NPASS Compound

Natural Product: NPC73781

Natural Product ID	NPC73781
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PYLYQTVVQXPBIJ-OUZJQUPYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46173976
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 71 75 0 0 0 0 0 0 0 0999 V2000 -8.0529 2.9138 0.7484 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5781 1.6140 0.7605 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7950 0.4500 0.7191 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4081 0.5308 0.6565 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6166 -0.5982 0.6138 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2830 -1.8265 0.6373 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 -1.9268 0.6987 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4262 -0.7671 0.7407 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8091 -0.8767 0.8027 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1439 -0.5617 0.5193 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6348 -0.6874 -0.8731 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1072 -0.6381 -0.9240 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4470 -1.8715 -0.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0303 -1.6504 -0.5465 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7874 -1.0774 0.4460 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1594 -0.8748 0.3091 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2084 -0.2959 1.1835 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7138 0.7871 2.0830 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7268 0.3706 2.9389 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2118 0.1911 0.1675 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5551 0.3988 0.7102 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3247 -0.5866 1.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5811 -0.2829 1.7275 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0983 1.0034 1.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3189 2.0013 1.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0708 1.6965 0.6489 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8614 3.2919 1.0696 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1640 4.3751 0.5310 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3653 1.2949 2.1494 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1764 -0.9394 -0.7323 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8022 -1.2512 -0.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0543 -1.8288 -1.8532 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6992 -2.0253 -1.7101 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6936 -2.2083 -3.0153 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1287 -2.7975 -4.1372 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8966 -0.3815 -2.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9268 0.5766 -2.6895 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9711 0.4151 -1.7849 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9939 1.1308 -1.8102 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1747 3.0110 0.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7848 3.2833 1.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8161 3.6372 0.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9708 1.5049 0.6582 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7005 -2.7312 0.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1865 -2.8615 0.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3002 -0.3327 1.5163 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7169 0.3324 1.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7254 -1.4306 1.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9348 -1.6830 -1.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8062 0.2790 -0.3774 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7018 -2.0006 0.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7261 -2.7194 -1.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3039 -0.7737 1.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6678 -1.1492 1.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5894 1.1165 2.7032 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4313 1.6536 1.4759 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0779 0.1724 3.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8119 1.0703 -0.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9488 -1.5980 1.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1722 -1.1025 2.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4734 2.4916 0.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8757 5.1865 0.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6113 4.0663 -0.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4473 4.7945 1.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1591 1.0926 1.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0708 -2.4738 -2.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7829 -3.5783 -4.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0749 -1.9968 -4.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1230 -3.1979 -4.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9487 0.1161 -2.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1219 -1.2666 -3.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 24 29 1 0 20 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 12 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 8 3 1 0 38 11 1 0 33 14 1 0 31 16 2 0 26 21 1 0 1 40 1 0 1 41 1 0 1 42 1 0 4 43 1 0 6 44 1 0 7 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 6 12 50 1 1 13 51 1 0 13 52 1 0 15 53 1 0 17 54 1 1 18 55 1 0 18 56 1 0 19 57 1 0 20 58 1 6 22 59 1 0 23 60 1 0 26 61 1 0 28 62 1 0 28 63 1 0 28 64 1 0 29 65 1 0 33 66 1 0 35 67 1 0 35 68 1 0 35 69 1 0 36 70 1 0 36 71 1 0 M END

Standard InCHIKey	PYLYQTVVQXPBIJ-OUZJQUPYSA-N
Standard InCHI	InChI=1S/C30H32O9/c1-35-25-11-16(4-6-23(25)32)9-20-19(15-38-30(20)34)8-17-10-21-22(14-31)28(39-29(21)27(12-17)37-3)18-5-7-24(33)26(13-18)36-2/h4-7,10-13,19-20,22,28,31-33H,8-9,14-15H2,1-3H3/t19-,20+,22-,28+/m0/s1
SMILES	COc1cc(ccc1O)C[C@@H]1[C@@H](Cc2cc3[C@H](CO)[C@@H](c4ccc(c(c4)OC)O)Oc3c(c2)OC)COC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.2	Volume:	537.401 ? Van der Waals volume.
Dense:	0.998	LogP:	2.66 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.491 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.075 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	28.0
TPSA:	123.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.349	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.062	Fsp³:	0.367
MCE-18:	97.317 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.821	Fluc inhibitor:	0.339 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? 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:	0.083	Promiscuous compounds:	0.179

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.124	MDCK Permeability:	-4.819
Pgp-inhibitor:	0.658	Pgp-substrate:	0.168
PAMPA:	0.011 ? 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):	0.004
20% Bioavailability (F20%):	0.823	30% Bioavailability (F30%):	0.945
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.913
Plasma Protein Binding (PPB):	92.238%	Volume Distribution (VD):	-0.131
Fu:	7.939% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.404
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.992
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.276 ? 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):

4.076

Half-life (T1/2):

2.49

ADMET: Toxicity

hERG Blockers:	0.126	hERG Blockers (10um):	0.454
Human Hepatotoxicity (H-HT):	0.974	Drug-induced Liver Injury (DILI):	0.931
AMES Toxicity:	0.845	Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.72	Skin Sensitization:	0.985
Carcinogencity:	0.607	Eye Corrosion:	0.0
Eye Irritation:	0.695	Respiratory Toxicity:	0.169
Drug-induced Neurotoxicity:	0.569	Ototoxicity:	0.891
Hematotoxicity:	0.727	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.332
A549 Cytotoxicity:	0.792	Hek293 Cytotoxicity:	0.799
BCF:	1.166 ? 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:	3.93 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.214 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.68 ? 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
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	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

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

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 NPC73781 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	20346
0.1-0.2	26540
0.2-0.3	2495
0.3-0.4	312
0.4-0.5	120
0.5-0.6	33
0.6-0.7	13
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	Natural Product ID
0.6418	Remote Similarity	NPC68779
0.6418	Remote Similarity	NPC108598
0.6389	Remote Similarity	NPC29799
0.6389	Remote Similarity	NPC263367
0.6389	Remote Similarity	NPC54743
0.6338	Remote Similarity	NPC106920
0.6338	Remote Similarity	NPC300776
0.6338	Remote Similarity	NPC15811
0.6338	Remote Similarity	NPC176814
0.6338	Remote Similarity	NPC4982
0.6338	Remote Similarity	NPC606629
0.6164	Remote Similarity	NPC177160
0.6056	Remote Similarity	NPC273657
0.5921	Remote Similarity	NPC282291
0.5921	Remote Similarity	NPC166137
0.5844	Remote Similarity	NPC216223
0.5823	Remote Similarity	NPC478703
0.5823	Remote Similarity	NPC478704
0.5753	Remote Similarity	NPC300757
0.5641	Remote Similarity	NPC206413
0.5641	Remote Similarity	NPC482649
0.5641	Remote Similarity	NPC149003
0.5641	Remote Similarity	NPC482647
0.5641	Remote Similarity	NPC482648
0.5641	Remote Similarity	NPC482651
0.5641	Remote Similarity	NPC194244
0.5641	Remote Similarity	NPC482650
0.5455	Remote Similarity	NPC472961
0.5455	Remote Similarity	NPC472962
0.5444	Remote Similarity	NPC224674
0.5444	Remote Similarity	NPC64475
0.5385	Remote Similarity	NPC284881
0.5385	Remote Similarity	NPC93433
0.5385	Remote Similarity	NPC474444
0.5341	Remote Similarity	NPC299706
0.5341	Remote Similarity	NPC115466
0.5341	Remote Similarity	NPC61604
0.5325	Remote Similarity	NPC156502
0.5325	Remote Similarity	NPC10737
0.525	Remote Similarity	NPC253878
0.525	Remote Similarity	NPC471414
0.5195	Remote Similarity	NPC100675
0.5195	Remote Similarity	NPC601691
0.5122	Remote Similarity	NPC163898
0.5065	Remote Similarity	NPC5310
0.5065	Remote Similarity	NPC610652

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC73781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3901
0.1-0.2	5148
0.2-0.3	97
0.3-0.4	4
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