Daphneodorin D; 12-O-(E)-coumaroyl-9,13,14-ortho-(2E,4E)-decadienylidyne-5beta,12beta-dihydroxyresiniferonol-6alpha,7alpha-oxide

ID: ALA4797613

PubChem CID: 162674597

Max Phase: Preclinical

Molecular Formula: C39H46O11

Molecular Weight: 690.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@]12O[C@@]3(/C=C/C=C/CCCCC)O[C@@H]1[C@@H]1[C@@H]4O[C@]4(CO)[C@@H](O)[C@]4(O)C(=O)C(C)=C[C@H]4[C@@]1(O3)[C@H](C)[C@H]2OC(=O)/C=C/c1ccc(O)cc1

Standard InChI:  InChI=1S/C39H46O11/c1-6-7-8-9-10-11-12-19-36-48-33-29-32-35(21-40,47-32)34(44)37(45)27(20-23(4)30(37)43)39(29,50-36)24(5)31(38(33,49-36)22(2)3)46-28(42)18-15-25-13-16-26(41)17-14-25/h10-20,24,27,29,31-34,40-41,44-45H,2,6-9,21H2,1,3-5H3/b11-10+,18-15+,19-12+/t24-,27-,29+,31-,32+,33-,34-,35+,36-,37-,38+,39+/m1/s1

Standard InChI Key:  HTAUZCYAAWBILH-OTSBJUMTSA-N

Molfile:  

 
     RDKit          2D

 54 60  0  0  0  0  0  0  0  0999 V2000
    4.9774   -7.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580   -6.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3385   -7.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3384   -7.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0918   -8.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5563   -7.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0919   -6.9245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767   -7.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580   -8.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4716   -9.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0191   -9.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2446   -8.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -7.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9622   -8.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2275   -9.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7874   -9.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2595   -9.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285   -9.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7806   -9.6819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2077   -8.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0867  -10.3478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6196   -9.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -7.4868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2540  -10.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683  -10.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0930   -8.9066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6543   -7.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -6.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3006   -6.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9803   -5.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3735   -7.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7820   -8.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5992   -8.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0077   -8.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8249   -8.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2333   -9.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0505   -9.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4590  -10.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2762  -10.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682   -6.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3312   -8.7745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6036   -9.1253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2416   -6.0588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6453   -5.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2319   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625   -5.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4147   -4.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0013   -3.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083   -3.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9956   -2.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1775   -2.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7740   -3.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891   -3.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631   -1.8337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0
  1  2  1  0
  9  4  1  0
  3  2  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  8  9  1  0
  9 16  1  0
  8 12  1  0
 17 10  1  0
 11 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 17 16  1  0
 17 18  1  0
 16 18  1  0
 15 19  2  0
 14 20  1  0
 10 21  1  1
 11 22  1  1
 12 23  1  6
 17 24  1  1
 24 25  1  0
  9 26  1  1
  8 27  1  6
  6 27  1  0
  3 28  1  1
 28 29  1  0
 28 30  2  0
  6 31  1  6
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
  1 40  1  6
  4 41  1  1
 16 42  1  1
  2 43  1  1
 43 44  1  0
 44 45  1  0
 44 46  2  0
 45 47  2  0
 47 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  2  0
 51 52  1  0
 52 53  2  0
 53 48  1  0
 51 54  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4797613

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 690.79

Molecular Weight (Monoisotopic): 690.3040

AlogP: 3.81

#Rotatable Bonds: 11

Polar Surface Area: 164.51

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.40

CX Basic pKa: ┄

CX LogP: 5.73

CX LogD: 5.73

Aromatic Rings: 1

Heavy Atoms: 50

QED Weighted: 0.07

Np Likeness Score: 3.28

References

1. Otsuki K,Li W,Miura K,Asada Y,Huang L,Chen CH,Lee KH,Koike K.  (2020)  Isolation, Structural Elucidation, and Anti-HIV Activity of Daphnane Diterpenoids from Daphne odora.,  83  (11): [PMID:32997496] [10.1021/acs.jnatprod.0c00540]

Source

Source(1):

• Scientific Literature