NPASS Compound

Natural Product: NPC168369

Natural Product ID	NPC168369
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OQLAYVOSMBSWSF-QWRFVLAXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15628002
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

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 81 0 0 0 0 0 0 0 0999 V2000 -3.4046 3.3378 0.6196 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4671 2.3951 -0.1693 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9121 1.0336 0.1590 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2757 0.1867 -0.8052 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7128 -1.1735 -0.3295 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1603 -2.0406 -1.4675 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9391 -0.9130 0.5484 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6102 -1.7526 0.4537 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5963 -1.5096 1.6677 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5531 -2.5945 -0.1517 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4221 -2.8024 0.8458 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2551 -1.4788 1.1475 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0844 -0.4488 0.3497 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6587 0.9101 0.4826 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1394 1.0031 0.2721 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3885 2.2268 -0.5876 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2868 3.1602 0.1978 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0705 2.8839 -0.8394 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0154 1.8858 -0.4574 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0553 2.6655 0.3134 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9600 2.4922 1.7106 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7049 3.5321 2.5900 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5465 4.6948 2.1521 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6132 3.2995 4.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6624 1.3558 -1.5518 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2144 0.6385 -2.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9894 0.3766 -2.6709 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1000 0.1444 -3.7121 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6723 -0.1555 -0.2631 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6599 -0.9627 0.2223 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1784 -0.6241 1.3174 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1345 -2.1695 -0.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6094 -2.6000 -1.6519 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0706 -3.7435 -2.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0725 -4.5146 -1.7217 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6084 -4.0978 -0.5165 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1369 -2.9454 0.0953 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1372 -1.4363 2.3392 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5340 -3.5839 0.2131 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2393 4.3454 0.2019 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0840 3.3041 1.6746 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4223 2.9541 0.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5749 2.6677 -1.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9297 0.7543 1.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2589 0.4611 -1.8368 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1209 -3.0923 -1.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5453 -1.9189 -2.3757 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2219 -1.8046 -1.6948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5470 -0.1471 0.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6156 -0.5206 1.5375 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5007 -1.8454 0.7002 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1678 -2.2583 -1.0892 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9661 -3.6345 -0.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7493 -3.3061 1.7561 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5591 -0.5678 -0.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4481 1.2462 1.5562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6632 1.1557 1.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8833 1.9905 -1.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8805 3.1753 1.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3101 2.7787 0.2753 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2179 4.1866 -0.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9540 3.2073 -1.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9987 3.8166 -0.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8878 3.7541 0.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6023 3.4131 4.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0698 4.0549 4.4941 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2510 2.2692 4.2818 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7238 -0.6607 -3.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7506 1.0020 -3.9990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4991 -0.1590 -4.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8146 -1.9853 -2.0820 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6490 -4.0631 -3.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4432 -5.4175 -2.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3878 -4.6803 -0.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5617 -2.6303 1.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4939 -0.4341 2.5782 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5577 -1.7996 3.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9985 -2.1545 2.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1243 -4.1327 -0.4771 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 1 0 5 7 1 0 5 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 19 25 1 6 25 26 1 0 26 27 2 0 26 28 1 0 15 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 12 38 1 0 11 39 1 0 20 2 1 0 37 32 1 0 19 14 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 6 3 44 1 0 4 45 1 0 6 46 1 0 6 47 1 0 6 48 1 0 7 49 1 0 7 50 1 0 7 51 1 0 10 52 1 0 10 53 1 0 11 54 1 1 13 55 1 0 14 56 1 1 15 57 1 1 16 58 1 6 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 20 64 1 1 24 65 1 0 24 66 1 0 24 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 33 71 1 0 34 72 1 0 35 73 1 0 36 74 1 0 37 75 1 0 38 76 1 0 38 77 1 0 38 78 1 0 39 79 1 0 M END

Standard InCHIKey	OQLAYVOSMBSWSF-QWRFVLAXSA-N
Standard InCHI	InChI=1S/C31H40O8/c1-18-13-14-30(6,7)26(35)16-25(34)19(2)15-24-27(38-29(36)23-11-9-8-10-12-23)20(3)17-31(24,39-22(5)33)28(18)37-21(4)32/h8-15,18,20,24-25,27-28,34H,16-17H2,1-7H3/b14-13+,19-15+/t18-,20-,24+,25-,27+,28-,31-/m1/s1
SMILES	C[C@@H]1/C=C/C(C)(C)C(=O)C[C@H](/C(=C/[C@H]2[C@H]([C@H](C)C[C@@]2([C@@H]1OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)/C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	540.27	Volume:	565.656 ? Van der Waals volume.
Dense:	0.955	LogP:	2.394 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.64 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.013 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	26.0
TPSA:	116.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.335	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.254	Fsp³:	0.548
MCE-18:	92.25 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.929	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.021 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.196	Promiscuous compounds:	0.281

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.325	MDCK Permeability:	-4.929
Pgp-inhibitor:	1.0	Pgp-substrate:	0.126
PAMPA:	0.181 ? 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):	0.002
20% Bioavailability (F20%):	0.924	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.997
Plasma Protein Binding (PPB):	91.758%	Volume Distribution (VD):	-0.132
Fu:	7.858% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.215
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.013
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.058	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.999 ? 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):

8.113

Half-life (T1/2):

0.428

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.191
Human Hepatotoxicity (H-HT):	0.572	Drug-induced Liver Injury (DILI):	0.933
AMES Toxicity:	0.233	Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.445	Skin Sensitization:	0.962
Carcinogencity:	0.36	Eye Corrosion:	0.001
Eye Irritation:	0.359	Respiratory Toxicity:	0.081
Drug-induced Neurotoxicity:	0.652	Ototoxicity:	0.499
Hematotoxicity:	0.189	Drug-induced Nephrotoxicity:	0.871
Genotoxicity:	0.935	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.272	Hek293 Cytotoxicity:	0.401
BCF:	0.623 ? 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:	3.393 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.951 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.426 ? 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
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18321057]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19099222]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724086]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550154]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	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	4
Activity	2

Activity Type	# Activity
Individual protein	4
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2854	Individual protein	Voltage-gated potassium channel subunit Kv1.3	Homo sapiens	Inhibition	=	94.56	%	PMID[35245067]
NPT2854	Individual protein	Voltage-gated potassium channel subunit Kv1.3	Homo sapiens	Inhibition	=	2.38	%	PMID[35245067]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell line	HEK293	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35245067]

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 NPC168369 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	7919
0.1-0.2	37461
0.2-0.3	3815
0.3-0.4	571
0.4-0.5	65
0.5-0.6	12
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209778
0.7534	Intermediate Similarity	NPC600912
0.75	Intermediate Similarity	NPC153617
0.7432	Intermediate Similarity	NPC600781
0.7432	Intermediate Similarity	NPC611288
0.7333	Intermediate Similarity	NPC242355
0.6753	Remote Similarity	NPC472248
0.6494	Remote Similarity	NPC604501
0.6429	Remote Similarity	NPC608808
0.6364	Remote Similarity	NPC602572
0.6203	Remote Similarity	NPC482360
0.6125	Remote Similarity	NPC600127
0.6125	Remote Similarity	NPC611555
0.6	Remote Similarity	NPC472250
0.5926	Remote Similarity	NPC604953
0.5926	Remote Similarity	NPC605971
0.5844	Remote Similarity	NPC604476
0.5625	Remote Similarity	NPC482320
0.561	Remote Similarity	NPC610855
0.5595	Remote Similarity	NPC605737
0.5476	Remote Similarity	NPC601126
0.5476	Remote Similarity	NPC609000
0.5349	Remote Similarity	NPC200154
0.5244	Remote Similarity	NPC196683
0.5116	Remote Similarity	NPC604735
0.5059	Remote Similarity	NPC311492

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC168369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3473
0.1-0.2	5463
0.2-0.3	211
0.3-0.4	3
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