NPASS Compound

Natural Product: NPC309320

Natural Product ID	NPC309320
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ODIUJYWRAXKUON-JTGGKBNKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102148063
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 79 82 0 0 0 0 0 0 0 0999 V2000 12.1177 0.9684 0.9085 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2162 -0.3390 0.3873 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0574 -0.9641 -0.0379 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7966 -0.3723 0.0224 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6476 -0.9697 -0.3886 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7638 -2.2683 -0.9042 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9781 -2.9004 -0.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1146 -2.2427 -0.5539 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3512 -2.8667 -0.6304 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3329 -0.3507 -0.3249 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1085 0.8546 0.1234 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7739 1.4486 0.1748 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6545 2.6122 0.6135 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6351 0.7786 -0.2393 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3320 1.3486 -0.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3483 0.3089 -0.6933 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3733 -0.9228 0.2020 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5125 -0.5635 1.2480 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3566 -0.0917 0.5585 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9160 0.7351 -0.5446 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1895 0.4782 -1.7203 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4054 0.6619 1.4235 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6069 0.1809 1.8015 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5769 -0.0010 0.6593 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6963 1.1946 -0.2198 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7351 2.2016 0.1876 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6965 1.6323 1.1926 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9177 0.1776 0.8438 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8780 -0.2948 1.7351 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9980 -0.8251 1.1845 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7866 0.1498 0.3476 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0067 -0.5357 -0.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1735 -0.5170 0.4884 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2835 -1.1631 -0.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2124 -1.7976 -1.2589 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0200 -1.7969 -1.9473 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9130 -1.1673 -1.4330 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3188 -2.4434 -1.8010 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7674 -0.5288 1.1076 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8864 2.3623 1.1748 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1996 3.4271 0.5741 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8723 0.7816 -1.5507 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6461 -0.0241 -1.9930 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0876 1.3337 1.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7501 1.6055 0.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3281 0.9750 1.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7718 0.6274 0.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8811 -2.7773 -1.2414 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0727 -3.8968 -1.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6982 -3.4173 0.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4627 -0.9141 -0.6672 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9439 1.4266 0.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1398 1.6209 0.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2808 2.2592 -0.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9545 -1.7882 -0.3419 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3833 -1.1985 0.5404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1484 -1.0205 0.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8371 1.8233 -0.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0888 1.3514 -2.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5341 -0.7513 2.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0793 0.9673 2.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1299 -0.8168 0.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7278 1.7479 -0.2009 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3535 2.4223 -0.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3159 1.7186 2.2342 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2153 0.0758 -0.2209 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7150 -1.2230 1.9422 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7039 -1.7183 0.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1460 0.5266 -0.4564 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2050 0.9505 1.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3080 -0.0349 1.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2445 -1.1809 0.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9974 -2.3053 -2.8974 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9981 -1.1889 -1.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1570 -2.6745 -1.2780 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7970 3.2325 1.6311 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9391 3.9633 -0.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4907 -0.1300 -1.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2543 0.6023 -2.6617 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 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 35 38 1 0 28 39 1 0 27 40 1 0 26 41 1 0 25 42 1 0 16 43 1 6 8 3 1 0 20 16 1 0 39 24 1 0 37 32 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 6 48 1 0 7 49 1 0 9 50 1 0 10 51 1 0 11 52 1 0 15 53 1 0 15 54 1 0 17 55 1 0 17 56 1 0 19 57 1 6 20 58 1 1 21 59 1 0 23 60 1 0 23 61 1 0 24 62 1 6 25 63 1 6 26 64 1 6 27 65 1 1 28 66 1 6 30 67 1 0 30 68 1 0 31 69 1 0 31 70 1 0 33 71 1 0 34 72 1 0 36 73 1 0 37 74 1 0 38 75 1 0 40 76 1 0 41 77 1 0 42 78 1 0 43 79 1 0 M END

Standard InCHIKey	ODIUJYWRAXKUON-JTGGKBNKSA-N
Standard InCHI	InChI=1S/C29H36O14/c1-38-20-12-17(4-8-19(20)31)5-9-22(32)41-14-29(37)15-42-28(26(29)36)40-13-21-23(33)24(34)25(35)27(43-21)39-11-10-16-2-6-18(30)7-3-16/h2-9,12,21,23-28,30-31,33-37H,10-11,13-15H2,1H3/b9-5+/t21-,23-,24+,25-,26+,27-,28-,29-/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC[C@]1(CO[C@H]([C@@H]1O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](OCCc2ccc(cc2)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.21	Volume:	577.886 ? Van der Waals volume.
Dense:	1.052	LogP:	0.899 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.321 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.521 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	25.0
TPSA:	214.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.116	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.605	Fsp³:	0.483
MCE-18:	95.721 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.659	Fluc inhibitor:	0.669 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.12 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.61 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.07	Promiscuous compounds:	0.323

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.313	MDCK Permeability:	-5.318
Pgp-inhibitor:	0.0	Pgp-substrate:	0.523
PAMPA:	0.994 ? 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):	0.845
20% Bioavailability (F20%):	0.927	30% Bioavailability (F30%):	0.968
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.003
Plasma Protein Binding (PPB):	76.419%	Volume Distribution (VD):	-0.301
Fu:	24.807% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.464
BSEP inhibitor:	0.67

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.922 ? 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):

1.664

Half-life (T1/2):

2.761

ADMET: Toxicity

hERG Blockers:	0.079	hERG Blockers (10um):	0.551
Human Hepatotoxicity (H-HT):	0.622	Drug-induced Liver Injury (DILI):	0.653
AMES Toxicity:	0.819	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.084	Skin Sensitization:	0.997
Carcinogencity:	0.059	Eye Corrosion:	0.0
Eye Irritation:	0.54	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.019	Ototoxicity:	0.837
Hematotoxicity:	0.093	Drug-induced Nephrotoxicity:	0.923
Genotoxicity:	0.405	RPMI-8226 Immunitoxicity:	0.173
A549 Cytotoxicity:	0.249	Hek293 Cytotoxicity:	0.52
BCF:	0.652 ? 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:	4.914 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.136 ? 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
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19435339]
NPO12128	Ipomoea purpurea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12128	Ipomoea purpurea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12128	Ipomoea purpurea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12128	Ipomoea purpurea	Species	Convolvulaceae	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 NPC309320 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	14704
0.1-0.2	29986
0.2-0.3	4180
0.3-0.4	748
0.4-0.5	196
0.5-0.6	35
0.6-0.7	4
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
0.6667	Remote Similarity	NPC288416
0.6471	Remote Similarity	NPC470881
0.6163	Remote Similarity	NPC34293
0.6136	Remote Similarity	NPC252833
0.5823	Remote Similarity	NPC213552
0.5806	Remote Similarity	NPC226005
0.5773	Remote Similarity	NPC300262
0.5747	Remote Similarity	NPC287597
0.57	Remote Similarity	NPC600370
0.566	Remote Similarity	NPC470934
0.566	Remote Similarity	NPC476398
0.5657	Remote Similarity	NPC125823
0.5657	Remote Similarity	NPC7145
0.5657	Remote Similarity	NPC143480
0.549	Remote Similarity	NPC201148
0.5481	Remote Similarity	NPC476382
0.5474	Remote Similarity	NPC476869
0.5455	Remote Similarity	NPC188393
0.5408	Remote Similarity	NPC83743
0.5368	Remote Similarity	NPC235294
0.5315	Remote Similarity	NPC484988
0.5243	Remote Similarity	NPC472611
0.5242	Remote Similarity	NPC487501
0.5238	Remote Similarity	NPC259347
0.5227	Remote Similarity	NPC90318
0.5196	Remote Similarity	NPC34587
0.5169	Remote Similarity	NPC479473
0.5169	Remote Similarity	NPC275721
0.5169	Remote Similarity	NPC479468
0.5169	Remote Similarity	NPC479474
0.5152	Remote Similarity	NPC476865
0.5146	Remote Similarity	NPC3460
0.5133	Remote Similarity	NPC476386
0.5116	Remote Similarity	NPC157554
0.5104	Remote Similarity	NPC471405
0.506	Remote Similarity	NPC120225
0.5055	Remote Similarity	NPC473924
0.5048	Remote Similarity	NPC100998
0.5046	Remote Similarity	NPC479771

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC309320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4665
0.1-0.2	4362
0.2-0.3	117
0.3-0.4	5
0.4-0.5	1
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