[(3alpha,3'alpha,4beta,4'beta)-3,3']-dimethoxy-cis-[4,4'-bis(3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran)]-5,5',10,10'-tetraone - Compound Card

[(3alpha,3'alpha,4beta,4'beta)-3,3']-dimethoxy-cis-[4,4'-bis(3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran)]-5,5',10,10'-tetraone

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[(3alpha,3'alpha,4beta,4'beta)-3,3']-dimethoxy-cis-[4,4'-bis(3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran)]-5,5',10,10'-tetraone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles CO[C@H]1OCC2=C([C@@H]1[C@@H]1[C@@H](OC)OCC3=C1C(=O)c1c(C3=O)cccc1)C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C28H22O8/c1-33-27-21(19-17(11-35-27)23(29)13-7-3-5-9-15(13)25(19)31)22-20-18(12-36-28(22)34-2)24(30)14-8-4-6-10-16(14)26(20)32/h3-10,21-22,27-28H,11-12H2,1-2H3/t21-,22-,27+,28+/m1/s1
InChIKey KHPVSHARXQUBMH-BIQRORRISA-N
Formula C28H22O8
HBA 8
HBD 0
MW 486.48
Rotatable Bonds 3
TPSA 105.2
LogP 2.98
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 486.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas longiflora Rubiaceae Plantae 387060

Showing of synonyms

  • El-Hady S, Bukuru J, et al. (2002). New pyranonaphthoquinone and pyranonaphthohydroquinone from the roots of Pentas longiflora. Journal of Natural Products,2002,65(9),1377-1379. [View] [PubMed]
Pubchem: 10983749
Nmrshiftdb2: 70041906

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)C3=C(C2=O)C(COC3)C(COC4)C(C5=O)=C4C(=O)c(c56)cccc6

Level: 1

Mol. Weight: 486.48 g/mol

Structure

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

Level: 0

Mol. Weight: 486.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.600
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
81.33
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
10.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.360
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.530
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.710
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
Safe
T. Pyriformis
-1270.700
Rat (Acute)
3.700
Rat (Chronic Oral)
2.880
Fathead Minnow
9.480
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
544.430
Hydration Free Energy
-2.820
Log(D) at pH=7.4
2.340
Log(P)
3.71
Log S
-5.11
Log(Vapor Pressure)
-8.38
Melting Point
289.75
pKa Acid
4.12
pKa Basic
-0.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.9188
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.9188
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.9065
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.9065
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8472
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8472
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8445
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8445
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8191
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8191
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7627
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7627
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7623
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7623
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7611
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7611
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7608
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7608
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7585
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7585
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7569
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7569
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7513
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7513
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7485
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7485
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7396
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7396
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7280
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7280
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7190
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7190
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7181
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7181
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7129
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7129
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7116
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7116
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7072
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7072
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7045
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7045

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