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Sargassaceae meroditerpenoid 3

Family: Chromista - Sargassaceae-Fucaceae
Kingdom: Chromista
Class: Terpenoid
- Subclass: Meroditerpenoid

Canonical Smiles	COc1cc(C)c2c(c1)C=C[C@@](O2)(C)CC1=C(CC(O)(C)C)C(=O)[C@@]2([C@](C1)(C)CCC2)C
InChI	InChI=1S/C28H38O4/c1-18-13-21(31-7)14-19-9-12-27(5,32-23(18)19)16-20-15-26(4)10-8-11-28(26,6)24(29)22(20)17-25(2,3)30/h9,12-14,30H,8,10-11,15-17H2,1-7H3/t26-,27+,28-/m1/s1
InChIKey	RHDGWMARJHUFRF-OZNIXHKMSA-N
Formula	C₂₈H₃₈O₄
HBA	4
HBD	1
MW	438.61
Rotatable Bonds	5
TPSA	55.76
LogP	6.18
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.61
Exact Mass	438.28
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cystoseira baccata	Sargassaceae-Fucaceae	Chromista	2823494

Showing of synonyms

Mokrini R, Mesaoud MB, et al. (2008). Meroditerpenoids and derivatives from the brown alga Cystoseira baccata and their antifouling properties. Journal of Natural Products,2008,71(11),1806-1181. [View] [PubMed]

Pubchem: 25156145

Zinc: ZINC000045285067

Nmrshiftdb2: 60043622

Chembl: CHEMBL572862

No compound-protein relationship available.

SMILES: C1CCC(C12)CC(=CC2=O)CC(C=C3)Oc(c34)cccc4

Level: 1

Mol. Weight: 438.61 g/mol

SMILES: C1CCC(C12)CC=CC2=O

Level: 0

Mol. Weight: 438.61 g/mol

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 438.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.92
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.510
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.06

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.450
Plasma Protein Binding: 99.81
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.220
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.310
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.260
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.470
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: -48.760
Rat (Acute): 2.900
Rat (Chronic Oral): 2.040
Fathead Minnow: 4.590
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: 464.200
Hydration Free Energy: -3.510
Log(D) at pH=7.4: 4.720
Log(P): 6.27
Log S: -5.55
Log(Vapor Pressure): -7.5
Melting Point: 161.51
pKa Acid: 10.12
pKa Basic: 5.96

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8940
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8940
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8914
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8914
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8839
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8839
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8543
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8543
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8305
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8305
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.8290
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.8290
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.8213
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.8213
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.8047
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.8047
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7985
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7985
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7944
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7944
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7865
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7865
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7797
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7797
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7779
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7779
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7761
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7761
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7761
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7761
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7668
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7668
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7633
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7633
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7619
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7619
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7615
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7615
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7599
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7599
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7498
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7498
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7476
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7476
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7403
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7403
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7402
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7402
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7324
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7324
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7288
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7288
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7287
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7287
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7287
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7287
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7283
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7283
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7267
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7267
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7254
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7254
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7196
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7196
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7183
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7183
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7182
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7182
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	4	0.7181
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	4	0.7181
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7172
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7172
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7153
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7153
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.7149
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7149
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.7149
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7149
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7080
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7080
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7061
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7061
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	3	0.7059
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	3	0.7059
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7030
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7030
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7025
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7025
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7018
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7018

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