7beta-O-methylrosmanol

ID: ALA1081338

Cas Number: 24703-38-6

PubChem CID: 46883406

Max Phase: Preclinical

Molecular Formula: C21H28O5

Molecular Weight: 360.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 7Beta-O-Methylrosmanol | 7beta-Methoxyrosmanol|24703-38-6|(1R,8R,9S,10S)-3,4-dihydroxy-8-methoxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6-trien-15-one|7beta-O-methylrosmanol|CHEMBL1081338|AKOS040761259

Canonical SMILES:  CO[C@@H]1c2cc(C(C)C)c(O)c(O)c2[C@@]23CCCC(C)(C)[C@@H]2[C@@H]1OC3=O

Standard InChI:  InChI=1S/C21H28O5/c1-10(2)11-9-12-13(15(23)14(11)22)21-8-6-7-20(3,4)18(21)17(16(12)25-5)26-19(21)24/h9-10,16-18,22-23H,6-8H2,1-5H3/t16-,17-,18+,21+/m1/s1

Standard InChI Key:  XNPVHIQPSAZTLC-WIRSXHRWSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    9.6486   -7.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6486   -8.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3586   -8.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3586   -6.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0728   -7.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0738   -8.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7871   -8.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4996   -8.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7849   -6.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4974   -7.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2149   -7.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2168   -6.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4952   -5.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7850   -6.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9378   -9.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5675   -9.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0695   -9.0572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0652   -6.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4781   -5.9984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7842   -7.8192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0679   -5.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4937   -4.9338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9337   -5.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6460   -6.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9341   -4.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2166   -8.6465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7799   -9.4869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9453   -8.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
 13 14  2  0
 14  9  1  0
  2  3  1  0
  3 15  1  0
  5  9  1  0
  3 16  1  0
  6  7  1  0
  6 17  1  6
  7  8  1  0
  5 18  1  1
  8 10  1  0
 18 19  2  0
  3  6  1  0
 20 18  1  0
  5  4  1  0
 14 21  1  0
  9 10  2  0
 13 22  1  0
  5  6  1  0
 12 23  1  0
 10 11  1  0
 23 24  1  0
 23 25  1  0
 20  7  1  0
 11 12  2  0
  8 26  1  1
  1  2  1  0
  7 27  1  1
 12 13  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1081338

   7beta-Methoxyrosmanol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 360.45

Molecular Weight (Monoisotopic): 360.1937

AlogP: 3.91

#Rotatable Bonds: 2

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.18

CX Basic pKa: ┄

CX LogP: 4.22

CX LogD: 4.21

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: 2.69

References

1. Marrero JG, Moujir L, Andrés LS, Montaño NP, Araujo L, Luis JG..  (2009)  Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone.,  72  (8): [PMID:19711987] [10.1021/np900047p]

2. Sadeghi Z, Masullo M, Cerulli A, Nazzaro F, Farimani MM, Piacente S..  (2021)  Terpenoid Constituents of Perovskia artemisioides Aerial Parts with Inhibitory Effects on Bacterial Biofilm Growth.,  84  (1.0): [PMID:33378620] [10.1021/acs.jnatprod.0c00832]

Source

Source(1):

• Scientific Literature