Sarcolobine - Compound Card

Sarcolobine

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Sarcolobine

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles COc1cc2c(cc1OC)OC[C@@H]1[C@@]2(O)C(=O)c2c(O1)c1c(cc2)OC2C1C2(C)C
InChI InChI=1S/C23H22O7/c1-22(2)18-17-12(29-21(18)22)6-5-10-19(17)30-16-9-28-13-8-15(27-4)14(26-3)7-11(13)23(16,25)20(10)24/h5-8,16,18,21,25H,9H2,1-4H3/t16-,18?,21?,23-/m1/s1
InChIKey HJDODWXISWRQIF-RNPWIZMZSA-N
Formula C23H22O7
HBA 7
HBD 1
MW 410.42
Rotatable Bonds 2
TPSA 83.45
LogP 2.81
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.43
Exact Mass 410.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia vogelii Leguminosae/Fabaceae Plantae 1157238

Showing of synonyms

  • Stevenson PC, Kite GC, et al. (2012). Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment.. Phytochemistry,2012(78),135-146. [View] [PubMed]
Pubchem: 76318737

No compound-protein relationship available.

Structure

SMILES: C12C(C1)Oc3c2c4c(cc3)C(=O)C5c6c(OCC5O4)cccc6

Level: 0

Mol. Weight: 410.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.530
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.230
Plasma Protein Binding
74.61
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.670
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.410
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.650
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-54.660
Rat (Acute)
3.170
Rat (Chronic Oral)
1.850
Fathead Minnow
5.070
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
466.900
Hydration Free Energy
-3.570
Log(D) at pH=7.4
3.290
Log(P)
3.13
Log S
-5.15
Log(Vapor Pressure)
-8.8
Melting Point
230.52
pKa Acid
8.0
pKa Basic
2.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9501
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9501
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8894
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8894
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8772
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8772
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8150
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8150
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8016
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8016
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7976
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7976
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7930
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7930
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7756
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7756
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7712
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7712
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7601
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7601
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7588
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7588
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7441
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7441
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7439
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7439
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7438
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7438
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7335
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7335
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7290
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7290
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7236
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7236
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7204
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7204
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7170
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7170
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7149
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7149
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7143
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7143
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7110
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7110
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7045
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7045
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7021
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7021
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7009
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7009

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