NAV

3-carboxamido-1,3,5(10)-estratrien-17(R)-spiro-2'(5',5'-dimethyl-6'oxo)tetrahydropyran

Identification

Generic Name
3-carboxamido-1,3,5(10)-estratrien-17(R)-spiro-2'(5',5'-dimethyl-6'oxo)tetrahydropyran
DrugBank Accession Number
DB07700
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 395.5344
Monoisotopic: 395.246043927
Chemical Formula
C25H33NO3
Synonyms
Not Available
External IDs
  • EM-1404
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAldo-keto reductase family 1 member C3Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroids and steroid derivatives. These are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Not Available
Direct Parent
Steroids and steroid derivatives
Alternative Parents
Phenanthrenes and derivatives / Naphthalenecarboxamides / Tetralins / Delta valerolactones / Oxanes / Primary carboxylic acid amides / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organopnictogen compounds
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Substituents
2-naphthalenecarboxamide / 2-naphthalenecarboxylic acid or derivatives / Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Delta valerolactone / Delta_valerolactone
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
YVAJWBACBRSVPR-NDUHRLLKSA-N
InChI
InChI=1S/C25H33NO3/c1-23(2)12-13-25(29-22(23)28)11-9-20-19-7-4-15-14-16(21(26)27)5-6-17(15)18(19)8-10-24(20,25)3/h5-6,14,18-20H,4,7-13H2,1-3H3,(H2,26,27)/t18-,19-,20+,24+,25-/m1/s1
IUPAC Name
(1R,3aS,3bR,9bS,11aS)-5',5',11a-trimethyl-6'-oxo-2,3,3a,3b,4,5,9b,10,11,11a-decahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxane]-7-carboxamide
SMILES
[H][C@@]12CC[C@@]3(CCC(C)(C)C(=O)O3)[C@@]1(C)CC[C@]1([H])C3=CC=C(C=C3CC[C@@]21[H])C(N)=O

References

General References
Not Available
PubChem Compound
11987804
PubChem Substance
99444171
ChemSpider
10160279
BindingDB
50384947
ChEMBL
CHEMBL521703
ZINC
ZINC000016051746
PDBe Ligand
E04
PDB Entries
1zq5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000163 mg/mLALOGPS
logP4.98ALOGPS
logP5.04Chemaxon
logS-6.4ALOGPS
pKa (Strongest Acidic)14.77Chemaxon
pKa (Strongest Basic)-0.26Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area69.39 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity112.62 m3·mol-1Chemaxon
Polarizability46.38 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9951
Blood Brain Barrier+0.9563
Caco-2 permeable+0.5259
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.5217
P-glycoprotein inhibitor IINon-inhibitor0.8033
Renal organic cation transporterNon-inhibitor0.8741
CYP450 2C9 substrateNon-substrate0.8157
CYP450 2D6 substrateNon-substrate0.8009
CYP450 3A4 substrateSubstrate0.7281
CYP450 1A2 substrateNon-inhibitor0.7164
CYP450 2C9 inhibitorNon-inhibitor0.6464
CYP450 2D6 inhibitorNon-inhibitor0.9179
CYP450 2C19 inhibitorNon-inhibitor0.5151
CYP450 3A4 inhibitorNon-inhibitor0.8674
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8975
Ames testNon AMES toxic0.8942
CarcinogenicityNon-carcinogens0.9054
BiodegradationNot ready biodegradable0.9759
Rat acute toxicity2.6365 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9935
hERG inhibition (predictor II)Non-inhibitor0.8515
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-2939ae1b4a3f54200c63
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-4e31000de2fd49b52b8b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-0029000000-4054f7ecd3e91d10183f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-b7d0f3a844e552cef032
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udl-2009000000-9ed2c0f661cad06de922
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fe1-1923000000-01dcc0c5443cbe7b0d2b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.8001
predicted
DeepCCS 1.0 (2019)
[M+H]+202.19566
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.10818
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Aldo-keto reductase family 1 member C3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
Gene Name
AKR1C3
Uniprot ID
P42330
Uniprot Name
Aldo-keto reductase family 1 member C3
Molecular Weight
36852.89 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:25 / Updated at June 12, 2020 16:52