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Dulcisflavan

Family: Plantae - Cistaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Isoflavanol

Canonical Smiles	O[C@@H]1Cc2c(O[C@@H]1c1ccc(c(c1)O)O)c(O)c(c(c2O)O)O
InChI	InChI=1S/C15H14O8/c16-7-2-1-5(3-8(7)17)14-9(18)4-6-10(19)11(20)12(21)13(22)15(6)23-14/h1-3,9,14,16-22H,4H2/t9-,14-/m1/s1
InChIKey	PONGJRZSHJPTOF-YMTOWFKASA-N
Formula	C₁₅H₁₄O₈
HBA	8
HBD	7
MW	322.27
Rotatable Bonds	1
TPSA	150.84
LogP	0.96
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.2
Exact Mass	322.07
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Helianthemum getulum	Cistaceae	Plantae	2020754

Showing of synonyms

Terfassi S, Dauvergne X, et al. (2022). First report on phytochemical investigation, antioxidant and antidiabetic activities of Helianthemum getulum. Natural product research, 2022, 36(11), 2806-2813. [View] [PubMed]

Pubchem: 11500740

Cas: 869669-61-4

Zinc: ZINC000015271337

Nmrshiftdb2: 60025319

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 322.27 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 322.27 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 322.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.92
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.71
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.61
Plasma Protein Binding: 88.5
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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 14.1
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.24
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.02
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.09
Micronucleos: Toxic
NR-AhR: Safe
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: 1.9
Rat (Acute): 2.31
Rat (Chronic Oral): 4.0
Fathead Minnow: 3.58
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 527.74
Hydration Free Energy: -10.95
Log(D) at pH=7.4: -0.12
Log(P): 0.38
Log S: -2.22
Log(Vapor Pressure): -9.63
Melting Point: 223.03
pKa Acid: 4.55
pKa Basic: 8.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9544
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9012
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8755
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8749
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8726
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.8652
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8650
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8645
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8567
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8544
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.8503
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.8499
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8498
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8482
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8444
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8370
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8350
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8312
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8306
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.8303
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	4	0.8283
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8276
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8266
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8246
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8225
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8210
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8193
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8192
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8186
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.8178
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8174
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8154
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8149
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8130
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8122
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	4	0.8099
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	4	0.8095
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8082
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8050
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	4	0.8033
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.8020
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7997
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.7990
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	4	0.7982
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7979
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7975
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.7974
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7945
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7941
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7935
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7926
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.7925
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	5	0.7890
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7886
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7885
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7869
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7850
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	5	0.7823
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7813
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7804
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7789
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7761
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7740
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	4	0.7739
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7708
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	6	0.7706
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7697
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7695
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7695
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7691
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7691
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7682
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	4	0.7662
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7657
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7646
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7633
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7625
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7614
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7598
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7593
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7593
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7575
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7574
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7573
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7572
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7566
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7563
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7557
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7555
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7553
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7515
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7505
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7482
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7481
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7471
Cytochrome P450 2C8	P10632	CP2C8_HUMAN	Homo sapiens	3	0.7466
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7452
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7440
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7418
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7414
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.7413
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7404
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7402
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7397
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7396
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7394
Ribosomal RNA small subunit methyltransferase E	Q5SKI6	Q5SKI6_THET8	Thermus thermophilus	4	0.7392
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7369
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	4	0.7367
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7357
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7344
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7341
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7321
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7318
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7309
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7307
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7300
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7294
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7291
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7289
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7282
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7281
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7266
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7264
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7256
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	4	0.7214
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7208
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7189
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7186
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7186
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7185
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7155
Purine nucleoside phosphorylase	P9WP00	PUNA_MYCTO	Mycobacterium tuberculosis	4	0.7153
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7148
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7148
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7148
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7126
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7117
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7111
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	5	0.7094
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7090
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7079
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7078
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7077
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7071
Leucine--tRNA ligase	P07813	SYL_ECOLI	Escherichia coli	3	0.7065
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7064
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7055
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7048
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7047
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7044
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7041
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7040
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	5	0.7034
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7034
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7009
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7005

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