NPASS Compound

Natural Product: NPC483879

Natural Product ID	NPC483879
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZKNFRNMQEHOVJP-HNNLIEBFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44361756
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 75 79 0 0 0 0 0 0 0 0999 V2000 2.2960 0.1643 -5.0846 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2178 -0.1255 -4.0814 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0060 -0.0573 -4.4212 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4869 -0.4692 -2.7816 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4931 -0.7484 -1.8112 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7371 -2.1973 -1.3914 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4743 -2.5583 -0.5649 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3288 -4.0259 -0.2116 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6891 -1.6687 0.6128 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1915 -1.4179 0.6981 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2509 -1.1230 2.1779 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2844 -0.0533 2.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6726 0.6410 1.3869 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1061 -0.4174 0.6762 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2859 -0.7078 1.5989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7410 0.0694 -0.5926 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1496 0.2277 -0.5211 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8382 1.3982 -0.7033 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1516 2.4295 -0.9583 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2971 1.4993 -0.6167 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0889 0.4241 -0.3458 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4739 0.5872 -0.2769 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0783 1.8005 -0.4730 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2693 2.8833 -0.7465 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9025 2.7134 -0.8129 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 1.3077 0.8722 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0084 2.6253 0.7600 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0866 3.2688 1.2782 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1982 3.1895 0.1500 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4221 4.5535 0.0888 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5671 5.0450 -0.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5241 4.2253 -1.0458 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3010 2.8491 -0.9856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1579 2.3807 -0.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5670 -2.4460 2.5753 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2371 -2.2947 4.0552 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.5312 2.4848 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5091 -2.4876 1.7513 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5712 -2.4815 -1.4575 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2545 -0.2020 -4.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0636 -0.4370 -5.9821 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3102 1.2242 -5.3739 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5278 -0.6579 -2.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7411 -2.8789 -2.2673 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6770 -2.3072 -0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2887 -4.5579 -0.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0935 -4.1394 0.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4275 -4.5319 -0.8457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5759 -0.6833 0.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6747 -2.3905 0.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2511 -1.0348 2.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8879 0.7037 3.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5017 -0.3955 3.2900 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0854 1.3607 1.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2307 -0.9147 1.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1486 -1.6187 2.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5327 0.1604 2.2467 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3896 1.1215 -0.8283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6366 -0.5288 -0.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1333 -0.2551 -0.0619 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1421 1.9763 -0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7203 3.8552 -0.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3083 3.5951 -1.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6647 5.2130 0.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7288 6.1138 -0.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4285 4.6028 -1.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0522 2.1737 -1.4146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0007 1.3082 -0.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5303 -3.1910 4.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7488 -1.4385 4.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1329 -2.2391 4.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6058 -4.1148 1.5780 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4428 -4.2646 3.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5852 -3.0769 2.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3905 -3.0218 -2.2536 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 13 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 11 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 7 39 1 6 16 5 1 0 25 20 1 0 34 29 1 0 14 9 1 0 38 9 1 0 1 40 1 0 1 41 1 0 1 42 1 0 5 43 1 6 6 44 1 0 6 45 1 0 8 46 1 0 8 47 1 0 8 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 1 15 55 1 0 15 56 1 0 15 57 1 0 16 58 1 6 21 59 1 0 22 60 1 0 23 61 1 0 24 62 1 0 25 63 1 0 30 64 1 0 31 65 1 0 32 66 1 0 33 67 1 0 34 68 1 0 36 69 1 0 36 70 1 0 36 71 1 0 37 72 1 0 37 73 1 0 37 74 1 0 39 75 1 0 M END

Standard InCHIKey	ZKNFRNMQEHOVJP-HNNLIEBFSA-N
Standard InCHI	InChI=1S/C31H36O8/c1-19(32)36-23-18-29(4,35)31-17-22(28(2,3)39-31)16-24(37-26(33)20-12-8-6-9-13-20)30(31,5)25(23)38-27(34)21-14-10-7-11-15-21/h6-15,22-25,35H,16-18H2,1-5H3/t22?,23-,24-,25-,29-,30+,31?/m0/s1
SMILES	CC(=O)O[C@H]1C[C@@](C)(C23CC(C[C@@H]([C@]2(C)[C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)C(C)(C)O3)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.24	Volume:	548.543 ? Van der Waals volume.
Dense:	0.978	LogP:	3.645 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.463 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.1 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	29.0
TPSA:	108.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.44	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.561	Fsp³:	0.516
MCE-18:	160.851 ? 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:	0.182	Fluc inhibitor:	0.332 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.099 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.187	Promiscuous compounds:	0.145

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.074	MDCK Permeability:	-4.61
Pgp-inhibitor:	0.869	Pgp-substrate:	0.131
PAMPA:	0.623 ? 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):	0.0
20% Bioavailability (F20%):	0.017	30% Bioavailability (F30%):	0.077
50% Bioavailability (F50%):	0.795

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.397	MRP1:	1.0
Plasma Protein Binding (PPB):	89.042%	Volume Distribution (VD):	-0.051
Fu:	11.033% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.969
OATP1B3 inhibitor:	0.705	BCRP inhibitor:	0.066
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.584
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.021
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.911	CYP3A4-substrate:	0.13
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.601 ? 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):

4.592

Half-life (T1/2):

0.634

ADMET: Toxicity

hERG Blockers:	0.115	hERG Blockers (10um):	0.64
Human Hepatotoxicity (H-HT):	0.101	Drug-induced Liver Injury (DILI):	0.597
AMES Toxicity:	0.238	Rat Oral Acute Toxicity:	0.244
Maximum Recommended Daily Dose:	0.487	Skin Sensitization:	0.967
Carcinogencity:	0.569	Eye Corrosion:	0.0
Eye Irritation:	0.326	Respiratory Toxicity:	0.151
Drug-induced Neurotoxicity:	0.662	Ototoxicity:	0.213
Hematotoxicity:	0.015	Drug-induced Nephrotoxicity:	0.239
Genotoxicity:	0.204	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.506	Hek293 Cytotoxicity:	0.515
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:	3.617 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.205 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.576 ? 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
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11741484]
NPO10966	Maytenus chubutensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11741484]
NPO10966	Maytenus chubutensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10966	Maytenus chubutensis	Species	Celastraceae	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	6

Activity Type	# Activity
Others	6

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
NPT2	Others	Unspecified	n.a.	Inhibition	=	13.3	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	94.0	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	4.1	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	89.7	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	5.3	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	82.0	%	PMID[11741484]

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 NPC483879 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	11513
0.1-0.2	35439
0.2-0.3	2203
0.3-0.4	512
0.4-0.5	143
0.5-0.6	38
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
0.7826	Intermediate Similarity	NPC483878
0.7746	Intermediate Similarity	NPC483874
0.6875	Remote Similarity	NPC481066
0.6338	Remote Similarity	NPC473889
0.625	Remote Similarity	NPC86800
0.6	Remote Similarity	NPC36021
0.5915	Remote Similarity	NPC281717
0.5897	Remote Similarity	NPC25768
0.5875	Remote Similarity	NPC483871
0.5844	Remote Similarity	NPC483875
0.5735	Remote Similarity	NPC147561
0.5714	Remote Similarity	NPC483873
0.5658	Remote Similarity	NPC95265
0.5658	Remote Similarity	NPC97667
0.5616	Remote Similarity	NPC472576
0.5541	Remote Similarity	NPC270590
0.5541	Remote Similarity	NPC158663
0.5522	Remote Similarity	NPC481065
0.5479	Remote Similarity	NPC483886
0.5405	Remote Similarity	NPC483883
0.5405	Remote Similarity	NPC151585
0.5366	Remote Similarity	NPC56953
0.5352	Remote Similarity	NPC195647
0.5352	Remote Similarity	NPC200592
0.5352	Remote Similarity	NPC610542
0.5342	Remote Similarity	NPC152440
0.5342	Remote Similarity	NPC481067
0.5342	Remote Similarity	NPC483882
0.5342	Remote Similarity	NPC483888
0.5341	Remote Similarity	NPC483891
0.5333	Remote Similarity	NPC471101
0.5316	Remote Similarity	NPC479042
0.5263	Remote Similarity	NPC471104
0.5256	Remote Similarity	NPC70716
0.5244	Remote Similarity	NPC469349
0.5185	Remote Similarity	NPC276735
0.5139	Remote Similarity	NPC473081
0.5139	Remote Similarity	NPC270498
0.5128	Remote Similarity	NPC11685
0.5128	Remote Similarity	NPC16912
0.5128	Remote Similarity	NPC472570
0.5065	Remote Similarity	NPC473673
0.5063	Remote Similarity	NPC106895
0.5057	Remote Similarity	NPC294512

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3592
0.1-0.2	5356
0.2-0.3	202
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