NPASS Compound

Natural Product: NPC246056

Natural Product ID	NPC246056
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bisnorstriatol
IUPAC Name	5-[14-(3,5-dihydroxyphenyl)tetradecyl]benzene-1,3-diol
Synonyms	Bisnorstriatol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL426392
PubChem CID	10431955
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

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 68 69 0 0 0 0 0 0 0 0999 V2000 -0.0098 1.7280 -1.0913 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5874 0.6672 -1.9293 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0288 -0.5684 -1.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0669 -0.3948 -0.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3390 0.1822 -0.7221 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3440 0.3259 0.3884 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6603 -0.9942 0.9907 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6845 -0.8922 2.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9232 -0.3187 1.5313 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1902 1.0266 1.4921 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3591 1.4972 0.9416 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3059 0.6491 0.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0200 -0.6987 0.4584 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8528 -1.1854 1.0068 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9705 -1.5863 -0.0780 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5884 2.8519 0.9219 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 1.5214 -0.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4749 1.1153 -0.8103 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5765 -0.1912 -1.4613 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8744 -0.5336 -2.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0821 -0.6872 -1.3038 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6843 0.4152 -0.5325 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9996 -0.1090 0.0770 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1796 0.0120 -0.6161 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3831 -0.4455 -0.1059 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3543 -1.0303 1.1301 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1887 -1.1753 1.8681 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0056 -0.7004 1.3137 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1742 -1.7711 3.1218 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5572 -0.3124 -0.8222 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 2.2795 -0.5147 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2841 2.5658 -1.8279 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5813 1.1344 -2.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0956 0.4541 -2.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5077 -1.2190 -2.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1725 -1.2128 -0.8964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2195 -1.4061 0.2669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7425 0.2515 0.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8054 -0.4834 -1.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1861 1.1615 -1.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9530 1.0422 1.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2755 0.7829 -0.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8156 -1.5518 1.3917 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1411 -1.6256 0.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3004 -0.2923 2.9582 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8928 -1.9251 2.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4508 1.7013 1.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2336 1.0311 -0.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6853 -2.2751 1.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6868 -2.2515 -0.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8501 3.5354 0.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9454 0.8574 0.6564 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3764 2.5182 0.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7398 1.9546 -1.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1716 1.2011 0.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -0.4513 -2.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4162 -0.9736 -0.6143 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0941 0.2308 -2.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7555 -1.4942 -2.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8775 -1.5313 -0.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9190 -1.1495 -1.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1682 0.7727 0.3561 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0129 1.2129 -1.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1494 0.4893 -1.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2755 -1.3999 1.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0524 -0.7849 1.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0464 -2.0296 3.5596 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6819 0.4832 -1.4617 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 11 16 1 0 1 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 25 30 1 0 14 9 1 0 28 23 1 0 1 31 1 0 1 32 1 0 2 33 1 0 2 34 1 0 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 10 47 1 0 12 48 1 0 14 49 1 0 15 50 1 0 16 51 1 0 17 52 1 0 17 53 1 0 18 54 1 0 18 55 1 0 19 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 24 64 1 0 26 65 1 0 28 66 1 0 29 67 1 0 30 68 1 0 M END

Standard InCHIKey	QUXULJDSRDXUCR-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C26H38O4/c27-23-15-21(16-24(28)19-23)13-11-9-7-5-3-1-2-4-6-8-10-12-14-22-17-25(29)20-26(30)18-22/h15-20,27-30H,1-14H2
SMILES	C(CCCCCCCc1cc(cc(c1)O)O)CCCCCCc1cc(cc(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	414.28	Volume:	460.481 ? Van der Waals volume.
Dense:	0.9	LogP:	6.61 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.763 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.345 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	12.0
TPSA:	80.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.237	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.015	Fsp³:	0.538
MCE-18:	12.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.967	Fluc inhibitor:	0.455 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.06 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.66	Promiscuous compounds:	0.09

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.267	MDCK Permeability:	-4.767
Pgp-inhibitor:	0.001	Pgp-substrate:	0.005
PAMPA:	0.003 ? 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):	0.0
20% Bioavailability (F20%):	0.945	30% Bioavailability (F30%):	0.976
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025	MRP1:	0.479
Plasma Protein Binding (PPB):	99.338%	Volume Distribution (VD):	1.33
Fu:	0.862% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.965
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.732
BSEP inhibitor:	0.466

ADMET: Metabolism

CYP1A2-inhibitor:	0.946	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.301	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.991	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.056	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.006	CYP2C8-inhibitor:	1.0
HLM stability:	0.966 ? 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):

2.413

Half-life (T1/2):

2.028

ADMET: Toxicity

hERG Blockers:	0.829	hERG Blockers (10um):	0.934
Human Hepatotoxicity (H-HT):	0.545	Drug-induced Liver Injury (DILI):	0.041
AMES Toxicity:	0.127	Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.848	Skin Sensitization:	0.994
Carcinogencity:	0.185	Eye Corrosion:	0.585
Eye Irritation:	0.999	Respiratory Toxicity:	0.893
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.144
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.043
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.932	Hek293 Cytotoxicity:	0.968
BCF:	1.293 ? 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:	5.14 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.262 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.063 ? 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
NPO8932	Panopsis rubescens	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096862]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8932	Panopsis rubescens	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8932	Panopsis rubescens	Species	Proteaceae	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	2
IC50	4

Activity Type	# Activity
Individual protein	3
Cell line	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	79.0	%	PMID[24359277]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	50.0	%	PMID[24601675]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	IC50	=	5800.0	nM	PMID[11575942]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	29200.0	nM	PMID[22834923]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	28800.0	nM	PMID[25221651]
NPT395	Cell line	SF-268	Homo sapiens	IC50	=	29800.0	nM	PMID[24168147]

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 NPC246056 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	32688
0.1-0.2	15446
0.2-0.3	1468
0.3-0.4	140
0.4-0.5	55
0.5-0.6	24
0.6-0.7	9
0.7-0.8	0
0.8-0.85	8
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC294186
0.8889	High Similarity	NPC147310
0.8889	High Similarity	NPC137415
0.8889	High Similarity	NPC166313
0.8889	High Similarity	NPC192032
0.8889	High Similarity	NPC24407
0.8889	High Similarity	NPC11280
0.8	Intermediate Similarity	NPC470700
0.8	Intermediate Similarity	NPC54844
0.8	Intermediate Similarity	NPC39097
0.8	Intermediate Similarity	NPC302681
0.8	Intermediate Similarity	NPC241891
0.8	Intermediate Similarity	NPC118286
0.8	Intermediate Similarity	NPC134829
0.8	Intermediate Similarity	NPC109691
0.75	Intermediate Similarity	NPC53051
0.75	Intermediate Similarity	NPC24404
0.75	Intermediate Similarity	NPC313030
0.75	Intermediate Similarity	NPC39664
0.7273	Intermediate Similarity	NPC146798
0.7273	Intermediate Similarity	NPC222522
0.7273	Intermediate Similarity	NPC106396
0.7273	Intermediate Similarity	NPC94351
0.7273	Intermediate Similarity	NPC168303
0.7059	Intermediate Similarity	NPC486908
0.6667	Remote Similarity	NPC71002
0.6667	Remote Similarity	NPC10588
0.6667	Remote Similarity	NPC302219
0.6667	Remote Similarity	NPC242342
0.6667	Remote Similarity	NPC249828
0.6667	Remote Similarity	NPC85479
0.6667	Remote Similarity	NPC284011
0.6486	Remote Similarity	NPC114064
0.6486	Remote Similarity	NPC72947
0.5882	Remote Similarity	NPC76938
0.5882	Remote Similarity	NPC3358
0.5882	Remote Similarity	NPC32714
0.5882	Remote Similarity	NPC306884
0.5882	Remote Similarity	NPC603092
0.5789	Remote Similarity	NPC115808
0.5758	Remote Similarity	NPC59506
0.5714	Remote Similarity	NPC486909
0.5588	Remote Similarity	NPC488411
0.5588	Remote Similarity	NPC488410
0.5588	Remote Similarity	NPC488409
0.5581	Remote Similarity	NPC305603
0.5581	Remote Similarity	NPC61033
0.5581	Remote Similarity	NPC127894
0.5581	Remote Similarity	NPC470759
0.5526	Remote Similarity	NPC166761
0.5455	Remote Similarity	NPC123273
0.5455	Remote Similarity	NPC318325
0.5294	Remote Similarity	NPC37802
0.5128	Remote Similarity	NPC483454
0.5128	Remote Similarity	NPC162314
0.5116	Remote Similarity	NPC470760
0.5106	Remote Similarity	NPC123559
0.5106	Remote Similarity	NPC140521

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC246056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6735
0.1-0.2	2291
0.2-0.3	110
0.3-0.4	12
0.4-0.5	2
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