Dorsmanin I - Compound Card

Dorsmanin I

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Dorsmanin I

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles CC(=CCc1c2O[C@@H](CC(=O)c2c(c2c1OC(C)(C)C=C2)O)c1ccc(c(c1)O)O)C
InChI InChI=1S/C25H26O6/c1-13(2)5-7-16-23-15(9-10-25(3,4)31-23)22(29)21-19(28)12-20(30-24(16)21)14-6-8-17(26)18(27)11-14/h5-6,8-11,20,26-27,29H,7,12H2,1-4H3/t20-/m0/s1
InChIKey MUADCOGGQPLCBH-FQEVSTJZSA-N
Formula C25H26O6
HBA 6
HBD 3
MW 422.48
Rotatable Bonds 3
TPSA 96.22
LogP 5.2
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 422.17
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pseudarthria hookeri Leguminosae/Fabaceae Plantae 992776
2 Dorstenia mannii Moraceae Plantae 194258
3 Dorstenia mannii Moraceae Plantae 194258

Showing of synonyms

  • Tchamgoue J, Hafizur R, et al. (2016). Flavonoids and other constituents with insulin secretion activity from Pseudarthria hookeri. Phytochemistry Letters, 2016, 17, 181-186. [View]
  • Ngadjui BT, Kouam SF, et al. (2000). Prenylated flavonoids from the aerial parts of Dorstenia mannii.. Phytochemistry,2000, 55(8), 915-919. [View] [PubMed]
  • Ngadjui BT, Kouam SF, et al. (2000). Prenylated flavonoids from the aerial parts of Dorstenia mannii.. Phytochemistry,2000, 55(8), 915-919. [View] [PubMed]
Pubchem: 637828
Nmrshiftdb2: 70009539

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)OC(CC3=O)c4ccccc4

Level: 1

Mol. Weight: 422.48 g/mol

Structure

SMILES: O=C1CCOc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 422.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 422.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
81.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.39
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.56
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.18
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
-32.39
Rat (Acute)
2.45
Rat (Chronic Oral)
2.44
Fathead Minnow
4.99
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
506.04
Hydration Free Energy
-4.97
Log(D) at pH=7.4
3.69
Log(P)
5.45
Log S
-5.79
Log(Vapor Pressure)
-9.89
Melting Point
203.89
pKa Acid
7.55
pKa Basic
5.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9307
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9152
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.9105
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9015
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8944
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8844
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8825
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8650
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8625
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8616
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8499
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8446
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8424
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8415
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8358
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8303
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8054
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7966
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7889
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7879
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7875
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7792
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7728
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7692
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7667
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7628
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7613
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7612
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7600
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7583
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7581
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7565
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7557
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7515
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7501
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7498
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7497
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7493
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7486
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7478
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7467
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7458
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7435
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7434
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7411
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7401
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7373
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7371
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7369
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7342
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7337
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7335
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7315
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7313
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7303
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7301
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7300
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7275
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7261
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7253
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7242
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7240
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7235
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7201
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7196
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7162
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7148
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7144
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7139
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7101
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7093
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7084
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7075
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7070
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7069
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7066
Kinesin heavy chain Q41460 Q41460_SOLTU Solanum tuberosum 3 0.7066
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7045
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7039
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7036
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7015
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7007

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