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3'-epi-dihydrodaphnodorin B

Family: Plantae - Thymelaeaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavan

Canonical Smiles	Oc1ccc(cc1)[C@H]1Oc2c(C[C@@H]1O)c(O)cc1c2[C@H](C(=O)c2ccc(cc2)O)[C@H](O1)c1ccc(cc1)O
InChI	InChI=1S/C30H24O8/c31-18-7-1-15(2-8-18)27(36)26-25-24(37-29(26)17-5-11-20(33)12-6-17)14-22(34)21-13-23(35)28(38-30(21)25)16-3-9-19(32)10-4-16/h1-12,14,23,26,28-29,31-35H,13H2/t23-,26+,28+,29+/m0/s1
InChIKey	HCCPKLWFVUKUEZ-GQQJEHHBSA-N
Formula	C₃₀H₂₄O₈
HBA	8
HBD	5
MW	512.51
Rotatable Bonds	4
TPSA	136.68
LogP	4.65
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.17
Exact Mass	512.15
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Thymelaea hirsuta	Thymelaeaceae	Plantae	69845

Showing of synonyms

Badawy A, Hassanean H, et al. (2011). Isolates From Thymelaea Hirsuta Inhibit Progression Of Hepatocellular Carcinoma In Vitro And In Vivo. Natural Product Research, 2011,35(11),1799–1798. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)C2C(c3ccccc3)Oc(c24)ccc5c4OC(CC5)c6ccccc6

Level: 3

Mol. Weight: 512.51 g/mol

SMILES: c1ccccc1C(=O)C2COc(c23)ccc4c3OC(CC4)c5ccccc5

Level: 2

Mol. Weight: 512.51 g/mol

SMILES: c1ccccc1C(=O)C2C(c3ccccc3)Oc(c24)ccc5c4OCCC5

Level: 2

Mol. Weight: 512.51 g/mol

SMILES: c1ccccc1C(C2)Oc(c23)ccc4c3OC(CC4)c5ccccc5

Level: 2

Mol. Weight: 512.51 g/mol

SMILES: c1ccccc1C(=O)C2COc(c23)ccc4c3OCCC4

Level: 1

Mol. Weight: 512.51 g/mol

SMILES: C1COc(c12)ccc3c2OC(CC3)c4ccccc4

Level: 1

Mol. Weight: 512.51 g/mol

SMILES: C1CCOc2c1ccc(c23)OC(C3)c4ccccc4

Level: 1

Mol. Weight: 512.51 g/mol

SMILES: C1COc(c12)ccc3c2OCCC3

Level: 0

Mol. Weight: 512.51 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 512.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.97
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.920
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.78

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.300
Plasma Protein Binding: 94.92
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: 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: 9.110
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.400
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.040
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.760
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -3218.360
Rat (Acute): 2.310
Rat (Chronic Oral): 2.800
Fathead Minnow: 16.070
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 553.450
Hydration Free Energy: -3.080
Log(D) at pH=7.4: 3.760
Log(P): 3.53
Log S: -5.1
Log(Vapor Pressure): -10.08
Melting Point: 280.79
pKa Acid: 7.29
pKa Basic: 6.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.9457
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9343
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9341
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9249
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8774
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.8674
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8672
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	5	0.8653
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8608
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.8594
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.8541
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8241
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8177
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.8173
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8162
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	4	0.8041
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7902
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7899
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7885
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7857
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7848
Bromodomain-containing protein 9	Q9H8M2	BRD9_HUMAN	Homo sapiens	3	0.7833
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7816
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7737
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7730
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7719
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7704
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7679
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7664
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7601
Prostaglandin reductase 1	Q14914	PTGR1_HUMAN	Homo sapiens	4	0.7581
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7569
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.7567
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7552
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7543
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7529
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7489
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7486
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7443
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7426
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7402
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7371
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7369
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7349
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7324
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7302
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7290
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7287
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7286
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7259
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7239
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7239
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7234
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7218
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7212
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7202
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7198
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7187
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7171
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7164
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7142
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7132
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7129
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7102
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7100
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7097
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7094
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7093
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7090
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7086
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7084
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7064
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7058
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	3	0.7048
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7028
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7025
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7006

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