(7R,10S)‐10‐hydroxy-sydowic acid - Compound Card

(7R,10S)‐10‐hydroxy-sydowic acid

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(7R,10S)‐10‐hydroxy-sydowic acid

Structure
Zoomed Structure
  • Family: Trichocomaceae
  • Kingdom: Fungi
  • Class: Terpenoid
    • Subclass: Meroterpenoid
Canonical Smiles Oc1cc(ccc1[C@@]1(C)CC[C@@H](O1)C(O)(C)C)C(=O)O
InChI InChI=1S/C15H20O5/c1-14(2,19)12-6-7-15(3,20-12)10-5-4-9(13(17)18)8-11(10)16/h4-5,8,12,16,19H,6-7H2,1-3H3,(H,17,18)/t12-,15-/m1/s1
InChIKey QIBHUHQNTPBVNF-IUODEOHRSA-N
Formula C15H20O5
HBA 4
HBD 3
MW 280.32
Rotatable Bonds 3
TPSA 86.99
LogP 2.26
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 280.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Elsbaey M, Tanaka C, et al. (2019). New secondary metabolites from the mangrove endophytic fungus Aspergillus versicolor. Phytochemistry Letters,2019,32,70-76. [View]
Pubchem: 139588049
Nmrshiftdb2: 70011513

No compound-protein relationship available.

Structure

SMILES: O1CCCC1c2ccccc2

Level: 1

Mol. Weight: 148.2 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 72.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.1
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.420
Plasma Protein Binding
64.68
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
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.710
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.190
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.740
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.810
Micronucleos
Toxic
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
-0.890
Rat (Acute)
2.200
Rat (Chronic Oral)
2.570
Fathead Minnow
3.910
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
332.940
Hydration Free Energy
-10.470
Log(D) at pH=7.4
-0.350
Log(P)
2.05
Log S
-2.65
Log(Vapor Pressure)
-6.88
Melting Point
192.19
pKa Acid
5.4
pKa Basic
6.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9247
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9075
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8953
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8572
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8409
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8372
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8298
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8062
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8037
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8020
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7954
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7925
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7908
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7884
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7850
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7822
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.7815
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7797
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7796
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7681
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 4 0.7641
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7572
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7503
Uncharacterized PhzA/B-like protein PA3332 Q9HYR3 Y3332_PSEAE Pseudomonas aeruginosa 4 0.7461
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7430
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7395
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7368
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7356
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7254
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7177
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7166
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 2 0.7063
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7046
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7023

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