(10R)-3',4'-dihydro-1,4,8,3',8',9'-hexahydroxy-3,3'-dimethyl-[10,7'-bianthracene]-9,1'(10H,2'H)-dione - Compound Card

(10R)-3',4'-dihydro-1,4,8,3',8',9'-hexahydroxy-3,3'-dimethyl-[10,7'-bianthracene]-9,1'(10H,2'H)-dione

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(10R)-3',4'-dihydro-1,4,8,3',8',9'-hexahydroxy-3,3'-dimethyl-[10,7'-bianthracene]-9,1'(10H,2'H)-dione

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Dimeric Anthracene Derivative
Canonical Smiles O=C1CC(C)(O)Cc2c1cc1c(c2)ccc(c1O)[C@H]1c2cccc(c2C(=O)c2c1c(O)c(C)cc2O)O
InChI InChI=1S/C30H24O7/c1-13-8-21(32)25-26(27(13)34)23(16-4-3-5-20(31)24(16)29(25)36)17-7-6-14-9-15-11-30(2,37)12-22(33)18(15)10-19(14)28(17)35/h3-10,23,31-32,34-35,37H,11-12H2,1-2H3/t23-,30?/m1/s1
InChIKey YZKIFCYWZMVWKM-ZCQJSQKNSA-N
Formula C30H24O7
HBA 7
HBD 5
MW 496.52
Rotatable Bonds 1
TPSA 135.29
LogP 4.58
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 496.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine abyssinica Asphodelaceae Plantae 2511937

Showing of synonyms

  • Wanjohi JM, Yenesew A, et al. (2005). Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica. Tetrahedron,2005,61(10),2667-2674. [View] [PubMed]
Pubchem: 102208950

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(c(c23)cccc3)c(cc4)cc(c5)c4cc(c56)CCCC6=O

Level: 1

Mol. Weight: 496.52 g/mol

Structure

SMILES: O=C1CCCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 496.52 g/mol

Structure

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 496.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
91.94
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.07
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.86
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.42
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
Toxic
T. Pyriformis
-1019.02
Rat (Acute)
2.59
Rat (Chronic Oral)
3.52
Fathead Minnow
7.58
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
577.88
Hydration Free Energy
-3.2
Log(D) at pH=7.4
3.45
Log(P)
4.47
Log S
-5.09
Log(Vapor Pressure)
-10.57
Melting Point
290.89
pKa Acid
6.63
pKa Basic
6.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8031
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8031
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7919
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7919
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7589
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7589
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7580
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7580
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7442
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7442
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7394
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7394
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7292
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7292
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7246
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7246
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7226
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7226
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7194
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7194
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7134
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7134
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7096
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7096
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7092
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7092
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7056
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7056

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