2alpha,3beta-dihydroxylupan-29-oic acid - Compound Card

2alpha,3beta-dihydroxylupan-29-oic acid

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2alpha,3beta-dihydroxylupan-29-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles OC(=O)[C@@H]([C@@H]1CC[C@]2(C1C1CCC3[C@@]([C@]1(C)CC2)(C)CCC1[C@]3(C)C[C@@H](O)[C@@H](C1(C)C)O)C)C
InChI InChI=1S/C30H50O4/c1-17(25(33)34)18-10-12-27(4)14-15-29(6)19(23(18)27)8-9-22-28(5)16-20(31)24(32)26(2,3)21(28)11-13-30(22,29)7/h17-24,31-32H,8-16H2,1-7H3,(H,33,34)/t17-,18+,19?,20-,21?,22?,23?,24+,27-,28+,29-,30-/m1/s1
InChIKey HZHRTQONQJYMCR-JRJFFISUSA-N
Formula C30H50O4
HBA 3
HBD 3
MW 474.73
Rotatable Bonds 2
TPSA 77.76
LogP 6.14
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.97
Exact Mass 474.37
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Cassia arereh Leguminosae/Fabaceae Plantae 1977549

Showing of synonyms

  • Missi MB, Evina JN, et al. (2022). Antibacterial and cytotoxic activities of undescribed cassiaric acid and other constituents from Cassia arereh stem barks.. Natural product research,2022, 36(17), 4330-4339. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 474.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.42
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.690
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.640
Plasma Protein Binding
83.59
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
3.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.140
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.800
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.100
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
Safe
T. Pyriformis
-150.430
Rat (Acute)
2.440
Rat (Chronic Oral)
2.400
Fathead Minnow
3.980
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
463.840
Hydration Free Energy
-2.460
Log(D) at pH=7.4
4.820
Log(P)
6.22
Log S
-5.88
Log(Vapor Pressure)
-9.58
Melting Point
272.25
pKa Acid
5.12
pKa Basic
8.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8569
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8457
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7865
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7863
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7701
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7331
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7185
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7094
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7081
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7080
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7031
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7006

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