(3beta,5alpha,6beta)-3,5,6-trihydroxy-ergosta7,22-diene - Compound Card

(3beta,5alpha,6beta)-3,5,6-trihydroxy-ergosta7,22-diene

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(3beta,5alpha,6beta)-3,5,6-trihydroxy-ergosta7,22-diene

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles O[C@H]1CC[C@]2([C@@](C1)(O)[C@H](O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C(C)C)C)C)C)C
InChI InChI=1S/C28H46O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-15-25(30)28(31)16-20(29)11-14-27(28,6)24(21)12-13-26(22,23)5/h7-8,15,17-20,22-25,29-31H,9-14,16H2,1-6H3/b8-7+/t18-,19-,20+,22-,23+,24+,25-,26-,27-,28+/m1/s1
InChIKey ARXHRTZAVQOQEU-LYHJVHLQSA-N
Formula C28H46O3
HBA 3
HBD 3
MW 430.67
Rotatable Bonds 4
TPSA 60.69
LogP 5.5
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 430.34
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus terreus Trichocomaceae Fungi 33178

Showing of synonyms

  • Shaaban M, El-Metwally M.M, et al. (2018). Terretonin M: A new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins. Nat Prod Res,2018,32(20),2437-2446. [View] [PubMed]
Pubchem: 12302764
Nmrshiftdb2: 60068601

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCCC4

Level: 0

Mol. Weight: 430.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.37
Plasma Protein Binding
88.4
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
7.6
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
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
1.0
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.4
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-42.07
Rat (Acute)
3.78
Rat (Chronic Oral)
2.27
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
421.8
Hydration Free Energy
-3.7
Log(D) at pH=7.4
5.07
Log(P)
6.21
Log S
-5.74
Log(Vapor Pressure)
-8.75
Melting Point
174.33
pKa Acid
9.75
pKa Basic
6.98
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9069
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8677
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8563
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8349
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7957
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7831
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7743
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7605
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7532
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7472
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7452
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7377
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7368
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7348

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