threo-23-O-Methylneocyclocitrinol

Names and Identifiers

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

Standard InChI: InChI=1S/C26H38O4/c1-15(11-25(30-4)16(2)27)22-7-8-23-21-14-24(29)18-12-17(5-6-19(28)13-18)20(21)9-10-26(22,23)3/h5,11,14,16,18-20,22-23,25,27-28H,6-10,12-13H2,1-4H3/b15-11+/t16-,18+,19+,20-,22-,23+,25-,26-/m1/s1

Standard InChI Key: KJZPRGNCDGAUNA-WZEAMOGMSA-N

Molfile:

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.0928  -17.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4771  -18.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8684  -18.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0431  -18.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4920  -17.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149  -17.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3911  -18.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431  -17.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836  -18.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0825  -18.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573  -19.4812    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223  -16.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6041  -17.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149  -15.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3296  -16.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070  -16.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053  -16.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1170  -17.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676  -16.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1201  -15.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160  -15.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472  -15.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8175  -17.7111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0036  -16.4273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349  -19.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550  -14.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957  -14.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199  -14.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0277  -13.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729  -13.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378  -12.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2898  -13.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735  -14.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  2  2  0
  2  4  1  0
  3  4  1  0
  5  6  1  0
  6  1  2  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
 22 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  1
 30 31  1  0
 29 32  1  6
  1 12  1  0
 29 33  1  0
M  END

Alternative Forms

Parent:

ALA456770
(2R,5R,6R,9R,13S,15S)-15-hydroxy-6-[(E,4R,5R)-5-hydroxy-4-methoxyhex-2-en-2-yl]-5-methyltetracyclo[11.4.1.02,10.05,9]octadeca-1(17),10-dien-12-one

Associated Targets(Human)

GPR12 Tbio G-protein coupled receptor 12 (6 Activities)

Discover Target: GPR12

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

CHO (4503 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 414.59	Molecular Weight (Monoisotopic): 414.2770	AlogP: 4.37	#Rotatable Bonds: 4
Polar Surface Area: 66.76	Molecular Species: NEUTRAL	HBA: 4	HBD: 2
#RO5 Violations: ┄	HBA (Lipinski): 4	HBD (Lipinski): 2	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: ┄	CX Basic pKa: ┄	CX LogP: 3.41	CX LogD: 3.41
Aromatic Rings: ┄	Heavy Atoms: 30	QED Weighted: 0.67	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]

Source

Source(1):

Scientific Literature