Herbarin - Compound Card

Herbarin

Select a section from the left sidebar

Herbarin

Structure
Zoomed Structure
  • Family: Fungi - Chaetosphaeriales
  • Kingdom: Fungi
  • Class: Xanthone
Canonical Smiles COc1cc(OC)c2c(c1)C(=O)C1=C(C2=O)COC(C1)(C)O
InChI InChI=1S/C16H16O6/c1-16(19)6-10-11(7-22-16)15(18)13-9(14(10)17)4-8(20-2)5-12(13)21-3/h4-5,19H,6-7H2,1-3H3
InChIKey MQWLANHTCHDMAR-UHFFFAOYSA-N
Formula C16H16O6
HBA 6
HBD 1
MW 304.3
Rotatable Bonds 2
TPSA 82.06
LogP 1.51
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 304.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chaetosphaeronema sp. Chaetosphaeriales Fungi 1755421

Showing of synonyms

  • Osman M, El-Beih A, et al. (2018). Production of herbarin and dehydroherbarin by endophytic Chaetosphaeronema sp. (KY321184) isolated from Nepeta septemcrenata and evaluation of their bioactivities. South African Journal of Botany, 2018, 117, 174-183. [View]
Pubchem: 3084629
Nmrshiftdb2: 80001846

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)C3=C(C2=O)CCOC3

Level: 0

Mol. Weight: 304.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.53
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.710
Plasma Protein Binding
25.03
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.690
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.100
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.410
Micronucleos
Toxic
NR-AhR
Toxic
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
3.340
Rat (Acute)
2.600
Rat (Chronic Oral)
2.560
Fathead Minnow
4.260
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
394.900
Hydration Free Energy
-9.090
Log(D) at pH=7.4
1.410
Log(P)
1.54
Log S
-3.24
Log(Vapor Pressure)
-6.0
Melting Point
182.23
pKa Acid
5.57
pKa Basic
3.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9560
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8678
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8544
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8465
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8297
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7960
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7940
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7852
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7776
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7652
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7574
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7561
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7468
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7329
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7290
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7217
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7217
GMP synthase [glutamine-hydrolyzing] Q8IJR9 Q8IJR9_PLAF7 Plasmodium falciparum 4 0.7203
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7198
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7182
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7144
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7139
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7127
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7114
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7082
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7077
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7036
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7027
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7001

Download SDF