Neocyclocitrinol C

ID: ALA524981

PubChem CID: 44587549

Max Phase: Preclinical

Molecular Formula: C25H36O4

Molecular Weight: 400.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Neocyclocitrinol C | Neocyclocitrinol C|CHEMBL524981|CHEBI:215336|(2R,5R,6R,9R,13S,15S)-6-[(E,4R,5S)-4,5-dihydroxyhex-2-en-2-yl]-15-hydroxy-5-methyltetracyclo[11.4.1.02,10.05,9]octadeca-1(17),10-dien-12-one

Canonical SMILES:  C/C(=C\[C@@H](O)[C@H](C)O)[C@H]1CC[C@H]2C3=CC(=O)[C@H]4CC(=CC[C@H](O)C4)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C25H36O4/c1-14(10-23(28)15(2)26)21-6-7-22-20-13-24(29)17-11-16(4-5-18(27)12-17)19(20)8-9-25(21,22)3/h4,10,13,15,17-19,21-23,26-28H,5-9,11-12H2,1-3H3/b14-10+/t15-,17-,18-,19+,21+,22-,23+,25+/m0/s1

Standard InChI Key:  HDGOYEAHQQCXLC-BFHGYSRFSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    7.6887   -8.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3030   -9.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9139   -9.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7394   -9.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2861   -8.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8653   -8.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3885   -9.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1397   -9.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0949  -10.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6954  -10.1353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0229  -10.6605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4588   -8.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1751   -8.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1653   -6.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4512   -7.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8775   -7.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8787   -8.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6633   -8.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1511   -7.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6640   -6.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9652   -6.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9312   -6.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9642   -8.8919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7752   -7.6068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0448  -10.6661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7397   -6.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3858   -5.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0028   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8113   -5.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3568   -5.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4572   -4.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0742   -4.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
  1  8  1  0
  7  9  1  0
  8  3  1  0
  9  3  1  0
  7 10  1  1
  3 11  1  1
 12 13  1  0
 12 15  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 16 21  1  1
 20 22  1  1
 17 23  1  6
 12 24  1  6
  4 25  2  0
 22 26  2  0
  1 12  1  0
 22 27  1  0
 13  2  2  0
 26 28  1  0
  2  4  1  0
 28 29  1  0
  3  4  1  0
 29 30  1  0
  5  6  1  0
 28 31  1  1
  6  1  2  0
 29 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA524981

   NEOCYCLOCITRINOL C

Molecule Features

Natural Product: No

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: 400.56

Molecular Weight (Monoisotopic): 400.2614

AlogP: 3.71

#Rotatable Bonds: 3

Polar Surface Area: 77.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.73

CX Basic pKa: ┄

CX LogP: 2.77

CX LogD: 2.77

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: 3.15

References

1. Du L, Zhu T, Fang Y, Gu Q, Zhu W..  (2008)  Unusual C25 steroid isomers with bicyclo[4.4.1]A/B rings from a volcano ash-derived fungus Penicillium citrinum.,  71  (8): [PMID:18656987] [10.1021/np8000442]

2. He ZH, Xie CL, Wu T, Yue YT, Wang CF, Xu L, Xie MM, Zhang Y, Hao YJ, Xu R, Yang XW..  (2023)  Tetracyclic Steroids Bearing a Bicyclo[4.4.1] Ring System as Potent Antiosteoporosis Agents from the Deep-Sea-Derived Fungus Rhizopus sp. W23.,  86  (1.0): [PMID:36547402] [10.1021/acs.jnatprod.2c00866]

Source

Source(1):

• Scientific Literature