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Grandiflorenic acid

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Diterpene

Canonical Smiles	C=C1CC23CC1CC=C3[C@]1([C@H](CC2)[C@@](C)(CCC1)C(=O)O)C
InChI	InChI=1S/C20H28O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h6,14-15H,1,4-5,7-12H2,2-3H3,(H,21,22)/t14?,15-,18+,19+,20?/m0/s1
InChIKey	RJIPNPHMQGDUBW-MZWQVCBVSA-N
Formula	C₂₀H₂₈O₂
HBA	1
HBD	1
MW	300.44
Rotatable Bonds	1
TPSA	37.3
LogP	4.96
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.75
Exact Mass	300.21
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Aspilia mossambicensis	Asteraceae	Plantae	1932724

Showing of synonyms

Page JE, Balza F, et al. (1992). Biologically active diterpenes from Aspilia mossambicensis, a chimpanzee medicinal plant.. Phytochemistry,1992,31(10),3437-3439. [View] [PubMed]

Pubchem: 161387

Cas: 22338-67-6

CPRiL: 436355

SMILES: C=C(C1)C(C2)CC=C(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 300.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.52
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.5
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.42

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.26
Plasma Protein Binding: 73.05
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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 1.56
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.24
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.02
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.25
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 0.25
Rat (Acute): 2.44
Rat (Chronic Oral): 2.14
Fathead Minnow: 3.93
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 361.9
Hydration Free Energy: -3.02
Log(D) at pH=7.4: 2.31
Log(P): 5.69
Log S: -5.31
Log(Vapor Pressure): -6.48
Melting Point: 166.5
pKa Acid: 5.8
pKa Basic: 7.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8952
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8952
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8786
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8786
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8022
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8022
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8014
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8014
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7712
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7712
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7623
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7623
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7595
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7595
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7527
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7527
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7481
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7481
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7450
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7450
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7450
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7450
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7412
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7412
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7399
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7399
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7357
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7357
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7330
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7330
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7305
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7305
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7294
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7294
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7249
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7249
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7196
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7196
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7179
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7179
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7167
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7167
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7090
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7090
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7075
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7075
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7070
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7070
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7057
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7057
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7010
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7010

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