Isolophanthin A - Compound Card

Isolophanthin A

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Isolophanthin A

Structure
Zoomed Structure
  • Family: Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles O[C@H]1CC[C@]2([C@H](C1(C)C)CCc1c2ccc(c1)C(O)(C)C)C
InChI InChI=1S/C20H30O2/c1-18(2)16-9-6-13-12-14(19(3,4)22)7-8-15(13)20(16,5)11-10-17(18)21/h7-8,12,16-17,21-22H,6,9-11H2,1-5H3/t16-,17-,20+/m0/s1
InChIKey VXXSPOVQLBTGOO-ABSDTBQOSA-N
Formula C20H30O2
HBA 2
HBD 2
MW 302.46
Rotatable Bonds 1
TPSA 40.46
LogP 3.92
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 302.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Croton megalocarpoides Euphorbiaceae Plantae 1704624

Showing of synonyms

  • Ndunda B, Langat MK, et al. (2016). New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis and M. G. Gilbert.. Planta Med,2016,82(11-12),1079-1086. [View] [PubMed]
Pubchem: 53496760
Nmrshiftdb2: 60045203

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)CCC3C2CCCC3

Level: 0

Mol. Weight: 186.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.31
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
80.75
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.81
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.17
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.15
Micronucleos
Safe
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
0.16
Rat (Acute)
2.25
Rat (Chronic Oral)
2.01
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
349.52
Hydration Free Energy
-6.06
Log(D) at pH=7.4
3.44
Log(P)
4.13
Log S
-4.25
Log(Vapor Pressure)
-6.1
Melting Point
144.37
pKa Acid
12.89
pKa Basic
7.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8670
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8670
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8572
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8572
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8417
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8417
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8062
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8062
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7877
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7877
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7733
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7733
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7712
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7712
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7667
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7667
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7649
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7649
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7639
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7639
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7617
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7617
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7520
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7520
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7486
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7486
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7464
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7464
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7456
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7456
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7451
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7451
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7451
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7451
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7323
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7323
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7215
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7215
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7213
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7213
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7194
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7194
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7193
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7193
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7092
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7092

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