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Nagilactone D

Family: Plantae - Podocarpaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Norditerpene Lactone

Canonical Smiles	CCc1oc(=O)cc2c1C[C@H]1OC(=O)[C@@]3([C@H]1[C@]2(C)[C@@H]1O[C@@H]1[C@@H]3O)C
InChI	InChI=1S/C18H20O6/c1-4-9-7-5-10-13-17(2,8(7)6-11(19)22-9)15-12(24-15)14(20)18(13,3)16(21)23-10/h6,10,12-15,20H,4-5H2,1-3H3/t10-,12-,13-,14+,15-,17-,18-/m1/s1
InChIKey	UEZYUDAMQBJVJP-CQVMLLNQSA-N
Formula	C₁₈H₂₀O₆
HBA	6
HBD	1
MW	332.35
Rotatable Bonds	1
TPSA	89.27
LogP	0.71
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	332.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Podocarpus gracilior	Podocarpaceae	Plantae	165205

Showing of synonyms

Faiella L, Temraz A, et al. (2012). Terpenoids from the leaves of Podocarpus gracilior. Phytochemistry Letters,2012,5(2),297-300. [View]

Pubchem: 3084330

Cas: 19891-53-3

Nmrshiftdb2: 60071035

Chembl: CHEMBL4217857

Comptox: DTXSID60173668

No compound-protein relationship available.

SMILES: C12C(O2)CC3C4C(OC3=O)Cc5c(C14)cc(=O)oc5

Level: 0

Mol. Weight: 332.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.29
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.62
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.35
Plasma Protein Binding: 38.89
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 16.4
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.1
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: 5.57
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: Toxic
T. Pyriformis: -1.4
Rat (Acute): 4.26
Rat (Chronic Oral): 1.86
Fathead Minnow: 3.96
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 412.45
Hydration Free Energy: -6.48
Log(D) at pH=7.4: 0.64
Log(P): 0.21
Log S: -2.42
Log(Vapor Pressure): -7.78
Melting Point: 190.63
pKa Acid: 5.58
pKa Basic: 4.38

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8907
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8907
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8581
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8581
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8538
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8538
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8147
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8147
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8132
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8132
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7770
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7770
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7711
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7711
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7710
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7710
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7617
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7617
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7563
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7563
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7541
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7541
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7470
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7470
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7443
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7443
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7410
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7410
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7306
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7306
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7252
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7252
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7222
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7222
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7207
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7207
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7135
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7135
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7057
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7057
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7039
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7039
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7027
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7027

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