NPASS Compound

Natural Product: NPC480783

Natural Product ID	NPC480783
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BOUBPFYATGCWDW-ABZBRZROSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10437493
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

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 75 79 0 0 0 0 0 0 0 0999 V2000 -6.2577 -2.7527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5298 -1.9578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3247 -3.2299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7349 -0.6857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2358 -0.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4410 0.5340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1452 1.8584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9419 0.4816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1470 1.7537 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 0.3943 1.2135 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 O 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 0.3273 -0.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1683 -0.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5090 0.2098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9356 0.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6237 -0.7939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2475 2.1406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1328 3.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7062 2.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4086 3.6844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8351 3.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9499 4.2246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6741 2.6041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7888 1.6004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4769 0.1332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7057 -0.7271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0503 -0.3303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7545 -1.6548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9859 4.0713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5447 -2.7444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2742 -2.7784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2458 -1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4547 -3.1171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6161 -1.0216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8297 -1.9033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4391 0.6387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8916 -4.1122 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6238 -1.3932 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9857 -3.5476 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8019 -1.1629 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5968 -2.4350 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1590 -4.1739 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1196 -4.5020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8730 -2.1936 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5378 2.3156 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2143 -0.1736 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1147 1.2436 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1147 -1.2436 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4658 -3.1740 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5991 -1.9587 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7438 -1.2717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7727 -1.7582 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4259 -1.6968 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6762 -2.2929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5593 3.6078 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5952 4.5447 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0562 4.3263 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8369 4.1750 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2154 2.0639 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4404 -1.7007 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2361 -1.8895 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4531 3.7595 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6378 4.7290 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2978 5.5385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5350 -3.8537 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7678 -2.6397 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8527 -0.8062 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9480 -3.1168 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7938 -3.0524 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7636 -0.0655 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1147 1.3429 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1433 1.9631 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 20 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 26 32 1 0 16 33 1 0 15 34 1 0 14 35 1 1 35 36 2 0 35 37 1 0 37 38 1 0 4 39 1 0 24 9 1 0 14 10 1 0 30 18 1 0 22 11 1 0 17 11 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 3 44 1 0 3 45 1 0 3 46 1 0 5 47 1 0 9 48 1 6 10 49 1 1 12 50 1 0 12 51 1 0 15 52 1 1 16 53 1 1 17 54 1 6 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 6 21 59 1 0 21 60 1 0 22 61 1 1 27 62 1 0 30 63 1 6 31 64 1 0 32 65 1 0 32 66 1 0 32 67 1 0 33 68 1 0 34 69 1 0 38 70 1 0 38 71 1 0 38 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 M END

Standard InCHIKey	BOUBPFYATGCWDW-ABZBRZROSA-N
Standard InCHI	InChI=1S/C28H36O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h7-8,11,14,16,18-23,31-33H,9-10H2,1-6H3/b12-8+/t14-,16+,18+,19+,20+,21+,22+,23-,26-,27+,28+/m0/s1
SMILES	CC(C)/C(=C/C(=O)O[C@@H]1[C@@H]2[C@]34CO[C@]2([C@H]([C@@H]([C@@H]4[C@]2(C)[C@@H](C[C@H]3OC1=O)C(=CC(=O)[C@H]2O)C)O)O)C(=O)OC)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	548.23	Volume:	530.935 ? Van der Waals volume.
Dense:	1.033	LogP:	1.371 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.853 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.721 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	28.0
TPSA:	165.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.25	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.627	Fsp³:	0.714
MCE-18:	138.125 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.613	Fluc inhibitor:	0.02 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? 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:	0.083	Promiscuous compounds:	0.332

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.767	MDCK Permeability:	-5.239
Pgp-inhibitor:	0.708	Pgp-substrate:	0.929
PAMPA:	0.247 ? 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):	0.008
20% Bioavailability (F20%):	0.213	30% Bioavailability (F30%):	0.895
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	66.955%	Volume Distribution (VD):	-0.277
Fu:	32.858% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.002
BSEP inhibitor:	0.907

ADMET: Metabolism

CYP1A2-inhibitor:	0.064	CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.256	CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.737
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.97
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.84
HLM stability:	0.353 ? 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):

3.676

Half-life (T1/2):

2.643

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.099
Human Hepatotoxicity (H-HT):	0.881	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.761	Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.816	Skin Sensitization:	1.0
Carcinogencity:	0.624	Eye Corrosion:	0.008
Eye Irritation:	0.667	Respiratory Toxicity:	0.7
Drug-induced Neurotoxicity:	0.852	Ototoxicity:	0.703
Hematotoxicity:	0.56	Drug-induced Nephrotoxicity:	0.975
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.271
A549 Cytotoxicity:	0.256	Hek293 Cytotoxicity:	0.527
BCF:	0.636 ? 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:	3.437 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.326 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.641 ? 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
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2089121]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379416]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3443857]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3760882]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3841557]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288443]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8133299]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	PMID[8133299]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691212]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	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
ED50	6

Activity Type	# Activity
Cell line	6

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
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.08	ug ml-1	PMID[8133299]
NPT81	Cell line	A549	Homo sapiens	ED50	=	0.55	ug ml-1	PMID[8133299]
NPT180	Cell line	HCT-8	Homo sapiens	ED50	=	0.09	ug ml-1	PMID[8133299]
NPT168	Cell line	P388	Mus musculus	ED50	=	0.09	ug ml-1	PMID[8133299]
NPT672	Cell line	TE-671	Homo sapiens	ED50	=	0.08	ug ml-1	PMID[8133299]
NPT1091	Cell line	RPMI-7951	Homo sapiens	ED50	=	0.09	ug ml-1	PMID[8133299]

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 NPC480783 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	17036
0.1-0.2	31134
0.2-0.3	1571
0.3-0.4	41
0.4-0.5	32
0.5-0.6	18
0.6-0.7	18
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8806	High Similarity	NPC17772
0.8514	High Similarity	NPC480777
0.8429	Intermediate Similarity	NPC485623
0.7403	Intermediate Similarity	NPC480784
0.7089	Intermediate Similarity	NPC265557
0.6962	Remote Similarity	NPC480785
0.6962	Remote Similarity	NPC67251
0.68	Remote Similarity	NPC470776
0.675	Remote Similarity	NPC480787
0.6667	Remote Similarity	NPC40632
0.6579	Remote Similarity	NPC213084
0.65	Remote Similarity	NPC18945
0.65	Remote Similarity	NPC152301
0.6494	Remote Similarity	NPC96312
0.6494	Remote Similarity	NPC328374
0.6456	Remote Similarity	NPC251236
0.6329	Remote Similarity	NPC479018
0.6235	Remote Similarity	NPC480786
0.619	Remote Similarity	NPC476729
0.6173	Remote Similarity	NPC146432
0.6173	Remote Similarity	NPC470778
0.6125	Remote Similarity	NPC89929
0.6024	Remote Similarity	NPC190185
0.5977	Remote Similarity	NPC105926
0.5875	Remote Similarity	NPC143268
0.5783	Remote Similarity	NPC24651
0.5732	Remote Similarity	NPC323821
0.5698	Remote Similarity	NPC94509
0.5698	Remote Similarity	NPC479017
0.5684	Remote Similarity	NPC479019
0.5682	Remote Similarity	NPC470779
0.5663	Remote Similarity	NPC16081
0.5625	Remote Similarity	NPC480779
0.5595	Remote Similarity	NPC476008
0.5513	Remote Similarity	NPC49451
0.5417	Remote Similarity	NPC262813
0.5301	Remote Similarity	NPC470777
0.5208	Remote Similarity	NPC190065
0.52	Remote Similarity	NPC251998
0.5102	Remote Similarity	NPC141215
0.5062	Remote Similarity	NPC97908

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6550
0.1-0.2	2573
0.2-0.3	27
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