3beta-(propyloxycarbonylamino)-dictyophlebin-16-ene [(20S)-20-(N,N-dimethylamino)-3beta-(propyloxycarbonylamino)-5alpha-pregn-16-ene - Compound Card

3beta-(propyloxycarbonylamino)-dictyophlebin-16-ene [(20S)-20-(N,N-dimethylamino)-3beta-(propyloxycarbonylamino)-5alpha-pregn-16-ene

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3beta-(propyloxycarbonylamino)-dictyophlebin-16-ene [(20S)-20-(N,N-dimethylamino)-3beta-(propyloxycarbonylamino)-5alpha-pregn-16-ene

Structure
Zoomed Structure
  • Family: Fungi - Mucoraceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Steroid Alkaloid
Canonical Smiles CCCOC(=O)N[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC=C2[C@@H](N(C)C)C)C)C
InChI InChI=1S/C27H46N2O2/c1-7-16-31-25(30)28-20-12-14-26(3)19(17-20)8-9-21-23-11-10-22(18(2)29(5)6)27(23,4)15-13-24(21)26/h10,18-21,23-24H,7-9,11-17H2,1-6H3,(H,28,30)/t18-,19-,20-,21-,23-,24-,26-,27+/m0/s1
InChIKey RGFKHIZOQUIWHN-VVKDTSJFSA-N
Formula C27H46N2O2
HBA 3
HBD 1
MW 430.68
Rotatable Bonds 5
TPSA 41.57
LogP 6.02
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 430.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Rhizopus stolonifer Mucoraceae Fungi 4846

Showing of synonyms

  • Devkota KP, Choudhary MI, et al. (2007). Microbial transformation of the steroidal alkaloid dictyophlebine by Rhizopus stolonifer.. Chemical & pharmaceutical bulletin,2007, 55(4), 682-684. [View] [PubMed]
Pubchem: 16655876

No compound-protein relationship available.

Structure

SMILES: C1=CCC(C12)C3C(CC2)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 430.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.49
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.98
Plasma Protein Binding
71.48
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.43
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.46
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.55
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-53.9
Rat (Acute)
2.91
Rat (Chronic Oral)
1.39
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
412.59
Hydration Free Energy
-3.57
Log(D) at pH=7.4
5.18
Log(P)
6.08
Log S
-5.26
Log(Vapor Pressure)
-7.46
Melting Point
135.93
pKa Acid
7.78
pKa Basic
8.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8701
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8296
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8039
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7966
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7805
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7795
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7707
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7632
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7554
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7531
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7494
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7439
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7388
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7242
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7100
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7022

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