ANPDB

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Neochamaejasmin B

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

Canonical Smiles	Oc1ccc(cc1)[C@@H]1Oc2cc(O)cc(c2C(=O)[C@H]1[C@H]1[C@H](Oc2c(C1=O)c(O)cc(c2)O)c1ccc(cc1)O)O
InChI	InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26-,29-,30+/m1/s1
InChIKey	RNQBLQALVMHBKH-JQYHKRKISA-N
Formula	C₃₀H₂₂O₁₀
HBA	10
HBD	6
MW	542.5
Rotatable Bonds	3
TPSA	173.98
LogP	4.49
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	542.12
Number of Lipinski Rule Violations	2

#	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]

Pubchem: 21636084

Cas: 90411-12-4

Zinc: ZINC000146803900

Nmrshiftdb2: 70059310

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 542.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 542.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.12
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.990
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.210
Plasma Protein Binding: 91.65
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: Inhibitor
CYP 2C9 Substrate: 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: 10.260
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.130
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.960
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.780
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: Toxic
T. Pyriformis: -5349.600
Rat (Acute): 2.240
Rat (Chronic Oral): 3.710
Fathead Minnow: 18.960
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: 553.210
Hydration Free Energy: -3.040
Log(D) at pH=7.4: 3.450
Log(P): 4.47
Log S: -6.33
Log(Vapor Pressure): -8.99
Melting Point: 339.79
pKa Acid: 9.79
pKa Basic: 5.69

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.9163
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8964
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8781
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8716
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8584
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8178
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8165
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7928
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7872
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7862
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.7852
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7837
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7823
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7799
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7786
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7781
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7658
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7649
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7647
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7623
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7503
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7488
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	5	0.7483
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7432
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7403
Glycerol kinase	P0A6F3	GLPK_ECOLI	Escherichia coli	4	0.7304
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7268
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7259
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7257
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	4	0.7211
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7204
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7203
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7202
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	4	0.7180
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7170
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7167
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7149
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7096
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	4	0.7091
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7054
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7036

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