NPASS Compound

Natural Product: NPC120052

Natural Product ID	NPC120052
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JSRLRXYURNHHDK-LSDHHAIUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101630410
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

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 46 49 0 0 0 0 0 0 0 0999 V2000 -4.9751 2.4159 1.3179 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0706 1.0664 0.9100 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8737 0.3615 0.6806 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6479 0.9710 0.8494 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4810 0.2772 0.6237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4725 -1.0588 0.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1987 -1.7315 -0.0069 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3462 -1.6812 -1.3920 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6099 -0.3284 -1.9488 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0526 0.1067 -1.9185 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6464 0.1716 -0.5797 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3226 -0.8872 -0.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8734 -0.8043 1.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7459 0.3454 1.9772 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0746 1.4278 1.4440 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5394 1.3200 0.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1053 2.4449 2.3909 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2228 2.1632 3.2345 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1757 0.7303 3.2510 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2515 -0.5282 -3.4371 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7631 -1.5243 -3.4019 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5497 -2.3751 -2.3369 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0071 -3.5239 -2.1642 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7101 -1.6440 0.0572 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8829 -0.9536 0.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0889 -1.6386 0.0903 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6063 2.5225 2.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0145 2.8417 1.3128 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3290 3.0251 0.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6250 2.0134 1.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5181 0.7725 0.7690 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5807 -1.4255 0.7516 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3596 -2.8267 0.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3398 -2.2349 -1.4577 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0365 0.4723 -1.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1527 1.1134 -2.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6326 -0.5752 -2.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4699 -1.8289 -0.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4092 -1.6620 1.6924 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0166 2.1938 -0.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1663 2.5275 2.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0324 2.5902 4.2228 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1098 -0.8490 -4.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2131 0.3929 -3.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7666 -2.6950 -0.2573 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6863 -1.4914 -0.7086 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 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 9 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 6 24 1 0 24 25 2 0 25 26 1 0 25 3 1 0 22 8 1 0 16 11 1 0 19 14 1 0 1 27 1 0 1 28 1 0 1 29 1 0 4 30 1 0 5 31 1 0 7 32 1 0 7 33 1 0 8 34 1 1 9 35 1 1 10 36 1 0 10 37 1 0 12 38 1 0 13 39 1 0 16 40 1 0 18 41 1 0 18 42 1 0 20 43 1 0 20 44 1 0 24 45 1 0 26 46 1 0 M END

Standard InCHIKey	JSRLRXYURNHHDK-LSDHHAIUSA-N
Standard InCHI	InChI=1S/C20H20O6/c1-23-17-4-2-13(8-16(17)21)7-15-14(10-24-20(15)22)6-12-3-5-18-19(9-12)26-11-25-18/h2-5,8-9,14-15,21H,6-7,10-11H2,1H3/t14-,15+/m0/s1
SMILES	COc1ccc(C[C@@H]2[C@@H](Cc3ccc4c(c3)OCO4)COC2=O)cc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	356.13	Volume:	354.536 ? Van der Waals volume.
Dense:	1.004	LogP:	2.378 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.74 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	74.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.831	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.209	Fsp³:	0.35
MCE-18:	69.222 ? 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:	0.421	Fluc inhibitor:	0.58 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.021 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.179 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.252	Promiscuous compounds:	0.389

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.895	MDCK Permeability:	-4.693
Pgp-inhibitor:	0.525	Pgp-substrate:	0.028
PAMPA:	0.241 ? 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):	0.002
20% Bioavailability (F20%):	0.507	30% Bioavailability (F30%):	0.05
50% Bioavailability (F50%):	0.569

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042	MRP1:	0.514
Plasma Protein Binding (PPB):	98.158%	Volume Distribution (VD):	-0.401
Fu:	1.894% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.961
OATP1B3 inhibitor:	0.812	BCRP inhibitor:	0.012
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.993	CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.834 ? 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):

3.004

Half-life (T1/2):

1.765

ADMET: Toxicity

hERG Blockers:	0.192	hERG Blockers (10um):	0.598
Human Hepatotoxicity (H-HT):	0.958	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.625	Skin Sensitization:	0.889
Carcinogencity:	0.837	Eye Corrosion:	0.003
Eye Irritation:	0.94	Respiratory Toxicity:	0.249
Drug-induced Neurotoxicity:	0.791	Ototoxicity:	0.611
Hematotoxicity:	0.614	Drug-induced Nephrotoxicity:	0.892
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.238
A549 Cytotoxicity:	0.392	Hek293 Cytotoxicity:	0.6
BCF:	1.323 ? 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:	3.975 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.238 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.81 ? 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
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11376004]
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1367428]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[18314958]
NPO11237	Bupleurum salicifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24242108]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32100544]
NPO11237	Bupleurum salicifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964800]
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[Article]
NPO16792	Nocardia pseudobrasiliensis	Species	Nocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7327	Aeromonas hydrophila	Species	Aeromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8414	Crella incrustans	Species	Crellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11400	Aster ptarmicoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2582	Plagiomnium undulatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16343	Galium album	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7991	Lactarius vellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4033	Corydalis gigantea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7991	Lactarius vellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12874	Sedum cepaea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11400	Aster ptarmicoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6669	Dysosma delavayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4033	Corydalis gigantea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7991	Lactarius vellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4033	Corydalis gigantea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10719	Centrosema haitense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7653	Mosla japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9496	Gomphostemma crinitum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9018	Millettia rubiginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11400	Aster ptarmicoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11237	Bupleurum salicifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4970	Torricellia tiliifolia	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3017	Artemisia caucasica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7991	Lactarius vellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2291	Saussurea pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6669	Dysosma delavayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12176	Streptomyces olivaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16343	Galium album	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16792	Nocardia pseudobrasiliensis	Species	Nocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7327	Aeromonas hydrophila	Species	Aeromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10354	Urbanodendron verrucosum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1460	Rubus phoenicolasius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20210	Lophozia floerkei	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17456	Echinochloa esculenta	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4033	Corydalis gigantea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3614	Echinopepon bigelovii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12659	Hopea brevipetiolaris	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6235	Exobasidium vaccinii	Species	Exobasidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12874	Sedum cepaea	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2582	Plagiomnium undulatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9648	Maharanga bicolor	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10560	Adenia fruticosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1164	Osteospermum hyoseroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8414	Crella incrustans	Species	Crellidae	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 NPC120052 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	21449
0.1-0.2	24644
0.2-0.3	3260
0.3-0.4	345
0.4-0.5	103
0.5-0.6	25
0.6-0.7	22
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8136	Intermediate Similarity	NPC282291
0.8136	Intermediate Similarity	NPC166137
0.8103	Intermediate Similarity	NPC145569
0.7818	Intermediate Similarity	NPC205915
0.7736	Intermediate Similarity	NPC110958
0.7736	Intermediate Similarity	NPC19890
0.7544	Intermediate Similarity	NPC176586
0.7544	Intermediate Similarity	NPC210354
0.7414	Intermediate Similarity	NPC191158
0.7414	Intermediate Similarity	NPC177644
0.6875	Remote Similarity	NPC216223
0.6721	Remote Similarity	NPC5310
0.6721	Remote Similarity	NPC300776
0.6721	Remote Similarity	NPC176814
0.6721	Remote Similarity	NPC4982
0.6721	Remote Similarity	NPC606629
0.6613	Remote Similarity	NPC293757
0.6613	Remote Similarity	NPC668
0.6545	Remote Similarity	NPC223807
0.6379	Remote Similarity	NPC92693
0.6364	Remote Similarity	NPC174512
0.6308	Remote Similarity	NPC487679
0.6308	Remote Similarity	NPC487678
0.6271	Remote Similarity	NPC68779
0.6271	Remote Similarity	NPC108598
0.6271	Remote Similarity	NPC40237
0.619	Remote Similarity	NPC106920
0.619	Remote Similarity	NPC15811
0.6133	Remote Similarity	NPC245615
0.6102	Remote Similarity	NPC211386
0.6071	Remote Similarity	NPC476748
0.6	Remote Similarity	NPC143895
0.5873	Remote Similarity	NPC273657
0.5857	Remote Similarity	NPC478703
0.5857	Remote Similarity	NPC478704
0.5821	Remote Similarity	NPC56184
0.5714	Remote Similarity	NPC478705
0.5692	Remote Similarity	NPC3982
0.5614	Remote Similarity	NPC72796
0.5507	Remote Similarity	NPC169973
0.5439	Remote Similarity	NPC600801
0.541	Remote Similarity	NPC192255
0.541	Remote Similarity	NPC474288
0.5238	Remote Similarity	NPC158737
0.5238	Remote Similarity	NPC274356
0.5238	Remote Similarity	NPC101748
0.5167	Remote Similarity	NPC325295
0.5167	Remote Similarity	NPC76308
0.5143	Remote Similarity	NPC76687
0.5125	Remote Similarity	NPC299706
0.5125	Remote Similarity	NPC115466
0.5125	Remote Similarity	NPC61604
0.5082	Remote Similarity	NPC11453
0.5079	Remote Similarity	NPC171550
0.5079	Remote Similarity	NPC134764
0.5075	Remote Similarity	NPC185908
0.5075	Remote Similarity	NPC482891

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC120052 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4124
0.1-0.2	4834
0.2-0.3	174
0.3-0.4	17
0.4-0.5	1
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