NPASS Compound

Natural Product: NPC520488

Natural Product ID	NPC520488
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	9-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-yl-non-8-en-1-one
IUPAC Name	9-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-yl-non-8-en-1-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 51 53 0 0 0 0 0 0 0 0999 V2000 -3.2613 -1.2821 -0.3915 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2066 -0.0278 -0.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8932 0.5211 0.1957 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8050 -0.5093 0.4270 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0829 -1.4178 1.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0717 -2.4331 1.8991 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3313 -3.4983 0.9870 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9843 -3.1570 -0.2903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2338 -2.3672 -0.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4488 -1.1769 -0.5845 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6696 -0.4280 -0.3542 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6971 -0.9055 0.4224 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8388 -0.1527 0.6103 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9724 1.0742 0.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0004 2.0150 0.0639 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6884 3.0684 -0.8268 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3444 2.8276 -1.2103 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9489 1.5717 -0.7520 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8179 0.8131 -0.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3974 0.6867 -0.2304 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5512 2.1008 0.0066 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4292 2.5056 -1.1711 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4681 1.3758 -1.1303 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7014 0.1872 -0.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5527 1.1596 -0.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9624 1.1889 1.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5708 -0.9489 -0.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1065 0.1026 0.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0414 -1.9857 1.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2090 -0.7753 2.4740 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4828 -2.9349 2.8542 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8264 -1.8681 2.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5764 -4.1760 0.8185 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0522 -4.1920 1.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4303 -4.1787 -0.6559 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3595 -2.8129 -1.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9635 -2.8596 0.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6803 -0.7471 -1.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6529 -1.8715 0.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6580 -0.5128 1.2186 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3603 3.0599 -1.7026 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7748 4.0501 -0.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0401 1.2527 -1.5603 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1708 2.2646 0.9316 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6099 2.6478 0.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8702 3.4841 -0.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8606 2.3971 -2.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8797 1.1681 -2.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2887 1.6729 -0.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6790 -0.6294 -1.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2583 -0.2053 0.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 2 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 19 11 1 0 24 20 1 0 18 14 1 0 3 25 1 0 3 26 1 0 4 27 1 0 4 28 1 0 5 29 1 0 5 30 1 0 6 31 1 0 6 32 1 0 7 33 1 0 7 34 1 0 8 35 1 0 8 36 1 0 9 37 1 0 10 38 1 0 12 39 1 0 13 40 1 0 16 41 1 0 16 42 1 0 19 43 1 0 21 44 1 0 21 45 1 0 22 46 1 0 22 47 1 0 23 48 1 0 23 49 1 0 24 50 1 0 24 51 1 0 M END

Standard InCHIKey	VBHDFZGBKBFFDM-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C20H27NO3/c22-20(21-13-7-8-14-21)10-6-4-2-1-3-5-9-17-11-12-18-19(15-17)24-16-23-18/h5,9,11-12,15H,1-4,6-8,10,13-14,16H2
SMILES	O=C(CCCCCCC=CC1=CC=C2OCOC2=C1)N1CCCC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	329.2	Volume:	352.992 ? Van der Waals volume.
Dense:	0.933	LogP:	4.258 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.249 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.622 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	17.0
TPSA:	38.77 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.664	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.206	Fsp³:	0.55
MCE-18:	32.516 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.062	Fluc inhibitor:	0.922 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.19 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.599 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.066

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776	MDCK Permeability:	-4.597
Pgp-inhibitor:	0.244	Pgp-substrate:	0.02
PAMPA:	0.104 ? 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%):	0.028	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.314

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888	MRP1:	0.368
Plasma Protein Binding (PPB):	86.894%	Volume Distribution (VD):	-0.149
Fu:	13.249% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.416
OATP1B3 inhibitor:	0.857	BCRP inhibitor:	0.012
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.596	CYP2C19-substrate:	0.467
CYP2C9-inhibitor:	0.419	CYP2C9-substrate:	0.453
CYP2D6-inhibitor:	0.996	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.068	CYP3A4-substrate:	0.993
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.526
HLM stability:	0.977 ? 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):

4.496

Half-life (T1/2):

0.32

ADMET: Toxicity

hERG Blockers:	0.514	hERG Blockers (10um):	0.61
Human Hepatotoxicity (H-HT):	0.561	Drug-induced Liver Injury (DILI):	0.056
AMES Toxicity:	0.464	Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.43	Skin Sensitization:	0.991
Carcinogencity:	0.374	Eye Corrosion:	0.149
Eye Irritation:	0.811	Respiratory Toxicity:	0.538
Drug-induced Neurotoxicity:	0.44	Ototoxicity:	0.239
Hematotoxicity:	0.109	Drug-induced Nephrotoxicity:	0.494
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.221	Hek293 Cytotoxicity:	0.48
BCF:	1.459 ? 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:	4.192 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.602 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.892 ? 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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26213786]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31096694]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31766491]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38067483]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38474459]
NPO17517	Artemisia arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38592817]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18069	Streptomyces coelicoflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17517	Artemisia arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16447	Potato virus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13999	Piper trichostachyon	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16048	Euphorbia serrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15734	Euchresta horsfeldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15893	Solandra guttata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21786	Culcitium serratifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2913	Tabebuia pentaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15369	Tabernaemontana rupicola	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17297	Caragana pygmaea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13999	Piper trichostachyon	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13999	Piper trichostachyon	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13999	Piper trichostachyon	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15369	Tabernaemontana rupicola	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17517	Artemisia arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15893	Solandra guttata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17297	Caragana pygmaea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15734	Euchresta horsfeldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21786	Culcitium serratifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16048	Euphorbia serrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18069	Streptomyces coelicoflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2913	Tabebuia pentaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16447	Potato virus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13999	Piper trichostachyon	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	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 NPC520488 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	20742
0.1-0.2	27448
0.2-0.3	1477
0.3-0.4	130
0.4-0.5	24
0.5-0.6	13
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC194359
1.0	High Similarity	NPC28641
1.0	High Similarity	NPC180647
1.0	High Similarity	NPC225745
0.8462	Intermediate Similarity	NPC318862
0.7455	Intermediate Similarity	NPC230698
0.7455	Intermediate Similarity	NPC99078
0.7455	Intermediate Similarity	NPC96406
0.7273	Intermediate Similarity	NPC193673
0.7069	Intermediate Similarity	NPC220923
0.7069	Intermediate Similarity	NPC196609
0.6897	Remote Similarity	NPC328419
0.6786	Remote Similarity	NPC159150
0.661	Remote Similarity	NPC73883
0.661	Remote Similarity	NPC251454
0.6604	Remote Similarity	NPC167096
0.6604	Remote Similarity	NPC605721
0.6441	Remote Similarity	NPC103947
0.6441	Remote Similarity	NPC45783
0.6415	Remote Similarity	NPC217574
0.614	Remote Similarity	NPC255817
0.614	Remote Similarity	NPC136330
0.5965	Remote Similarity	NPC94280
0.5932	Remote Similarity	NPC205178
0.5932	Remote Similarity	NPC227218
0.5789	Remote Similarity	NPC605639
0.5714	Remote Similarity	NPC191302
0.5625	Remote Similarity	NPC156944
0.5614	Remote Similarity	NPC608515
0.5469	Remote Similarity	NPC152186
0.5373	Remote Similarity	NPC41331
0.5373	Remote Similarity	NPC291449
0.5345	Remote Similarity	NPC470707
0.5224	Remote Similarity	NPC71105
0.52	Remote Similarity	NPC127326

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC520488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4282
0.1-0.2	4734
0.2-0.3	127
0.3-0.4	5
0.4-0.5	1
0.5-0.6	0
0.6-0.7	1
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
0.614	Remote Similarity	NPD2492	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