NPASS Compound

Natural Product: NPC78222

Natural Product ID	NPC78222
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(6As)-2,9,10-Trimethoxy-6-Methyl-5,6,6A,7-Tetrahydro-4H-Dibenzo[De,G]Quinoline-1-Ol
IUPAC Name	(6aS)-2,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1-ol
Synonyms	(+)-Thaliporphine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1397308
PubChem CID	6992288
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

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 49 52 0 0 0 0 0 0 0 0999 V2000 -3.3630 -1.8817 -1.3882 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7770 -0.6311 -0.9566 N 0 0 0 0 0 4 0 0 0 0 0 0 -3.8135 0.2831 -0.6175 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5997 1.0526 0.6718 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1789 1.4481 0.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 2.6913 0.9918 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3690 3.0028 1.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5725 2.0131 0.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1485 0.7532 0.4109 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1064 -0.3227 0.0946 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4465 -0.0346 0.0871 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3324 -1.0764 -0.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8392 -2.3249 -0.5212 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4891 -2.5831 -0.5048 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6010 -1.5565 -0.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8251 -1.9134 -0.1923 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7874 -0.8499 0.0883 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2273 0.4675 0.4049 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7114 -3.3834 -0.8445 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1800 -4.6470 -1.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7064 -0.8829 -0.2677 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1960 0.4050 0.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8797 2.3799 0.7396 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0652 4.3081 1.3158 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9115 5.2920 1.6051 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8754 -2.2118 -2.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2095 -2.6580 -0.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4446 -1.7514 -1.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2532 -0.2347 -1.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7793 -0.2698 -0.5662 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9512 1.0324 -1.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2719 1.9571 0.5931 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8907 0.4249 1.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4247 3.4612 1.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9283 0.8832 0.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1241 -3.5848 -0.7390 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -2.7276 0.5967 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0733 -2.4374 -1.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4109 -1.1343 0.9902 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9663 -5.3990 -1.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5940 -4.9903 -0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4809 -4.5962 -1.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2858 0.4922 -0.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7027 1.1377 -0.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9297 0.6386 1.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2492 3.2313 1.1152 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4439 5.5583 0.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6091 4.9601 2.4137 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4269 6.2092 1.9987 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 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 13 19 1 0 19 20 1 0 12 21 1 0 21 22 1 0 8 23 1 0 7 24 1 0 24 25 1 0 17 2 1 0 18 5 2 0 18 9 1 0 15 10 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 0 3 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 6 34 1 0 11 35 1 0 14 36 1 0 16 37 1 0 16 38 1 0 17 39 1 1 20 40 1 0 20 41 1 0 20 42 1 0 22 43 1 0 22 44 1 0 22 45 1 0 23 46 1 0 25 47 1 0 25 48 1 0 25 49 1 0 M CHG 1 2 1 M END

Standard InCHIKey	SAERKXUSZPTMCQ-AWEZNQCLSA-N
Standard InCHI	InChI=1S/C20H23NO4/c1-21-6-5-11-8-17(25-4)20(22)19-13-10-16(24-3)15(23-2)9-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/p+1/t14-/m0/s1
SMILES	C[NH+]1CCc2cc(c(c3-c4cc(c(cc4C[C@H]1c23)OC)OC)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	341.16	Volume:	350.589 ? Van der Waals volume.
Dense:	0.973	LogP:	1.942 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.226 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.791 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	20.0
TPSA:	51.16 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.929	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.986	Fsp³:	0.4
MCE-18:	75.571 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.415	Fluc inhibitor:	0.039 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.57 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.279 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.004	Promiscuous compounds:	0.868

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.006	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.099	Pgp-substrate:	0.525
PAMPA:	0.008 ? 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):	0.208
20% Bioavailability (F20%):	0.754	30% Bioavailability (F30%):	0.73
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151	MRP1:	0.939
Plasma Protein Binding (PPB):	71.619%	Volume Distribution (VD):	0.051
Fu:	30.2% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.975
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.828
BSEP inhibitor:	0.745

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.889	CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.419
CYP2B6-substrate:	0.972	CYP2C8-inhibitor:	0.106
HLM stability:	0.253 ? 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):

6.334

Half-life (T1/2):

3.052

ADMET: Toxicity

hERG Blockers:	0.383	hERG Blockers (10um):	0.68
Human Hepatotoxicity (H-HT):	0.546	Drug-induced Liver Injury (DILI):	0.055
AMES Toxicity:	0.597	Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.92	Skin Sensitization:	0.609
Carcinogencity:	0.699	Eye Corrosion:	0.001
Eye Irritation:	0.134	Respiratory Toxicity:	0.957
Drug-induced Neurotoxicity:	0.84	Ototoxicity:	0.376
Hematotoxicity:	0.161	Drug-induced Nephrotoxicity:	0.296
Genotoxicity:	0.816	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.309	Hek293 Cytotoxicity:	0.359
BCF:	1.518 ? 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:	4.03 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.221 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.604 ? 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
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088436]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19445517]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO27020	Thalictrum alpinum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25629555]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO1320	Thalictrum ichangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28026	Grifola frondosa	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1114	Cetraria australiensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8077	Artocarpus incisa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10295	Amanita pantherina	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO595	Tephrosia falciformis	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO435	Bohadschia marmorata	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28026	Grifola frondosa	Species	Schizophyllaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1320	Thalictrum ichangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27020	Thalictrum alpinum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2654	Beaumontia grandiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27020	Thalictrum alpinum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8077	Artocarpus incisa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1320	Thalictrum ichangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2654	Beaumontia grandiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10295	Amanita pantherina	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25039	Pseudognaphalium viscosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO620	Streptococcus pyogenes	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28026	Grifola frondosa	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO435	Bohadschia marmorata	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1114	Cetraria australiensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10518	Chrysanthemum myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO595	Tephrosia falciformis	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2654	Beaumontia grandiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1320	Thalictrum ichangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27020	Thalictrum alpinum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8077	Artocarpus incisa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	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

Activity Type	# Activity
Potency	30
Activity	12

Activity Type	# Activity
Individual protein	25
Tissue	3
Protein-protein interaction	2
Others	3
Non-molecular	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT1226	Individual protein	Caspase-7	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT151	Individual protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT277	Individual protein	Caspase-1	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT55	Individual protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT501	Individual protein	Alpha-galactosidase A	Homo sapiens	Potency	=	56234.1	nM	PubChem BioAssay data set
NPT58	Individual protein	Bloom syndrome protein	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT48	Individual protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	34435.5	nM	PubChem BioAssay data set
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT46	Individual protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	5011.9	nM	PubChem BioAssay data set
NPT46	Individual protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	44668.4	nM	PubChem BioAssay data set
NPT583	Individual protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	8912.5	nM	PubChem BioAssay data set
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	5011.9	nM	PubChem BioAssay data set
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PubChem BioAssay data set
NPT583	Individual protein	Inositol monophosphatase 1	Rattus norvegicus	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT53	Individual protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	50118.7	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	163.0	%	PMID[23305495]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	154.0	%	PMID[23305495]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	125.0	%	PMID[23305495]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	243.0	%	PMID[23305495]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	180.0	%	PMID[23305495]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	110.0	%	PMID[23305495]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	140.0	%	PMID[23305495]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	104.0	%	PMID[23305495]
NPT2606	Tissue	Heart	Rattus norvegicus	Activity	=	82.0	%	PMID[23305495]
NPT2606	Tissue	Heart	Rattus norvegicus	Activity	=	86.0	%	PMID[23305495]
NPT2606	Tissue	Heart	Rattus norvegicus	Activity	=	92.0	%	PMID[23305495]
NPT2	Others	Unspecified	n.a.	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	14125.4	nM	PubChem BioAssay data set

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 NPC78222 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	31145
0.1-0.2	17299
0.2-0.3	1371
0.3-0.4	34
0.4-0.5	3
0.5-0.6	5
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7119	Intermediate Similarity	NPC166014
0.5625	Remote Similarity	NPC302527
0.5484	Remote Similarity	NPC196447
0.5484	Remote Similarity	NPC306843
0.5231	Remote Similarity	NPC210918
0.5072	Remote Similarity	NPC149090

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC78222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6293
0.1-0.2	2820
0.2-0.3	37
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

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