NPASS Compound

Natural Product: NPC149602

Natural Product ID	NPC149602
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XQZVZULJKVALRI-LBPRGKRZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3337756
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000004] Organosulfur compounds [CHEMONTID:0000491] Sulfoxides

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 27 26 0 0 0 0 0 0 0 0999 V2000 2.3852 1.5674 0.4854 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2408 0.0240 0.4852 S 0 0 0 0 0 4 0 0 0 0 0 0 4.6851 0.2284 0.0687 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4733 -1.3065 -0.3767 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1288 -1.7329 0.1059 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0761 -0.6556 0.0527 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2659 -1.1935 0.5362 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3208 -0.1461 0.5041 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5260 0.3733 -0.8967 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5760 1.3885 -0.8915 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2825 2.5463 -0.4841 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2386 4.1056 -0.1219 S 0 0 0 0 0 0 0 0 0 0 0 0 1.6890 1.6913 -0.3682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1409 2.3911 0.3480 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8545 1.8189 1.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4425 -1.1595 -1.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1568 -2.2076 -0.2659 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1632 -2.1786 1.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7178 -2.5729 -0.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0415 -0.2294 -0.9454 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3172 0.1671 0.7829 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 -1.5872 1.5611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5347 -2.0515 -0.1300 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9661 0.7324 1.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3021 -0.4895 0.8717 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7882 -0.4049 -1.6225 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5871 0.8814 -1.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 2 3 2 0 2 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 1 0 10 11 2 0 11 12 2 0 1 13 1 0 1 14 1 0 1 15 1 0 4 16 1 0 4 17 1 0 5 18 1 0 5 19 1 0 6 20 1 0 6 21 1 0 7 22 1 0 7 23 1 0 8 24 1 0 8 25 1 0 9 26 1 0 9 27 1 0 M END

Standard InCHIKey	XQZVZULJKVALRI-LBPRGKRZSA-N
Standard InCHI	InChI=1S/C8H15NOS2/c1-12(10)7-5-3-2-4-6-9-8-11/h2-7H2,1H3/t12-/m0/s1
SMILES	C[S@](=O)CCCCCCN=C=S

Calculated Properties

Physi-Chem Properties

Molecular Weight:	205.06	Volume:	198.456 ? Van der Waals volume.
Dense:	1.033	LogP:	0.908 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.958 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.325 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	2.0
TPSA:	35.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.276	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.463	Fsp³:	0.875
MCE-18:	1.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.02	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.884	Promiscuous compounds:	0.446

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.871	MDCK Permeability:	-4.693
Pgp-inhibitor:	0.262	Pgp-substrate:	0.017
PAMPA:	0.184 ? 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):	0.001
20% Bioavailability (F20%):	0.035	30% Bioavailability (F30%):	0.007
50% Bioavailability (F50%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096	MRP1:	0.356
Plasma Protein Binding (PPB):	49.769%	Volume Distribution (VD):	0.122
Fu:	53.71% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.001	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.027	CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.953	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.562	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.039	CYP2D6-substrate:	0.992
CYP3A4-inhibitor:	0.914	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.893	CYP2C8-inhibitor:	0.987
HLM stability:	0.001 ? 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):

9.023

Half-life (T1/2):

1.264

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.033
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.0	Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	1.0	Eye Corrosion:	1.0
Eye Irritation:	1.0	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.002
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.002
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.097
BCF:	1.75 ? 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:	4.866 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.839 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.49 ? 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
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50097a033]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12802735]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18384095]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014168]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[22779710]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22779710]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540838]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295708]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25102361]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25306330]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31625742]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35986990]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36770740]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985747]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37087263]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37924762]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38306771]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38474614]
NPO15118	Paederia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21557	Woodsia manchuriensis	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28646	Streptomyces argenteolus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28422	Sabia japonica	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28195	Phlogacanthus tubiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20714	Lobophytum schoedei	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27905	Eritrichium sericeum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28070	Chrysosplenium americanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23326	Bohadschia vitiensis	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27829	Aplophyllum pedicellatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28263	Anemone tomentosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28556	Streptomyces pentaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15118	Paederia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO16314	Clematis terniflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15118	Paederia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17111	Myriactis humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27829	Aplophyllum pedicellatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21557	Woodsia manchuriensis	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20714	Lobophytum schoedei	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23326	Bohadschia vitiensis	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28422	Sabia japonica	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28646	Streptomyces argenteolus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28195	Phlogacanthus tubiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28141	Colpomenia sinuosa	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13645	Armoracia rusticana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28070	Chrysosplenium americanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27905	Eritrichium sericeum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28556	Streptomyces pentaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19765	Melampyrum nemorosum	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28263	Anemone tomentosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16314	Clematis terniflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11079	Centaurea regia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13725	Kallstroemia pubescens	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15118	Paederia chinensis	Species	Rubiaceae	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
GI	2
IC50	2

Activity Type	# Activity
Cell line	4

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
NPT171	Cell line	MRC5	Homo sapiens	GI	=	20.0	%	PMID[25299679]
NPT81	Cell line	A549	Homo sapiens	GI	=	50.0	%	PMID[25299679]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	17580.0	nM	PMID[25299679]
NPT81	Cell line	A549	Homo sapiens	IC50	=	7540.0	nM	PMID[25299679]

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 NPC149602 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	38330
0.1-0.2	11144
0.2-0.3	329
0.3-0.4	31
0.4-0.5	13
0.5-0.6	4
0.6-0.7	2
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC140734
0.8333	Intermediate Similarity	NPC292366
0.8333	Intermediate Similarity	NPC105023
0.68	Remote Similarity	NPC602302
0.64	Remote Similarity	NPC600275
0.5862	Remote Similarity	NPC235767
0.5714	Remote Similarity	NPC180872
0.56	Remote Similarity	NPC245814
0.5517	Remote Similarity	NPC266113

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC149602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7229
0.1-0.2	1873
0.2-0.3	48
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