plant	KNApSAcK
Lonchocarpus spp.	Plant	KNApSAcK
Lonchocarpus spruceanus	Plant	KNApSAcK
Lonchocarpus utilis	LOTUS Database	35616633
Milletia dura	-	KNApSAcK
Millettia dura	Plant	KNApSAcK
Millettia ferruginea	Plant	KNApSAcK
Millettia oblata ssp. teitensis		Not Available
Millettia oblata ssp. teitensis	Plant	KNApSAcK
Millettia pachycarpa	LOTUS Database	35616633
Millettia taiwaniana	Plant	KNApSAcK
Mundulea sericea	Plant	KNApSAcK
Piscidia mollois	Plant	KNApSAcK
Sarcolobus globosus	LOTUS Database	35616633
Tephrosia candida	LOTUS Database	35616633
Tephrosia elata	Plant	KNApSAcK
Tephrosia leiocarpa	LOTUS Database	35616633
Tephrosia purpurea	LOTUS Database	35616633
Tephrosia spp.	Plant	KNApSAcK
Tephrosia vogelii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

Rotenone or derivatives
8-prenylated isoflavanone
Isoflavanone
Isoflavan
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:9442 )
aromatic ether (CHEBI:9442 )
organic heteropentacyclic compound (CHEBI:9442 )
rotenones (CHEBI:9442 )
rotenones (C10535 )
Rotenoid flavonoids (C10535 )
Rotenoid flavonoids (LMPK12060047 )

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	2.66	ALOGPS
logP	2.71	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	11.07	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.46 m³·mol⁻¹	ChemAxon
Polarizability	42.82 Å³	ChemAxon
Number of Rings	5	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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Tephrosin

METLIN ID

Not Available

PubChem Compound

114909

PDB ID

Not Available

ChEBI ID

9442

Good Scents ID

Not Available

References

General References

Redman ZC, Brodnax K, Couture J, Tomco PL: Identification of Rotenone and Five Rotenoids in CFT Legumine Piscicide Formulation via High Resolution Mass Spectrometry and a New High-Throughput Extraction Procedure. Chromatographia. 2021 Feb;84(2):207-214. doi: 10.1007/s10337-020-03987-9. Epub 2020 Nov 21. [PubMed:33776066 ]
Chepkirui C, Bourgard C, Gilissen PJ, Ndakala A, Derese S, Gutlin Y, Erdelyi M, Yenesew A: A new beta-hydroxydihydrochalcone from Tephrosia uniflora, and the revision of three beta-hydroxydihydrochalcones to flavanones. Fitoterapia. 2022 Apr;158:105166. doi: 10.1016/j.fitote.2022.105166. Epub 2022 Feb 25. [PubMed:35219716 ]
Darzi S, Mirzaei SA, Elahian F, Peymani A, Rahmani B, Pishkhan Dibazar S, Shirian S, Shakeri Chaleshtori L, Aali E: Improvement of cytotoxicity of mitoxantrone and daunorubicin by candidone, tephrosin, and bavachinin. Mol Biol Rep. 2021 Nov;48(11):7105-7111. doi: 10.1007/s11033-021-06700-7. Epub 2021 Sep 25. [PubMed:34564803 ]
Du J, Jiang F, Xu SS, Huang ZF, Chen LL, Li L: Tephrosin induces apoptosis of human pancreatic cancer cells through the generation of reactive oxygen species. J Cancer. 2021 Jan 1;12(1):270-280. doi: 10.7150/jca.50360. eCollection 2021. [PubMed:33391424 ]
Zhang P, Qin D, Chen J, Zhang Z: Plants in the Genus Tephrosia: Valuable Resources for Botanical Insecticides. Insects. 2020 Oct 21;11(10). pii: insects11100721. doi: 10.3390/insects11100721. [PubMed:33096762 ]
Kiganda I, Bogaerts J, Wieske LHE, Deyou T, Atilaw Y, Uwamariya C, Miah M, Said J, Ndakala A, Akala HM, Herrebout W, Trybala E, Bergstrom T, Yenesew A, Erdelyi M: Antiviral Rotenoids and Isoflavones Isolated from Millettia oblata ssp. teitensis. J Nat Prod. 2024 Apr 26;87(4):1003-1012. doi: 10.1021/acs.jnatprod.3c01288. Epub 2024 Apr 5. [PubMed:38579352 ]
DOI: 10.1021/acs.jnatprod.3c01288
PMID: 38579352

Showing NP-Card for Tephrosin (NP0051492)

MOL for NP0051492 (Tephrosin)

3D MOL for NP0051492 (Tephrosin)

3D SDF for NP0051492 (Tephrosin)

3D-SDF for NP0051492 (Tephrosin)

PDB for NP0051492 (Tephrosin)

3D PDB for NP0051492 (Tephrosin)

SMILES for NP0051492 (Tephrosin)

INCHI for NP0051492 (Tephrosin)

Structure for NP0051492 (Tephrosin)

3D Structure for NP0051492 (Tephrosin)