3beta,5alpha-dihydroxyergosta-7,22-diene - Compound Card

3beta,5alpha-dihydroxyergosta-7,22-diene

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3beta,5alpha-dihydroxyergosta-7,22-diene

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ergostane Steroid
Canonical Smiles O[C@H]1CC[C@]2([C@@](C1)(O)CC=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/C28H46O2/c1-18(2)19(3)7-8-20(4)23-9-10-24-22-12-16-28(30)17-21(29)11-15-27(28,6)25(22)13-14-26(23,24)5/h7-8,12,18-21,23-25,29-30H,9-11,13-17H2,1-6H3/b8-7+/t19-,20+,21-,23+,24-,25-,26+,27+,28+/m0/s1
InChIKey KKCUYJKFHVZXJO-AWKCEKCTSA-N
Formula C28H46O2
HBA 2
HBD 2
MW 414.67
Rotatable Bonds 4
TPSA 40.46
LogP 6.53
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 414.35
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma angolense Meliaceae Plantae 587577

Showing of synonyms

  • Happi GM, Wouamba SCN, et al. (2020). Ergostane-type steroids from the Cameroonian 'white tiama' Entandrophragma angolense.. Steroids,2020, 156, 108584. [View] [PubMed]
Pubchem: 5280675
Kegg Ligand: C04416
Chebi: 17938

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCCC4

Level: 0

Mol. Weight: 414.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.55
Plasma Protein Binding
84.58
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
8.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.13
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.81
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
-29.65
Rat (Acute)
3.49
Rat (Chronic Oral)
1.78
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
409.51
Hydration Free Energy
-3.9
Log(D) at pH=7.4
5.7
Log(P)
7.67
Log S
-6.38
Log(Vapor Pressure)
-7.8
Melting Point
163.71
pKa Acid
11.32
pKa Basic
7.36
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 0.9094
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8972
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8922
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8762
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8613
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8551
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8496
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8437
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8366
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8366
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8213
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7975
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7971
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7946
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7770
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7746
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7677
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7633
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.7496
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.7464
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7425
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7397
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7242
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7181
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7145
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7141
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7055
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7031

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