NPASS Compound

Natural Product: NPC480086

Natural Product ID	NPC480086
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JLYYLRJNDUJLOW-RWFJALSOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15378750
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 61 64 0 0 0 0 0 0 0 0999 V2000 6.0467 2.5476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9320 1.5439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2439 0.0766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5054 2.0074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0275 2.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3199 3.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6255 2.2680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6387 0.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6519 -0.7318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9443 0.0296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2367 0.7910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2235 2.2909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 3.0294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8719 4.1870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9436 4.1700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2681 5.6345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4688 3.8965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3463 0.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1895 -1.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8192 -2.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 -1.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1614 3.5513 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0504 1.4328 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0430 3.6623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5228 0.0196 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9335 1.6567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0442 2.6480 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0309 1.6933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5021 3.6501 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4473 2.5185 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4373 4.5020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2139 4.0198 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4296 3.7552 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8479 -2.2190 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0569 -1.2572 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4309 -1.6032 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0503 -0.9837 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4686 -1.3930 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7116 1.0644 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7621 -0.6140 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8927 3.6334 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7029 2.0435 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8259 5.3445 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8393 5.2750 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1371 3.3811 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6408 5.1473 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1644 -0.9169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5524 -2.9405 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5598 -2.0954 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1247 -3.2609 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6580 -3.3388 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0283 -2.5730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 -2.0982 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4811 -1.1383 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8631 -0.7175 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 8 7 1 6 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 2 0 19 21 1 0 12 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 6 27 1 6 25 6 1 0 26 8 1 0 22 8 1 0 17 11 1 0 1 28 1 0 1 29 1 0 1 30 1 0 5 31 1 0 5 32 1 0 7 33 1 0 7 34 1 0 9 35 1 0 9 36 1 0 10 37 1 0 10 38 1 0 11 39 1 6 13 40 1 0 13 41 1 0 13 42 1 0 14 43 1 0 14 44 1 0 15 45 1 0 15 46 1 0 16 47 1 0 16 48 1 0 18 49 1 0 18 50 1 0 18 51 1 0 21 52 1 0 22 53 1 6 23 54 1 0 23 55 1 0 24 56 1 0 24 57 1 0 25 58 1 6 26 59 1 0 26 60 1 0 27 61 1 0 M END

Standard InCHIKey	JLYYLRJNDUJLOW-RWFJALSOSA-N
Standard InCHI	InChI=1S/C22H34O5/c1-14(23)27-13-22(26)12-21-10-7-16-19(2,17(21)6-5-15(22)11-21)8-4-9-20(16,3)18(24)25/h15-17,26H,4-13H2,1-3H3,(H,24,25)/t15-,16-,17-,19+,20+,21-,22+/m0/s1
SMILES	CC(=O)OC[C@@]1(C[C@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O)[C@@H]3CC[C@H]1C2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	378.24	Volume:	393.521 ? Van der Waals volume.
Dense:	0.961	LogP:	1.706 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.992 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.486 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.73	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.652	Fsp³:	0.909
MCE-18:	109.095 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.161	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.51	Promiscuous compounds:	0.405

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.258	MDCK Permeability:	-5.023
Pgp-inhibitor:	0.0	Pgp-substrate:	0.112
PAMPA:	0.999 ? 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%):	0.041	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.112

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021	MRP1:	0.946
Plasma Protein Binding (PPB):	71.225%	Volume Distribution (VD):	-0.06
Fu:	23.31% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.757	BCRP inhibitor:	0.013
BSEP inhibitor:	0.514

ADMET: Metabolism

CYP1A2-inhibitor:	0.4	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.056	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.977	CYP3A4-substrate:	0.044
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.0 ? 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):

1.104

Half-life (T1/2):

1.347

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.636	Drug-induced Liver Injury (DILI):	0.344
AMES Toxicity:	0.487	Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.328	Skin Sensitization:	0.992
Carcinogencity:	0.912	Eye Corrosion:	0.321
Eye Irritation:	0.891	Respiratory Toxicity:	0.699
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.444
Hematotoxicity:	0.619	Drug-induced Nephrotoxicity:	0.94
Genotoxicity:	0.329	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.086	Hek293 Cytotoxicity:	0.074
BCF:	0.756 ? 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:	3.814 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.497 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.569 ? 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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6333	Annona glabra	Species	Annonaceae	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
Inhibition	4
IC50	1
EC50	2

Activity Type	# Activity
Cell line	1
Organism	1
Non-molecular	4
Others	1

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
NPT759	Cell line	H9	Homo sapiens	IC50	=	65.0	ug.mL-1	PMID[9584397]
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	EC50	=	85.0	ug.mL-1	PMID[9584397]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.8	%	PMID[12398544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	30.1	%	PMID[12398544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	11.1	%	PMID[12398544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.0	%	PMID[12398544]
NPT27	Others	Unspecified	n.a.	EC50	=	0.8	ug.mL-1	PMID[9584397]

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 NPC480086 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	18106
0.1-0.2	28352
0.2-0.3	3119
0.3-0.4	208
0.4-0.5	56
0.5-0.6	11
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8621	High Similarity	NPC609700
0.746	Intermediate Similarity	NPC477936
0.6724	Remote Similarity	NPC180199
0.6724	Remote Similarity	NPC477919
0.6308	Remote Similarity	NPC477935
0.5714	Remote Similarity	NPC472853
0.5522	Remote Similarity	NPC480093
0.541	Remote Similarity	NPC268736
0.541	Remote Similarity	NPC252032
0.541	Remote Similarity	NPC319671
0.541	Remote Similarity	NPC477931
0.541	Remote Similarity	NPC476734
0.5312	Remote Similarity	NPC607026
0.5246	Remote Similarity	NPC330659
0.5246	Remote Similarity	NPC244708
0.5246	Remote Similarity	NPC161187

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5066
0.1-0.2	3997
0.2-0.3	86
0.3-0.4	0
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