NPASS Compound

Natural Product: NPC308771

Natural Product ID	NPC308771
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SSYRKFOBOISIEN-INIZCTEOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 48 51 0 0 0 0 0 0 0 0999 V2000 -0.9826 -2.1657 1.7746 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6329 -1.6361 0.4780 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4248 -2.2986 -0.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8847 -2.0853 -0.2321 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1484 -0.6418 -0.1968 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4169 -0.1766 -0.4725 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6978 1.1936 -0.4461 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6875 2.0760 -0.1400 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4312 1.5920 0.1315 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1441 0.2297 0.1071 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7418 -0.2002 0.4177 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1272 0.3915 -0.6740 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5400 0.1099 -0.5160 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1042 -1.0096 -1.0706 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4758 -1.2771 -0.9135 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2420 -0.3958 -0.1935 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6904 0.7308 0.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3383 0.9661 0.1962 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5051 1.5893 1.0858 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9122 2.7444 1.6556 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5851 -0.6379 -0.0275 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1524 -1.7952 -0.6045 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2137 3.3502 -0.1797 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6038 3.2786 -0.2746 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8404 1.9513 -0.6711 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1272 -2.1344 2.4685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8021 -1.5874 2.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3176 -3.2014 1.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1997 -3.3844 -0.4663 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2212 -1.8816 -1.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1950 -2.5306 0.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5038 -2.6017 -1.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2245 -0.8541 -0.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6429 2.2934 0.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4779 0.2080 1.4014 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0768 1.4959 -0.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2888 0.0450 -1.6580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5453 -1.7356 -1.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8945 -2.1622 -1.3584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9516 1.8717 0.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4705 3.3977 0.9025 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0659 2.3905 2.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6174 3.2786 2.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9142 -1.7505 -1.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5943 -2.6666 -0.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2436 -1.8548 -0.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0182 3.9723 -1.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0236 3.5087 0.7381 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 16 21 1 0 21 22 1 0 8 23 1 0 23 24 1 0 24 25 1 0 11 2 1 0 18 13 1 0 10 5 1 0 25 7 1 0 1 26 1 0 1 27 1 0 1 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 6 33 1 0 9 34 1 0 11 35 1 1 12 36 1 0 12 37 1 0 14 38 1 0 15 39 1 0 18 40 1 0 20 41 1 0 20 42 1 0 20 43 1 0 22 44 1 0 22 45 1 0 22 46 1 0 24 47 1 0 24 48 1 0 M END

Standard InCHIKey	SSYRKFOBOISIEN-INIZCTEOSA-N
Standard InCHI	InChI=1S/C20H23NO4/c1-21-7-6-14-10-19-20(25-12-24-19)11-15(14)16(21)8-13-4-5-17(22-2)18(9-13)23-3/h4-5,9-11,16H,6-8,12H2,1-3H3/t16-/m0/s1
SMILES	CN1CCc2cc3c(cc2[C@@H]1Cc1ccc(c(c1)OC)OC)OCO3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	341.16	Volume:	350.589 ? Van der Waals volume.
Dense:	0.973	LogP:	2.654 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.658 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.629 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	40.16 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.854	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.744	Fsp³:	0.4
MCE-18:	69.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.264	Fluc inhibitor:	0.311 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.344 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.315 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.004	Promiscuous compounds:	0.577

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.701	MDCK Permeability:	-4.675
Pgp-inhibitor:	0.928	Pgp-substrate:	0.06
PAMPA:	0.013 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.25	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.574

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992	MRP1:	0.937
Plasma Protein Binding (PPB):	66.403%	Volume Distribution (VD):	0.274
Fu:	32.188% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.886
OATP1B3 inhibitor:	0.771	BCRP inhibitor:	0.158
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	0.163
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.169 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

7.481

Half-life (T1/2):

2.345

ADMET: Toxicity

hERG Blockers:	0.505	hERG Blockers (10um):	0.574
Human Hepatotoxicity (H-HT):	0.76	Drug-induced Liver Injury (DILI):	0.339
AMES Toxicity:	0.671	Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.823	Skin Sensitization:	0.488
Carcinogencity:	0.751	Eye Corrosion:	0.005
Eye Irritation:	0.641	Respiratory Toxicity:	0.553
Drug-induced Neurotoxicity:	0.884	Ototoxicity:	0.595
Hematotoxicity:	0.287	Drug-induced Nephrotoxicity:	0.361
Genotoxicity:	0.644	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.076	Hek293 Cytotoxicity:	0.467
BCF:	1.854 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.956 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.009 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.845 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	twig	n.a.	PMID[16204994]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	leaves	Lai-I, Pingtung County, Taiwan	2005-May	PMID[20704331]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39064968]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15911	Streptomyces graminofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13040	Veretillum cynomorium	Species	Veretillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6615	Aplidium solidum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7036	Davidsonia pruriens	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13631	Microglossa pyrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12296	Sphaerechinus granularis	Species	Toxopneustidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14086	Parthenium confertum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3521	Geranium collinum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14366	Youngia japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14485	Eriocephalus kingesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7878	Lysastrosoma anthosticta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6615	Aplidium solidum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14086	Parthenium confertum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8632	Aralia hispida	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2770	Pyropolyporus fomentarius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12064	Lychnophora pinaster	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14485	Eriocephalus kingesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1202	Psathyrotes ramosissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11607	Marrubium parviflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1946	Veronica stricta	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13755	Gonotheca helianthoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20068	Fusarium striatum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13241	Coprosma foetidissima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3521	Geranium collinum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14223	Harpullia cupanioides	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13040	Veretillum cynomorium	Species	Veretillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26228	Phymatopteris hastata	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10936	Andira retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14996	Lobelia syphilitica	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6241	Girgensohnia oppositiflora	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14344	Trifolium diffusum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13631	Microglossa pyrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2075	Zanthoxylum ocumarense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5040	Polygonatum polyanthemum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12818	Lespedeza maximowiczi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7036	Davidsonia pruriens	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14885	Lilium rubrum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7878	Lysastrosoma anthosticta	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15098	Cyttaria johowii	Species	Cyttariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16090	Panicum crus-galli	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16174	Scleropyrum wallichianum	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12296	Sphaerechinus granularis	Species	Toxopneustidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15911	Streptomyces graminofaciens	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14639	Balanophora polyandra	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14366	Youngia japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13929	Hypocrella bambusae	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11833	Dyssodia anthemidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6229	Chenopodiastrum murale	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC308771 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	31968
0.1-0.2	15868
0.2-0.3	1555
0.3-0.4	250
0.4-0.5	149
0.5-0.6	48
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC213206
0.875	High Similarity	NPC188163
0.875	High Similarity	NPC328750
0.7451	Intermediate Similarity	NPC314682
0.7069	Intermediate Similarity	NPC27887
0.678	Remote Similarity	NPC247639
0.678	Remote Similarity	NPC475959
0.678	Remote Similarity	NPC25084
0.6552	Remote Similarity	NPC135538
0.6552	Remote Similarity	NPC24233
0.6316	Remote Similarity	NPC185838
0.6143	Remote Similarity	NPC73492
0.6143	Remote Similarity	NPC299990
0.6034	Remote Similarity	NPC474915
0.6	Remote Similarity	NPC317272
0.6	Remote Similarity	NPC268503
0.6	Remote Similarity	NPC226708
0.5735	Remote Similarity	NPC256012
0.5735	Remote Similarity	NPC610965
0.5714	Remote Similarity	NPC216459
0.5714	Remote Similarity	NPC41178
0.5714	Remote Similarity	NPC138487
0.5714	Remote Similarity	NPC603603
0.5625	Remote Similarity	NPC326205
0.5571	Remote Similarity	NPC276890
0.5429	Remote Similarity	NPC76682
0.5429	Remote Similarity	NPC10908
0.5429	Remote Similarity	NPC63646
0.5429	Remote Similarity	NPC317145
0.5429	Remote Similarity	NPC198498
0.5429	Remote Similarity	NPC115284
0.5417	Remote Similarity	NPC240841
0.5333	Remote Similarity	NPC475393
0.5323	Remote Similarity	NPC147390
0.5323	Remote Similarity	NPC428
0.5316	Remote Similarity	NPC24260
0.5312	Remote Similarity	NPC31311
0.5312	Remote Similarity	NPC234392
0.5303	Remote Similarity	NPC247389
0.5294	Remote Similarity	NPC14622
0.5294	Remote Similarity	NPC70290
0.5294	Remote Similarity	NPC215098
0.5294	Remote Similarity	NPC124302
0.5294	Remote Similarity	NPC73020
0.5217	Remote Similarity	NPC46744
0.5205	Remote Similarity	NPC12424
0.5205	Remote Similarity	NPC129518
0.5205	Remote Similarity	NPC251580
0.5147	Remote Similarity	NPC276944
0.5147	Remote Similarity	NPC238530
0.5143	Remote Similarity	NPC481430
0.5135	Remote Similarity	NPC603853
0.5094	Remote Similarity	NPC233029
0.5094	Remote Similarity	NPC210148
0.5072	Remote Similarity	NPC481429
0.5072	Remote Similarity	NPC481428
0.5072	Remote Similarity	NPC481449
0.5068	Remote Similarity	NPC227060
0.5067	Remote Similarity	NPC290582
0.5067	Remote Similarity	NPC217748
0.5067	Remote Similarity	NPC182052
0.5067	Remote Similarity	NPC271013
0.5067	Remote Similarity	NPC42663
0.5067	Remote Similarity	NPC15414
0.5067	Remote Similarity	NPC480587

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC308771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4549
0.1-0.2	4338
0.2-0.3	222
0.3-0.4	31
0.4-0.5	5
0.5-0.6	4
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD4664	Clinical (unspecified phase)
0.5429	Remote Similarity	NPD8099	Discontinued
0.5294	Remote Similarity	NPD4420	Pre-clinical
0.5135	Remote Similarity	NPD8156	Discontinued
0.5067	Remote Similarity	NPD8095	Phase 1

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data