Desmosterol - Compound Card

Desmosterol

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Desmosterol

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCC=C(C)C)C)C)C1)C
InChI InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey AVSXSVCZWQODGV-DPAQBDIFSA-N
Formula C27H44O
HBA 1
HBD 1
MW 384.65
Rotatable Bonds 4
TPSA 20.23
LogP 7.31
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 384.34
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ecballium elaterium Cucurbitaceae Plantae 3679

Showing of synonyms

  • Touihri I, Kallech-Ziri O, et al. (2019). Ecballium elaterium (L.) A. Rich. seed oil: Chemical composition and antiproliferative effect on human colonic adenocarcinoma and fibrosarcoma cancer cell lines. Arabian Journal of Chemistry, 2019, 12(8), 2347-2355. [View]
Pubchem: 439577
Kegg Ligand: C01802
Chebi: 17737
Nmrshiftdb2: 60018482
Metabolights: MTBLC17737
Pdb Ligand: MHQ
Bindingdb: 50280402
CPRiL: 1383
Structure

SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4

Level: 0

Mol. Weight: 384.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.59
Plasma Protein Binding
78.71
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
10.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.96
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.11
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-13.48
Rat (Acute)
1.96
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
Safe
SR-p53
Safe

General Properties

Boiling Point
393.65
Hydration Free Energy
-3.27
Log(D) at pH=7.4
6.22
Log(P)
8.19
Log S
-6.78
Log(Vapor Pressure)
-6.84
Melting Point
137.83
pKa Acid
13.47
pKa Basic
8.62
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 0.9370
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9353
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9333
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9223
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9166
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9150
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9043
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9016
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8920
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8899
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8861
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8827
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8809
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8808
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8696
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8659
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8562
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8523
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8502
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 5 0.8435
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8394
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 5 0.8340
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8296
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8283
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8122
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7854
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7772
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 4 0.7714
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7712
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7698
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7610
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 4 0.7600
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7561
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7523
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7499
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7483
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7471
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7468
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7322
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7309
Apocarotenoid-15,15'-oxygenase P74334 ACOX_SYNY3 Synechocystis sp 5 0.7219
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7174
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7170
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7154
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7133
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7120
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7115
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7049
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7042
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7023

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