NPASS Compound

Natural Product: NPC469349

Natural Product ID	NPC469349
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RPIUOWOTQONAKE-GVZSNRDBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1076617
PubChem CID	46880538
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 80 84 0 0 0 0 0 0 0 0999 V2000 -6.8644 -1.9951 1.2128 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3854 -1.8244 1.3087 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8268 -1.8041 2.4296 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6130 -1.6879 0.1921 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2212 -1.5262 0.2366 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7269 -0.2627 -0.3707 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2656 -0.1200 0.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4021 -1.1958 -0.4568 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9458 -1.1338 0.2277 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5611 -2.4678 0.5087 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6571 -3.5637 0.9329 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7135 -2.9249 1.2047 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0160 -2.5428 -0.2537 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4782 -2.6668 -0.4238 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9207 -2.9113 -1.8404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8804 -3.8227 0.2941 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3964 -3.4889 -1.0511 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2656 -4.4017 -0.2943 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 -4.9062 -0.9543 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5169 -5.6226 0.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8313 -0.4291 -0.6411 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5232 0.7327 -0.2163 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2958 1.0608 0.9369 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4006 1.4140 -1.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1607 2.4284 -1.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5742 3.4740 -0.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1652 3.6328 1.0546 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6119 4.6824 1.8671 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4950 5.6165 1.3938 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9222 5.4811 0.0948 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4821 4.4560 -0.6891 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2440 -0.8979 -1.9558 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9042 1.1955 -0.2449 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6951 2.2201 0.6592 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8375 1.9603 1.8809 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3218 3.5751 0.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1471 3.9341 -1.0358 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2100 5.2374 -1.3731 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3926 6.1781 -0.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2266 5.8539 0.9120 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1290 4.5521 1.2338 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4391 0.8148 0.1336 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3265 -1.0022 1.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1948 -2.7207 1.9974 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0703 -2.3831 0.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9198 -1.5349 1.3055 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7450 -0.2137 -1.4587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3423 -0.2279 1.2066 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9349 -0.5674 1.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1574 -2.8466 -0.3727 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3120 -2.3412 1.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9968 -4.1749 1.7659 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4338 -3.6404 1.5931 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5275 -2.0496 1.8224 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0478 -2.0139 -2.4423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8572 -3.5054 -1.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1588 -3.5487 -2.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8614 -3.7288 0.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8599 -4.2808 -1.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4126 -5.9432 -1.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3584 -4.9799 -0.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3115 -5.8736 -0.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1360 -6.5452 0.1198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9266 -5.5622 1.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4362 0.8811 -2.1747 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6790 2.5580 -2.1618 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4877 2.9823 1.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2725 4.7883 2.8968 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8231 6.4132 2.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6297 6.2246 -0.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8650 4.4185 -1.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8532 -0.8933 -2.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5917 0.1259 -2.2007 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6797 -1.6844 -2.5845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2795 3.2265 -1.8423 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3525 5.5402 -2.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6747 7.2152 -0.6327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3747 6.6127 1.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2495 4.3410 2.2892 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4209 0.6307 0.1248 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 8 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 0 14 16 1 0 13 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 9 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 3 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 8 32 1 0 7 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 6 42 1 0 14 5 1 0 13 8 1 0 18 11 1 0 31 26 1 0 41 36 1 0 1 43 1 0 1 44 1 0 1 45 1 0 5 46 1 0 6 47 1 0 7 48 1 0 9 49 1 0 10 50 1 0 10 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 15 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 20 64 1 0 24 65 1 0 25 66 1 0 27 67 1 0 28 68 1 0 29 69 1 0 30 70 1 0 31 71 1 0 32 72 1 0 32 73 1 0 32 74 1 0 37 75 1 0 38 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 M END

Standard InCHIKey	RPIUOWOTQONAKE-GVZSNRDBSA-N
Standard InCHI	InChI=1S/C33H38O9/c1-20(34)39-28-26(36)27(41-29(37)22-14-10-7-11-15-22)31(4)24(40-25(35)17-16-21-12-8-6-9-13-21)18-23-19-33(31,32(28,5)38)42-30(23,2)3/h6-17,23-24,26-28,36,38H,18-19H2,1-5H3/b17-16+/t23-,24+,26+,27+,28+,31-,32+,33-/m1/s1
SMILES	CC(=O)OC1C(C(C2(C(CC3CC2(C1(C)O)OC3(C)C)OC(=O)C=CC4=CC=CC=C4)C)OC(=O)C5=CC=CC=C5)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.25	Volume:	589.289 ? Van der Waals volume.
Dense:	0.981	LogP:	3.976 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.497 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.93 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	128.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.298	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.832	Fsp³:	0.485
MCE-18:	164.612 ? 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:	0.897	Fluc inhibitor:	0.334 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.037 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.657 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.018

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.483	MDCK Permeability:	-4.969
Pgp-inhibitor:	0.131	Pgp-substrate:	0.217
PAMPA:	0.931 ? 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):	0.003
20% Bioavailability (F20%):	0.022	30% Bioavailability (F30%):	0.517
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156	MRP1:	1.0
Plasma Protein Binding (PPB):	89.815%	Volume Distribution (VD):	-0.041
Fu:	9.32% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.049
OATP1B3 inhibitor:	0.736	BCRP inhibitor:	0.002
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.029	CYP3A4-substrate:	0.785
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.101 ? 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):

1.554

Half-life (T1/2):

1.506

ADMET: Toxicity

hERG Blockers:	0.125	hERG Blockers (10um):	0.727
Human Hepatotoxicity (H-HT):	0.126	Drug-induced Liver Injury (DILI):	0.356
AMES Toxicity:	0.285	Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.438	Skin Sensitization:	0.984
Carcinogencity:	0.17	Eye Corrosion:	0.0
Eye Irritation:	0.07	Respiratory Toxicity:	0.046
Drug-induced Neurotoxicity:	0.652	Ototoxicity:	0.778
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.222
Genotoxicity:	0.028	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.151	Hek293 Cytotoxicity:	0.784
BCF:	1.1 ? 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:	4.065 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.567 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.133 ? 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
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26437	Maytenus jelskii	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
Activity	5

Activity Type	# Activity
Cell line	1
Others	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[8411013]
NPT2	Others	Unspecified	n.a.	Activity	=	10.9	%	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified	n.a.	Activity	=	52.0	%	PMID[23964644]
NPT2	Others	Unspecified	n.a.	Activity	=	86.2	%	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PubChem BioAssay data set

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 NPC469349 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	9786
0.1-0.2	36073
0.2-0.3	3268
0.3-0.4	629
0.4-0.5	69
0.5-0.6	26
0.6-0.7	3
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
0.7564	Intermediate Similarity	NPC25768
0.7	Intermediate Similarity	NPC483878
0.6264	Remote Similarity	NPC483891
0.6098	Remote Similarity	NPC214550
0.6047	Remote Similarity	NPC483861
0.5795	Remote Similarity	NPC188865
0.5795	Remote Similarity	NPC171525
0.5714	Remote Similarity	NPC86800
0.5682	Remote Similarity	NPC174982
0.5618	Remote Similarity	NPC184817
0.5506	Remote Similarity	NPC483865
0.5455	Remote Similarity	NPC483867
0.5435	Remote Similarity	NPC470245
0.5426	Remote Similarity	NPC483873
0.5393	Remote Similarity	NPC483866
0.5393	Remote Similarity	NPC473109
0.5309	Remote Similarity	NPC84129
0.5301	Remote Similarity	NPC475933
0.5281	Remote Similarity	NPC472571
0.5275	Remote Similarity	NPC483859
0.5253	Remote Similarity	NPC483880
0.5253	Remote Similarity	NPC156941
0.5244	Remote Similarity	NPC37641
0.5244	Remote Similarity	NPC114927
0.5244	Remote Similarity	NPC483879
0.5222	Remote Similarity	NPC70403
0.5222	Remote Similarity	NPC177940
0.5222	Remote Similarity	NPC605086
0.5165	Remote Similarity	NPC483860
0.5114	Remote Similarity	NPC473085
0.5111	Remote Similarity	NPC470159

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469349 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3942
0.1-0.2	5076
0.2-0.3	129
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