NPASS Compound

Natural Product: NPC106625

Natural Product ID	NPC106625
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asebotin
IUPAC Name	1-[2-hydroxy-4-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Synonyms	Asebotin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL490513
PubChem CID	11190157
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

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 58 60 0 0 0 0 0 0 0 0999 V2000 -0.2876 -3.5129 -1.2448 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5854 -3.6343 -0.7891 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9860 -2.4623 0.1003 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8981 -1.2572 -0.5888 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8874 -0.2126 0.3819 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9404 1.0198 -0.1646 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2602 2.1314 -0.3253 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8723 3.1792 -1.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2492 4.3818 -1.2606 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8994 5.4017 -1.9774 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2052 6.6259 -2.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0240 4.5684 -0.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6701 3.5806 -0.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 2.3682 0.1394 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7936 1.3929 0.8933 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6737 1.4032 2.1418 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6985 0.4344 0.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3513 -0.4103 1.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2561 -1.3643 0.6437 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8003 -2.6075 0.2391 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7086 -3.4333 -0.3869 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9938 -3.0426 -0.5965 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4584 -1.7909 -0.1908 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5610 -0.9713 0.4293 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9077 -3.8762 -1.2275 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9709 3.7737 0.4335 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0414 -0.4876 1.3688 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0555 -1.3197 0.6134 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4483 -2.7119 0.4951 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5280 -3.3014 1.7519 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1441 -0.7689 -0.6761 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5709 -1.1696 2.4805 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 -4.3656 -1.5556 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3179 -3.7112 -1.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6560 -4.5763 -0.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3239 -2.4609 0.9876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9328 -0.3822 0.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8823 3.0463 -1.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0633 7.1352 -1.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7435 7.3077 -2.8407 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1831 6.4180 -2.5962 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5578 5.5139 -0.9253 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1085 -0.1931 -0.4457 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4889 0.9430 -0.3684 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9392 0.2479 1.9938 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5548 -0.9105 1.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7829 -2.8437 0.4367 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3720 -4.4053 -0.7091 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4635 -1.4604 -0.3439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8814 0.0002 0.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7806 -4.0384 -0.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2431 4.6183 0.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5476 0.4612 1.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0149 -1.3165 1.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9758 -3.2905 -0.2731 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2105 -2.8372 2.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7212 0.0363 -0.6623 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6671 -0.8625 2.7507 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 2 0 8 9 1 0 9 10 1 0 10 11 1 0 9 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 22 25 1 0 13 26 1 0 5 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 29 3 1 0 14 7 1 0 24 19 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 1 5 37 1 1 8 38 1 0 11 39 1 0 11 40 1 0 11 41 1 0 12 42 1 0 17 43 1 0 17 44 1 0 18 45 1 0 18 46 1 0 20 47 1 0 21 48 1 0 23 49 1 0 24 50 1 0 25 51 1 0 26 52 1 0 27 53 1 1 28 54 1 1 29 55 1 6 30 56 1 0 31 57 1 0 32 58 1 0 M END

Standard InCHIKey	PQCIBORQLVRFMR-MIUGBVLSSA-N
Standard InCHI	InChI=1S/C22H26O10/c1-30-13-8-15(26)18(14(25)7-4-11-2-5-12(24)6-3-11)16(9-13)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-3,5-6,8-9,17,19-24,26-29H,4,7,10H2,1H3/t17-,19-,20+,21-,22-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2cc(OC)cc(c2C(=O)CCc2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	450.15	Volume:	432.846 ? Van der Waals volume.
Dense:	1.04	LogP:	1.097 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.594 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.475 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	19.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	3.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.304	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.726	Fsp³:	0.409
MCE-18:	69.774 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.452	Fluc inhibitor:	0.374 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.164 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.627 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.082	Promiscuous compounds:	0.296

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.81	MDCK Permeability:	-4.966
Pgp-inhibitor:	0.086	Pgp-substrate:	0.038
PAMPA:	0.717 ? 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):	0.044
20% Bioavailability (F20%):	0.01	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.02
Plasma Protein Binding (PPB):	85.257%	Volume Distribution (VD):	-0.132
Fu:	15.358% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.246
BSEP inhibitor:	0.699

ADMET: Metabolism

CYP1A2-inhibitor:	0.623	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.039	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.45
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.764 ? 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):

3.461

Half-life (T1/2):

3.03

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.196
Human Hepatotoxicity (H-HT):	0.714	Drug-induced Liver Injury (DILI):	0.549
AMES Toxicity:	0.809	Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.047	Skin Sensitization:	0.99
Carcinogencity:	0.213	Eye Corrosion:	0.0
Eye Irritation:	0.281	Respiratory Toxicity:	0.04
Drug-induced Neurotoxicity:	0.051	Ototoxicity:	0.904
Hematotoxicity:	0.295	Drug-induced Nephrotoxicity:	0.71
Genotoxicity:	0.644	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.378	Hek293 Cytotoxicity:	0.477
BCF:	0.577 ? 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:	3.246 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.857 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.95 ? 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
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31809052]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[521818]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13961	Pieris japonica	Species	Ericaceae	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	8

Activity Type	# Activity
Non-molecular	8

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[521818]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	35.16	10'-3cpm	PMID[15787442]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	40.73	10'-3cpm	PMID[15787442]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	47.42	10'-3cpm	PMID[15787442]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	79.57	10'-3cpm	PMID[15787442]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	87.19	10'-3cpm	PMID[15787442]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	89.78	10'-3cpm	PMID[15787442]

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 NPC106625 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	16284
0.1-0.2	26701
0.2-0.3	5632
0.3-0.4	905
0.4-0.5	273
0.5-0.6	42
0.6-0.7	6
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
0.8529	High Similarity	NPC300537
0.7941	Intermediate Similarity	NPC259182
0.7727	Intermediate Similarity	NPC121001
0.7714	Intermediate Similarity	NPC6985
0.7143	Intermediate Similarity	NPC148273
0.7067	Intermediate Similarity	NPC127406
0.6986	Remote Similarity	NPC257963
0.6761	Remote Similarity	NPC99233
0.6571	Remote Similarity	NPC479374
0.64	Remote Similarity	NPC39351
0.6349	Remote Similarity	NPC18877
0.6269	Remote Similarity	NPC23084
0.5974	Remote Similarity	NPC219163
0.5897	Remote Similarity	NPC206378
0.5844	Remote Similarity	NPC308265
0.5802	Remote Similarity	NPC236934
0.5769	Remote Similarity	NPC127782
0.5658	Remote Similarity	NPC177742
0.5641	Remote Similarity	NPC97052
0.5625	Remote Similarity	NPC29830
0.5616	Remote Similarity	NPC199335
0.56	Remote Similarity	NPC604892
0.5584	Remote Similarity	NPC601828
0.5541	Remote Similarity	NPC190217
0.5429	Remote Similarity	NPC218685
0.5385	Remote Similarity	NPC606849
0.5316	Remote Similarity	NPC169248
0.5316	Remote Similarity	NPC72649
0.5309	Remote Similarity	NPC149244
0.5303	Remote Similarity	NPC144051
0.5278	Remote Similarity	NPC214910
0.5256	Remote Similarity	NPC57587
0.525	Remote Similarity	NPC88484
0.525	Remote Similarity	NPC163191
0.5231	Remote Similarity	NPC142319
0.5224	Remote Similarity	NPC28753
0.5224	Remote Similarity	NPC152722
0.52	Remote Similarity	NPC477240
0.5185	Remote Similarity	NPC471457
0.5185	Remote Similarity	NPC26195
0.5152	Remote Similarity	NPC217854
0.5143	Remote Similarity	NPC214454
0.5135	Remote Similarity	NPC106025
0.5128	Remote Similarity	NPC210192
0.5125	Remote Similarity	NPC271479
0.5122	Remote Similarity	NPC147596
0.5119	Remote Similarity	NPC472381
0.5075	Remote Similarity	NPC192810
0.5075	Remote Similarity	NPC286336
0.507	Remote Similarity	NPC215833
0.5068	Remote Similarity	NPC26653
0.5068	Remote Similarity	NPC80600
0.5062	Remote Similarity	NPC170475
0.506	Remote Similarity	NPC43638

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC106625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3937
0.1-0.2	4991
0.2-0.3	209
0.3-0.4	10
0.4-0.5	3
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