NPASS Compound

Natural Product: NPC140925

Natural Product ID	NPC140925
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FTODBIPDTXRIGS-CYBMUJFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	12310452
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-O-methylated flavonoids

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 36 38 0 0 0 0 0 0 0 0999 V2000 4.9487 -0.4685 -1.9114 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8889 0.0858 -0.6164 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6893 0.2529 0.0373 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5257 -0.1285 -0.5853 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2955 0.0300 0.0552 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2702 0.5735 1.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4295 0.9666 1.9686 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6474 0.7936 1.2973 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7756 1.1935 1.9707 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0134 -0.3681 -0.5796 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4213 -1.7228 -0.1291 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8230 -1.8106 0.2865 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2596 -2.9036 0.6978 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7468 -0.6822 0.2467 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0867 -0.8490 0.5420 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9070 0.2638 0.4849 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4273 1.5077 0.1474 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0890 1.6313 -0.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2330 0.5406 -0.0934 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9053 0.6511 -0.3752 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3073 2.5945 0.1071 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5646 -2.0961 0.8797 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9690 -0.2866 -2.3162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8259 -1.5882 -1.8879 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1790 -0.0788 -2.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4755 -0.5610 -1.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3023 0.6912 1.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3478 1.3829 2.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4914 1.7924 1.5855 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2090 -0.4275 -1.6810 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2281 -2.0759 0.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2681 -2.5008 -0.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9608 0.1761 0.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6938 2.6000 -0.4062 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9708 3.5411 0.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8479 -2.7205 0.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 17 21 1 0 15 22 1 0 8 3 1 0 20 10 1 0 19 14 1 0 1 23 1 0 1 24 1 0 1 25 1 0 4 26 1 0 6 27 1 0 7 28 1 0 9 29 1 0 10 30 1 6 11 31 1 0 11 32 1 0 16 33 1 0 18 34 1 0 21 35 1 0 22 36 1 0 M END

Standard InCHIKey	FTODBIPDTXRIGS-CYBMUJFWSA-N
Standard InCHI	InChI=1S/C16H14O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-6,13,17-19H,7H2,1H3/t13-/m1/s1
SMILES	COc1cc(ccc1O)[C@H]1CC(=O)c2c(cc(cc2O1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	302.08	Volume:	293.909 ? Van der Waals volume.
Dense:	1.028	LogP:	2.412 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.543 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.19 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	18.0
TPSA:	96.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.789	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.89	Fsp³:	0.188
MCE-18:	57.789 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.531	Fluc inhibitor:	0.711 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.275 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.321 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.355	Promiscuous compounds:	0.085

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.096	MDCK Permeability:	-4.811
Pgp-inhibitor:	0.99	Pgp-substrate:	0.051
PAMPA:	0.103 ? 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):	0.01
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.921
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.86
Plasma Protein Binding (PPB):	96.563%	Volume Distribution (VD):	-0.15
Fu:	3.366% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	1.0
BSEP inhibitor:	0.951

ADMET: Metabolism

CYP1A2-inhibitor:	0.997	CYP1A2-substrate:	0.425
CYP2C19-inhibitor:	0.322	CYP2C19-substrate:	0.968
CYP2C9-inhibitor:	0.964	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.402	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.022	CYP3A4-substrate:	0.963
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.981 ? 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):

6.686

Half-life (T1/2):

1.501

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.494
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.393
AMES Toxicity:	0.771	Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.708	Skin Sensitization:	0.702
Carcinogencity:	0.691	Eye Corrosion:	0.04
Eye Irritation:	0.994	Respiratory Toxicity:	0.596
Drug-induced Neurotoxicity:	0.398	Ototoxicity:	0.253
Hematotoxicity:	0.142	Drug-induced Nephrotoxicity:	0.357
Genotoxicity:	0.954	RPMI-8226 Immunitoxicity:	0.145
A549 Cytotoxicity:	0.511	Hek293 Cytotoxicity:	0.738
BCF:	1.068 ? 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:	3.504 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.571 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.796 ? 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
NPO138	Daphniphyllum paxianum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17887722]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[21911291]
NPO1346	Nerine bowdenii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22312717]
NPO11877	Penicillium herquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26848504]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28802670]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31675225]
NPO1831	Pseudodistoma arborescens	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8450325]
NPO11877	Penicillium herquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8609085]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14686	Justicia adhatoda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25542	Streptomyces pactum	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6622	Artemisia klotzchiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8127	Veronica arvensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9252	Adina sessilifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11657	Angelica lucida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1697	Bitis gabonica	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11934	Castanea vesca	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13472	Cotula cinerea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO138	Daphniphyllum paxianum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21255	Hymenoxys insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3995	Limonium sinense	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11823	Marine actinobacterium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1831	Pseudodistoma arborescens	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6845	Mimusops caffra	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5735	Solidago serotina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1346	Nerine bowdenii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11877	Penicillium herquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14564	Oophaga pumilio	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8127	Veronica arvensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6622	Artemisia klotzchiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8127	Veronica arvensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14686	Justicia adhatoda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14686	Justicia adhatoda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9252	Adina sessilifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11877	Penicillium herquei	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8127	Veronica arvensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5735	Solidago serotina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10149	Lespedeza bicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14564	Oophaga pumilio	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4848	Chrysopa septempunctata	Species	Chrysopidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6845	Mimusops caffra	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11823	Marine actinobacterium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21255	Hymenoxys insignis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11657	Angelica lucida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3995	Limonium sinense	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9153	Sorbaria sorbifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2002	Drupa concatenata	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO138	Daphniphyllum paxianum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25542	Streptomyces pactum	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4969	Sesbania bispinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6622	Artemisia klotzchiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1831	Pseudodistoma arborescens	Species	Pseudodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1697	Bitis gabonica	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1346	Nerine bowdenii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11934	Castanea vesca	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13472	Cotula cinerea	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

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 NPC140925 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	25450
0.1-0.2	19054
0.2-0.3	4012
0.3-0.4	1023
0.4-0.5	212
0.5-0.6	67
0.6-0.7	19
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236637
0.7451	Intermediate Similarity	NPC32441
0.7451	Intermediate Similarity	NPC79943
0.7407	Intermediate Similarity	NPC302950
0.7368	Intermediate Similarity	NPC477841
0.7273	Intermediate Similarity	NPC474836
0.717	Intermediate Similarity	NPC274784
0.717	Intermediate Similarity	NPC338131
0.717	Intermediate Similarity	NPC20709
0.7037	Intermediate Similarity	NPC321011
0.7037	Intermediate Similarity	NPC294852
0.7037	Intermediate Similarity	NPC188679
0.7015	Intermediate Similarity	NPC602605
0.6812	Remote Similarity	NPC158188
0.6792	Remote Similarity	NPC243083
0.6792	Remote Similarity	NPC13768
0.6792	Remote Similarity	NPC287246
0.6727	Remote Similarity	NPC486095
0.6604	Remote Similarity	NPC182421
0.6481	Remote Similarity	NPC295261
0.6481	Remote Similarity	NPC296490
0.6452	Remote Similarity	NPC108456
0.6441	Remote Similarity	NPC326037
0.6441	Remote Similarity	NPC13858
0.6406	Remote Similarity	NPC35038
0.6316	Remote Similarity	NPC599987
0.625	Remote Similarity	NPC200761
0.625	Remote Similarity	NPC107586
0.6182	Remote Similarity	NPC12296
0.6129	Remote Similarity	NPC109223
0.6129	Remote Similarity	NPC10937
0.6104	Remote Similarity	NPC476365
0.5965	Remote Similarity	NPC329203
0.5965	Remote Similarity	NPC222342
0.5873	Remote Similarity	NPC17170
0.5873	Remote Similarity	NPC477840
0.5862	Remote Similarity	NPC606248
0.5735	Remote Similarity	NPC473272
0.5694	Remote Similarity	NPC195796
0.5672	Remote Similarity	NPC473990
0.5672	Remote Similarity	NPC611447
0.5645	Remote Similarity	NPC258630
0.5616	Remote Similarity	NPC27337
0.5616	Remote Similarity	NPC479054
0.5616	Remote Similarity	NPC472598
0.5616	Remote Similarity	NPC236934
0.5522	Remote Similarity	NPC312973
0.55	Remote Similarity	NPC18727
0.55	Remote Similarity	NPC310135
0.5493	Remote Similarity	NPC475784
0.5467	Remote Similarity	NPC474055
0.5455	Remote Similarity	NPC174953
0.5441	Remote Similarity	NPC69531
0.5441	Remote Similarity	NPC88964
0.5439	Remote Similarity	NPC225153
0.5439	Remote Similarity	NPC479876
0.5424	Remote Similarity	NPC73028
0.5424	Remote Similarity	NPC324386
0.5395	Remote Similarity	NPC472634
0.5373	Remote Similarity	NPC134783
0.5362	Remote Similarity	NPC118256
0.5345	Remote Similarity	NPC6407
0.5345	Remote Similarity	NPC545184
0.5342	Remote Similarity	NPC36916
0.5342	Remote Similarity	NPC36
0.5342	Remote Similarity	NPC7154
0.5342	Remote Similarity	NPC125039
0.5342	Remote Similarity	NPC7688
0.5333	Remote Similarity	NPC469764
0.5323	Remote Similarity	NPC16435
0.5303	Remote Similarity	NPC106976
0.5294	Remote Similarity	NPC475790
0.5278	Remote Similarity	NPC227579
0.5278	Remote Similarity	NPC214166
0.5278	Remote Similarity	NPC606364
0.527	Remote Similarity	NPC138688
0.527	Remote Similarity	NPC72787
0.527	Remote Similarity	NPC217795
0.527	Remote Similarity	NPC58223
0.5256	Remote Similarity	NPC472635
0.5254	Remote Similarity	NPC150648
0.5167	Remote Similarity	NPC99597
0.5167	Remote Similarity	NPC300668
0.5167	Remote Similarity	NPC255106
0.5167	Remote Similarity	NPC235165
0.5139	Remote Similarity	NPC224851
0.5139	Remote Similarity	NPC474038
0.5139	Remote Similarity	NPC26195
0.5088	Remote Similarity	NPC329225
0.5088	Remote Similarity	NPC147686
0.5085	Remote Similarity	NPC201227
0.5085	Remote Similarity	NPC258474
0.5085	Remote Similarity	NPC603284
0.5082	Remote Similarity	NPC210084
0.5082	Remote Similarity	NPC475267
0.5079	Remote Similarity	NPC52530
0.5075	Remote Similarity	NPC134171
0.5072	Remote Similarity	NPC470890
0.5067	Remote Similarity	NPC488550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC140925 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4553
0.1-0.2	4468
0.2-0.3	109
0.3-0.4	12
0.4-0.5	1
0.5-0.6	4
0.6-0.7	1
0.7-0.8	2
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
0.7451	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1934	Phase 0
0.6792	Remote Similarity	NPD1550	Phase 2
0.5342	Remote Similarity	NPD6166	Phase 2
0.5342	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5342	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5088	Remote Similarity	NPD1549	Phase 2

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