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Chlorophyll a

Family: Rubiaceae
Kingdom: Plantae
Class: Chlorin
- Subclass: Porphyrin Derivative

Canonical Smiles	CCC1=C(C2=NC1=CC3=C(C4=C([N-]3)C(=C5[C@H]([C@@H](C(=N5)C=C6C(=C(C(=C2)[N-]6)C=C)C)C)CCC(=O)OC/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C4=O)C(=O)OC)C)C.[Mg+2]
InChI	InChI=1S/C55H73N4O5.Mg/c1-13-39-35(8)42-28-44-37(10)41(24-25-48(60)64-27-26-34(7)23-17-22-33(6)21-16-20-32(5)19-15-18-31(3)4)52(58-44)50-51(55(62)63-12)54(61)49-38(11)45(59-53(49)50)30-47-40(14-2)36(9)43(57-47)29-46(39)56-42;/h13,26,28-33,37,41,51H,1,14-25,27H2,2-12H3,(H-,56,57,58,59,61);/q-1;+2/p-1/b34-26+;/t32-,33-,37+,41+,51-;/m1./s1
InChIKey	ATNHDLDRLWWWCB-AENOIHSZSA-M
Formula	C₅₅H₇₂MgN₄O₅
HBA	7
HBD	0
MW	893.51
Rotatable Bonds	20
TPSA	123.65
LogP	12.84
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	65
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	892.54
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Coffea canephora	Rubiaceae	Plantae	49390

Showing of synonyms

Mewaba S, Happi E, et al. (2022). Antibacterial compounds of the cultivated Robusta coffee: Coffea canephora Pierre ex A. Froehner. Scientific African, 2022, 16, e01274. [View]

Pubchem: 12085802

Cas: 479-61-8

Gnps: CCMSLIB00000211464

Chebi: 18230

Comptox: DTXSID90889346

Drugbank: DB02133

Pdb Ligand: CLA

CPRiL: 407539

SMILES: O=C1Cc(c2c13)c4nc(CC4)cc5ccc([n-]5)cc6ccc(n6)cc([n-]2)c3

Level: 0

Mol. Weight: 350.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.74
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 1797.38
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 235581.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.83
Plasma Protein Binding: 90.24
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: 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: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 6.62
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -5480.51
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.96
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.44
Micronucleos: Toxic
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: -427572679.78
Rat (Acute): 2.64
Rat (Chronic Oral): 3.39
Fathead Minnow: 539728.63
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 48084634.99
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 0.5
Log(P): 14.79
Log S: -6.23
Log(Vapor Pressure): -1583376.15
Melting Point: 141.85
pKa Acid: -11460.17
pKa Basic: -59.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.9776
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9525
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.9475
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.9265
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.9083
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8962
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8848
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8778
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8637
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8492
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.8474
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8394
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8378
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8229
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8223
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8143
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.8138
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8063
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8033
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.8015
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.8002
Nuclear receptor coactivator 2	Q15596	NCOA2_HUMAN	Homo sapiens	3	0.7986
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7976
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7975
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7959
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7945
Retinoic acid receptor RXR	Q8T5C6	RXR_BIOGL	Biomphalaria glabrata	3	0.7928
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7927
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	3	0.7883
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7863
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7861
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7835
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7834
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7817
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7815
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7815
Bacteriorhodopsin	P02945	BACR_HALSA	Halobacterium salinarum	3	0.7789
Cartilage oligomeric matrix protein	P35444	COMP_RAT	Rattus norvegicus	3	0.7788
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7755
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7742
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7729
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7721
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7718
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	3	0.7715
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7697
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7693
Retinol-binding protein 4	P02753	RET4_HUMAN	Homo sapiens	3	0.7672
Putative cytochrome P450 120	Q59990	CP120_SYNY3	Synechocystis sp	3	0.7643
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7637
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7634
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7630
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7616
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7610
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7604
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7584
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7581
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7571
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7568
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7553
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7549
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7544
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7533
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.7521
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7517
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7508
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	2	0.7498
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7496
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7495
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7491
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7488
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7482
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.7442
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7423
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7416
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7416
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7414
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7409
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	2	0.7405
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7389
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7385
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7379
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7367
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7358
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7357
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7343
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7331
Oxysterols receptor LXR-beta	P55055	NR1H2_HUMAN	Homo sapiens	3	0.7323
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7323
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7318
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7317
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7297
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7275
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7234
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7224
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7219
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7218
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7211
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7207
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7202
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7191
Retinoic acid receptor beta	P10826	RARB_HUMAN	Homo sapiens	3	0.7179
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7178
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7169
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7113
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7112
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	2	0.7071
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7062
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7055
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	3	0.7050
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7041
Japanin	M1MR49	M1MR49_RHIAP	Rhipicephalus appendiculatus	3	0.7032
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7025
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	3	0.7023
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7022
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7015

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