NPASS Compound

Natural Product: NPC79012

Natural Product ID	NPC79012
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GTHKEJRKRGQZPU-PCNNKYCXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11786042
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

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 70 73 0 0 0 0 0 0 0 0999 V2000 -2.2169 4.0187 -2.4507 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4357 3.0984 -1.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1429 2.9659 -2.2751 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8389 2.2567 -1.8722 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8798 1.3457 -0.7080 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8532 -0.1153 -0.9951 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4869 -0.3340 -2.4283 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2478 -0.6918 -0.9097 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2599 -2.1044 -1.5621 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0214 -2.8737 -1.3006 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2518 -2.3953 -0.1297 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4661 -3.2525 1.1340 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6660 -3.2729 0.3917 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1118 -0.9155 0.0438 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1303 -0.4107 0.6523 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3465 -0.1214 -0.0928 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9908 -1.2765 -0.8119 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8715 -2.1227 0.0400 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9006 -0.5705 -1.7535 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5848 -1.1856 -2.6540 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8486 0.7706 -1.4661 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4262 0.9486 -1.0942 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1812 2.3712 -0.7476 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9501 2.7941 0.9193 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.3253 0.2714 0.8678 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3866 -1.0586 1.9279 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2856 -0.5687 3.1571 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9191 0.6154 3.2387 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5639 -1.2867 4.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7543 -0.8303 0.3942 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9974 -0.3887 0.7391 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7737 0.1660 -0.0876 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5505 -0.5212 2.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1801 1.7511 -0.1344 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2956 2.4117 1.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2686 2.6964 1.7109 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5959 2.8301 1.6389 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8551 4.5719 -3.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2248 4.1632 -2.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0801 3.5928 -3.1976 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7728 2.3551 -2.5042 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2406 1.6789 0.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4123 -0.9128 -2.6256 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2478 0.6571 -2.9392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2849 -0.7026 -3.0960 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9386 -0.0738 -1.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6030 -2.0627 -2.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1458 -2.5962 -1.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3963 -3.0688 -2.2052 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3774 -3.9382 -1.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1050 -4.1484 1.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6289 -2.6550 2.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 -0.7609 0.9297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8512 0.5559 1.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2358 -1.8766 -1.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6487 -2.6288 -0.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4824 -1.4186 0.6779 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3713 -2.8720 0.6499 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9680 0.7878 -2.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2949 2.8256 -0.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0956 0.6788 0.4397 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1915 -0.6426 5.1021 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0509 -2.2538 4.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5820 -1.4615 4.9184 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2804 -1.3753 2.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7798 -0.7651 2.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1427 0.3752 2.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4459 2.6941 0.9566 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5049 3.9244 1.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7813 2.3378 2.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 16 25 1 1 15 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 8 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 5 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 23 2 1 0 14 6 1 0 22 16 1 0 11 13 1 6 1 38 1 0 1 39 1 0 3 40 1 0 4 41 1 0 5 42 1 1 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 6 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 12 52 1 0 14 53 1 1 15 54 1 1 17 55 1 6 18 56 1 0 18 57 1 0 18 58 1 0 22 59 1 6 23 60 1 6 25 61 1 0 29 62 1 0 29 63 1 0 29 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 37 68 1 0 37 69 1 0 37 70 1 0 M END

Standard InCHIKey	GTHKEJRKRGQZPU-PCNNKYCXSA-N
Standard InCHI	InChI=1S/C26H33ClO10/c1-12-7-8-17(34-14(3)28)24(6)18(35-15(4)29)9-10-25(11-33-25)20(24)22(36-16(5)30)26(32)13(2)23(31)37-21(26)19(12)27/h7-8,13,17-22,32H,1,9-11H2,2-6H3/b8-7-/t13-,17-,18-,19-,20+,21-,22-,24-,25+,26-/m0/s1
SMILES	C=C1/C=C[C@@H]([C@@]2(C)[C@H](CC[C@@]3(CO3)[C@@H]2[C@@H]([C@@]2([C@@H](C)C(=O)O[C@H]2[C@H]1Cl)O)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	540.18	Volume:	511.321 ? Van der Waals volume.
Dense:	1.056	LogP:	2.045 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.207 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.624 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	27.0
TPSA:	137.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.245	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.196	Fsp³:	0.692
MCE-18:	118.5 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.486	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.386	Promiscuous compounds:	0.556

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.006	MDCK Permeability:	-4.675
Pgp-inhibitor:	0.994	Pgp-substrate:	0.313
PAMPA:	0.928 ? 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):	0.001
20% Bioavailability (F20%):	0.08	30% Bioavailability (F30%):	0.851
50% Bioavailability (F50%):	0.766

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.968
Plasma Protein Binding (PPB):	52.527%	Volume Distribution (VD):	-0.296
Fu:	47.385% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.961	BCRP inhibitor:	0.004
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.917	CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.214	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.281
CYP2D6-inhibitor:	0.025	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.528
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.994 ? 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):

4.371

Half-life (T1/2):

1.255

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.026
Human Hepatotoxicity (H-HT):	0.821	Drug-induced Liver Injury (DILI):	0.96
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.658	Skin Sensitization:	1.0
Carcinogencity:	0.745	Eye Corrosion:	0.16
Eye Irritation:	0.361	Respiratory Toxicity:	0.706
Drug-induced Neurotoxicity:	0.196	Ototoxicity:	0.36
Hematotoxicity:	0.77	Drug-induced Nephrotoxicity:	0.97
Genotoxicity:	0.988	RPMI-8226 Immunitoxicity:	0.298
A549 Cytotoxicity:	0.614	Hek293 Cytotoxicity:	0.131
BCF:	0.595 ? 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:	3.313 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.917 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.538 ? 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
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	n.a.	stem	n.a.	PMID[18310955]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547115]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5217	Allium macleanii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5217	Allium macleanii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2456	Sedum maximum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10162	Cyclea burmanni	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	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 NPC79012 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	17244
0.1-0.2	30445
0.2-0.3	2104
0.3-0.4	12
0.4-0.5	17
0.5-0.6	13
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC602049
0.9516	High Similarity	NPC606141
0.8939	High Similarity	NPC600027
0.8551	High Similarity	NPC483347
0.7536	Intermediate Similarity	NPC310035
0.7536	Intermediate Similarity	NPC601003
0.7391	Intermediate Similarity	NPC483349
0.7246	Intermediate Similarity	NPC608960
0.7222	Intermediate Similarity	NPC282003
0.7059	Intermediate Similarity	NPC609324
0.7042	Intermediate Similarity	NPC600649
0.6857	Remote Similarity	NPC128210
0.6857	Remote Similarity	NPC605077
0.6667	Remote Similarity	NPC605719
0.6667	Remote Similarity	NPC606671
0.6622	Remote Similarity	NPC606973
0.6575	Remote Similarity	NPC188222
0.6575	Remote Similarity	NPC610469
0.6364	Remote Similarity	NPC303006
0.6364	Remote Similarity	NPC483351
0.6104	Remote Similarity	NPC606818
0.6076	Remote Similarity	NPC606893
0.6027	Remote Similarity	NPC483348
0.5904	Remote Similarity	NPC470185
0.5875	Remote Similarity	NPC605084
0.5556	Remote Similarity	NPC483344
0.5556	Remote Similarity	NPC94377
0.5526	Remote Similarity	NPC154799
0.5333	Remote Similarity	NPC3287
0.5316	Remote Similarity	NPC156248
0.5316	Remote Similarity	NPC140409
0.5278	Remote Similarity	NPC483342
0.5205	Remote Similarity	NPC483343
0.5195	Remote Similarity	NPC89018
0.5185	Remote Similarity	NPC11491
0.506	Remote Similarity	NPC170294

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC79012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6368
0.1-0.2	2759
0.2-0.3	23
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