Lupulin A - Compound Card

Lupulin A

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Lupulin A

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Clerodane Diterpenoid
Canonical Smiles CO[C@@H]1C[C@H]2[C@@H](O1)O[C@@H](C2)[C@@]1(C)[C@H](C)C[C@@H]([C@@]2([C@@H]1C[C@@H](O)[C@@H]([C@@]12CO1)OC(=O)[C@@H](CC)C)COC(=O)C)OC(=O)C
InChI InChI=1S/C30H46O11/c1-8-15(2)26(34)41-25-20(33)12-21-28(6,22-10-19-11-24(35-7)40-27(19)39-22)16(3)9-23(38-18(5)32)29(21,13-36-17(4)31)30(25)14-37-30/h15-16,19-25,27,33H,8-14H2,1-7H3/t15-,16-,19+,20-,21-,22+,23+,24+,25+,27-,28+,29+,30-/m1/s1
InChIKey UEZOFWAZJUOMCN-BVDQYQNCSA-N
Formula C30H46O11
HBA 11
HBD 1
MW 582.69
Rotatable Bonds 8
TPSA 139.35
LogP 2.75
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 582.3
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ajuga pseudoiva Lamiaceae Plantae 2026104
2 Ajuga pseudoiva Lamiaceae Plantae 2026104

Showing of synonyms

  • Ben Jannet H, Chaari A, et al. (1999). Neo-clerodane diterpenoids from Ajuga pseudoiva leaves. Phytochemistry,1999,52(8),1541-1545. [View]
  • Ben Jannet H, Harzallah-Skhiri F, et al. (2000). Responses of Spodoptera littoralis larvae to Tunisian plant extracts and to neo-clerodane diterpenoids isolated from Ajuga pseudoiva leaves. Fitoterapia,2000,71(2),105-112. [View] [PubMed]
Pubchem: 44566822
Nmrshiftdb2: 70060934

No compound-protein relationship available.

Structure

SMILES: O1CC12C3C(CCC2)C(CCC3)C(C4)OC(C45)OCC5

Level: 1

Mol. Weight: 582.69 g/mol

Structure

SMILES: O1CC12C3C(CCC2)CCCC3

Level: 0

Mol. Weight: 582.69 g/mol

Structure

SMILES: C1COC(C12)OCC2

Level: 0

Mol. Weight: 582.69 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.370
Plasma Protein Binding
54.58
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
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.150
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.330
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.420
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.100
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
-5805.690
Rat (Acute)
5.460
Rat (Chronic Oral)
2.070
Fathead Minnow
16.620
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
354.060
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.230
Log(P)
2.35
Log S
-4.72
Log(Vapor Pressure)
-9.64
Melting Point
107.14
pKa Acid
5.73
pKa Basic
1.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9631
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9631
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8181
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8181
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8031
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8031
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7865
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7865
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7739
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7738
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7738
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7594
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7594
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7236
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7236
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7209
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7209
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7083
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7083
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7065
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7065

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