NPASS Compound

Natural Product: NPC476094

Natural Product ID	NPC476094
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ULVXABAIWWZKTL-FAGROPTLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL525942
PubChem CID	44561296
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 80 84 0 0 0 0 0 0 0 0999 V2000 1.3640 -2.3224 -2.0613 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7665 -2.7950 -0.7874 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7610 -3.0380 0.3278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9121 -1.9102 1.2569 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4888 -0.5424 0.8114 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1440 -0.5316 0.0887 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2827 -1.8805 -0.1821 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5707 -1.9640 -0.9626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 -1.7091 0.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4118 -0.2486 0.4889 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9108 0.0841 1.2817 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8437 1.3396 0.9153 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3623 2.4015 0.3499 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4831 2.3370 -0.1684 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7166 3.7116 0.2736 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4927 3.9699 0.8695 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0766 5.2270 0.7634 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4289 6.2181 0.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7776 5.9851 -0.5515 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3248 4.7246 -0.4232 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3283 0.0929 1.3243 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3192 0.7083 1.8719 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8146 1.6541 1.2166 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9089 0.3932 3.1867 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8807 -2.6491 1.2155 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5325 -2.5102 1.0650 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4015 -2.5398 2.6168 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3403 -4.0479 0.7348 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7677 -3.1599 -1.6291 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0687 -3.2225 -3.0057 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1481 -2.1092 -3.5825 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2832 -4.4482 -3.7666 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2044 0.5054 -0.9162 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4955 0.1506 0.1034 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2415 1.1937 0.5985 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9694 1.4861 1.7619 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2642 1.8869 -0.1971 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9545 2.9227 0.3890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9361 3.6334 -0.2924 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2354 3.2962 -1.5980 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5381 2.2532 -2.1817 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5549 1.5428 -1.4987 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2962 -1.7337 -1.8851 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6399 -1.8318 -2.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7283 -3.2209 -2.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2255 -3.7462 -1.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3670 -3.9449 0.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6967 -3.4186 -0.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0119 -1.8069 1.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4366 -2.1477 2.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3937 0.0290 1.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6971 -1.1156 -1.6615 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5347 -1.9709 -0.0121 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2412 0.2412 -0.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9912 -0.8169 1.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0152 3.2274 1.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0259 5.4802 1.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8715 7.2040 -0.0409 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3220 6.7209 -1.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2978 4.5611 -0.9175 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8588 0.9463 3.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2112 0.5127 4.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2313 -0.6902 3.2151 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7589 -2.0501 3.3467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4365 -2.1296 2.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5593 -3.5693 3.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1911 -3.9771 0.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7343 -4.6559 1.5957 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5021 -4.6440 0.3508 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6296 -5.3094 -3.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0729 -4.2154 -4.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3806 -4.7840 -4.3303 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6727 0.8714 -1.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0292 0.2937 -1.7059 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7060 1.3994 -0.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7133 3.1761 1.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4672 4.4430 0.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9970 3.8404 -2.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7993 2.0150 -3.2107 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0202 0.7285 -1.9767 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 10 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 9 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 8 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 6 33 1 0 5 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 7 2 1 0 11 6 1 0 26 7 1 0 20 15 1 0 42 37 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 8 52 1 0 9 53 1 0 10 54 1 0 11 55 1 0 16 56 1 0 17 57 1 0 18 58 1 0 19 59 1 0 20 60 1 0 24 61 1 0 24 62 1 0 24 63 1 0 27 64 1 0 27 65 1 0 27 66 1 0 28 67 1 0 28 68 1 0 28 69 1 0 32 70 1 0 32 71 1 0 32 72 1 0 33 73 1 0 33 74 1 0 33 75 1 0 38 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 M END

Standard InCHIKey	ULVXABAIWWZKTL-FAGROPTLSA-N
Standard InCHI	InChI=1S/C33H38O9/c1-19-17-18-24(40-29(36)22-13-9-7-10-14-22)32(6)28(41-30(37)23-15-11-8-12-16-23)26(38-20(2)34)25-27(39-21(3)35)33(19,32)42-31(25,4)5/h7-16,19,24-28H,17-18H2,1-6H3/t19-,24+,25-,26-,27-,28-,32+,33-/m1/s1
SMILES	CC1CCC(C2(C13C(C(C(C2OC(=O)C4=CC=CC=C4)OC(=O)C)C(O3)(C)C)OC(=O)C)C)OC(=O)C5=CC=CC=C5

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.25	Volume:	589.289 ? Van der Waals volume.
Dense:	0.981	LogP:	4.28 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.633 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.971 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	114.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.348	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.573	Fsp³:	0.515
MCE-18:	159.84 ? 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:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.413	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.53 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.213	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.981	MDCK Permeability:	-4.622
Pgp-inhibitor:	1.0	Pgp-substrate:	0.176
PAMPA:	0.289 ? 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%):	0.106	30% Bioavailability (F30%):	0.601
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045	MRP1:	1.0
Plasma Protein Binding (PPB):	97.016%	Volume Distribution (VD):	-0.28
Fu:	2.546% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.652
OATP1B3 inhibitor:	0.826	BCRP inhibitor:	0.038
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.155
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.972

Half-life (T1/2):

0.905

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.775
Human Hepatotoxicity (H-HT):	0.02	Drug-induced Liver Injury (DILI):	0.759
AMES Toxicity:	0.065	Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.089	Skin Sensitization:	0.376
Carcinogencity:	0.321	Eye Corrosion:	0.0
Eye Irritation:	0.146	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.489	Ototoxicity:	0.525
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.038
Genotoxicity:	0.015	RPMI-8226 Immunitoxicity:	0.029
A549 Cytotoxicity:	0.024	Hek293 Cytotoxicity:	0.511
BCF:	1.253 ? 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:	4.281 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.107 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.69 ? 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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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
Activity	1

Activity Type	# Activity
Cell line	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
NPT116	Cell line	HL-60	Homo sapiens	Activity	<	50.0	%	PMID[20022253]

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 NPC476094 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	16166
0.1-0.2	31757
0.2-0.3	1413
0.3-0.4	354
0.4-0.5	78
0.5-0.6	56
0.6-0.7	18
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC475429
0.9286	High Similarity	NPC66761
0.9286	High Similarity	NPC483843
0.8621	High Similarity	NPC211137
0.8387	Intermediate Similarity	NPC473758
0.7536	Intermediate Similarity	NPC212768
0.75	Intermediate Similarity	NPC90257
0.75	Intermediate Similarity	NPC69357
0.7143	Intermediate Similarity	NPC481047
0.7143	Intermediate Similarity	NPC481045
0.7042	Intermediate Similarity	NPC4421
0.697	Remote Similarity	NPC483845
0.6912	Remote Similarity	NPC483844
0.6667	Remote Similarity	NPC90614
0.662	Remote Similarity	NPC483848
0.6562	Remote Similarity	NPC183122
0.6562	Remote Similarity	NPC474608
0.6418	Remote Similarity	NPC475759
0.6418	Remote Similarity	NPC483862
0.6338	Remote Similarity	NPC609924
0.6308	Remote Similarity	NPC283375
0.6301	Remote Similarity	NPC483849
0.6087	Remote Similarity	NPC473060
0.6081	Remote Similarity	NPC481050
0.6026	Remote Similarity	NPC473115
0.6	Remote Similarity	NPC483887
0.6	Remote Similarity	NPC158020
0.6	Remote Similarity	NPC163719
0.6	Remote Similarity	NPC95810
0.5942	Remote Similarity	NPC483847
0.5921	Remote Similarity	NPC603877
0.5867	Remote Similarity	NPC609221
0.5857	Remote Similarity	NPC483886
0.5797	Remote Similarity	NPC118080
0.5775	Remote Similarity	NPC48017
0.5775	Remote Similarity	NPC200471
0.5775	Remote Similarity	NPC472575
0.5735	Remote Similarity	NPC473081
0.5735	Remote Similarity	NPC195647
0.5735	Remote Similarity	NPC301556
0.5714	Remote Similarity	NPC241951
0.5714	Remote Similarity	NPC470152
0.5694	Remote Similarity	NPC147217
0.5694	Remote Similarity	NPC137718
0.5694	Remote Similarity	NPC148062
0.5676	Remote Similarity	NPC57628
0.5676	Remote Similarity	NPC479043
0.5634	Remote Similarity	NPC17877
0.5634	Remote Similarity	NPC51314
0.5556	Remote Similarity	NPC246480
0.5556	Remote Similarity	NPC147880
0.5513	Remote Similarity	NPC608007
0.5507	Remote Similarity	NPC200592
0.5507	Remote Similarity	NPC270498
0.5507	Remote Similarity	NPC610542
0.5479	Remote Similarity	NPC483842
0.5467	Remote Similarity	NPC252314
0.5455	Remote Similarity	NPC481065
0.5441	Remote Similarity	NPC147561
0.5417	Remote Similarity	NPC281717
0.5405	Remote Similarity	NPC473088
0.5395	Remote Similarity	NPC210591
0.5342	Remote Similarity	NPC246841
0.5342	Remote Similarity	NPC483883
0.5342	Remote Similarity	NPC151585
0.5325	Remote Similarity	NPC475652
0.5263	Remote Similarity	NPC481059
0.525	Remote Similarity	NPC479040
0.525	Remote Similarity	NPC488899
0.5244	Remote Similarity	NPC483864
0.5205	Remote Similarity	NPC163087
0.519	Remote Similarity	NPC475039
0.5185	Remote Similarity	NPC125106
0.5185	Remote Similarity	NPC472573
0.5185	Remote Similarity	NPC610927
0.5132	Remote Similarity	NPC306146
0.5132	Remote Similarity	NPC483841
0.5125	Remote Similarity	NPC475122
0.5122	Remote Similarity	NPC301368
0.5122	Remote Similarity	NPC84815
0.507	Remote Similarity	NPC100913
0.5067	Remote Similarity	NPC483846
0.5067	Remote Similarity	NPC472572
0.5065	Remote Similarity	NPC472569
0.5065	Remote Similarity	NPC16912

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4062
0.1-0.2	4903
0.2-0.3	185
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