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Prinoidin

Family: Plantae - Rhamnaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone

Canonical Smiles	CC(=O)O[C@H]1[C@H](Oc2cc(O)c3c(c2)Cc2c(C3=O)c(O)cc(c2)C)O[C@H]([C@@H]([C@H]1OC(=O)C)O)C
InChI	InChI=1S/C25H26O10/c1-10-5-14-7-15-8-16(9-18(29)20(15)22(31)19(14)17(28)6-10)35-25-24(34-13(4)27)23(33-12(3)26)21(30)11(2)32-25/h5-6,8-9,11,21,23-25,28-30H,7H2,1-4H3/t11-,21-,23+,24+,25-/m0/s1
InChIKey	DARHCWIFQPMQTB-NRVKTMTASA-N
Formula	C₂₅H₂₆O₁₀
HBA	10
HBD	3
MW	486.47
Rotatable Bonds	4
TPSA	148.82
LogP	1.89
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	486.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhamnus prinoides	Rhamnaceae	Plantae	280022
2	Rhamnus prinoides	Rhamnaceae	Plantae	280022
3	Rhamnus prinoides	Rhamnaceae	Plantae	280022

Showing of synonyms

Abegaz BM, Dagne E. (1988). Anthracene derivatives of Rhamnus prinoides. Bulletin of the Chemical Society of Ethiopia,1988,2(1),15-20. [View] [PubMed]
Abegaz BM, Peter MG. (1995). Emodin and emodinanthrone rhamnoside acetates from fruits of Rhamnus prinoides. Phytochemistry,1995,39(6),1411-1414. [View] [PubMed]
Abegaz BM, Kebede T. (1995). Geshoidin: A bitter principle of Rhamnus prinoides and other constituents of the leaves. Bulletin of the Chemical Society of Ethiopia,1995,9(2),107-114. [View] [PubMed]

Pubchem: 25107461

Cas: 118985-30-1

Zinc: ZINC000040876894

Nmrshiftdb2: 60076415

Chembl: CHEMBL465506

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1Cc(c23)cc(cc3)OC4CCCCO4

Level: 1

Mol. Weight: 486.47 g/mol

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

Level: 0

Mol. Weight: 486.47 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 486.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.67
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.87
Plasma Protein Binding: 80.32
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.92
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.84
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.26
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -209.45
Rat (Acute): 2.73
Rat (Chronic Oral): 2.78
Fathead Minnow: 4.47
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 500.44
Hydration Free Energy: -3.02
Log(D) at pH=7.4: 2.35
Log(P): 3.81
Log S: -4.02
Log(Vapor Pressure): -10.26
Melting Point: 202.21
pKa Acid: 7.17
pKa Basic: 2.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.9120
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.9120
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8988
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8988
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8958
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8958
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.8873
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.8873
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8846
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8846
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8834
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8834
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8764
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8764
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8724
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8724
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8599
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8599
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8494
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8494
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8407
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8407
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8399
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8399
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8391
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8391
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.8202
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.8202
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8201
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8201
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8148
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8148
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	4	0.8108
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	4	0.8108
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8040
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8040
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7995
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7995
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7898
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7898
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7820
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7820
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7810
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7810
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7804
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7804
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7750
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7750
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7734
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7734
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7730
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7730
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7684
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7684
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7669
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7669
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7658
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7658
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7631
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7631
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7614
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7614
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7609
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7609
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7599
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7599
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7572
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7572
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7564
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7564
Enoyl-acyl carrier reductase	Q6UCJ9	Q6UCJ9_TOXGO	Toxoplasma gondii	4	0.7519
Enoyl-acyl carrier reductase	Q6UCJ9	Q6UCJ9_TOXGO	Toxoplasma gondii	4	0.7519
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7481
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7481
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7445
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7445
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7433
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7433
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7421
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7421
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7419
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7419
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7403
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7403
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7387
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7387
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7381
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7381
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7360
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7360
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7357
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7357
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7339
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7339
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7324
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7324
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7308
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7308
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7297
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7297
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7240
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7240
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7216
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7216
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7208
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7208
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7188
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7188
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7168
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7168
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7164
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7164
Thymidine phosphorylase	P07650	TYPH_ECOLI	Escherichia coli	4	0.7148
Thymidine phosphorylase	P07650	TYPH_ECOLI	Escherichia coli	4	0.7148
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7142
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7142
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2	Q9R1E6	ENPP2_MOUSE	Mus musculus	4	0.7135
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2	Q9R1E6	ENPP2_MOUSE	Mus musculus	4	0.7135
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.7112
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.7112
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7109
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7109
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7058
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7058
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7044
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7044
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7044
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7044
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7028
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7028

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