NPASS Compound

Natural Product: NPC240470

Natural Product ID	NPC240470
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Methyl Pentacosanoate
IUPAC Name	methyl pentacosanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	41431
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters [CHEMONTID:0003417] Fatty acid methyl esters

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 79 0 0 0 0 0 0 0 0999 V2000 -10.2193 -1.0230 1.6506 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0197 -1.9570 1.5432 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8292 -1.3269 2.2695 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4894 0.0103 1.6361 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3163 0.6491 2.3421 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0842 -0.1897 2.2871 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6132 -0.4673 0.8825 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3096 0.8285 0.2008 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8294 0.6871 -1.2108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5790 -0.1026 -1.3561 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4330 0.5028 -0.5870 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1794 1.8968 -1.1083 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0339 2.5734 -0.3930 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2112 1.7754 -0.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5422 1.6673 -2.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8374 0.8355 -2.1236 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2206 0.6932 -3.5511 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4738 -0.0664 -3.7695 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6037 -1.4574 -3.3843 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5308 -2.0492 -2.0669 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5025 -1.7100 -0.9965 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5620 -0.3355 -0.4921 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6319 -0.1742 0.6037 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3724 -1.0566 1.7867 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4641 -0.8060 2.7619 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4061 0.2300 3.4704 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5521 -1.6467 2.9437 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5885 -1.4180 3.8630 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1366 -1.6458 1.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1018 -0.2392 0.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2492 -0.5597 2.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7800 -2.0523 0.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2400 -2.9518 1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0800 -1.2052 3.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0034 -2.0518 2.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3672 0.6705 1.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2004 -0.1830 0.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6164 0.6965 3.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1626 1.6955 2.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2693 0.3721 2.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2837 -1.1552 2.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6337 -1.0162 0.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3613 -1.0487 0.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6126 1.4062 0.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2526 1.4484 0.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7348 1.6968 -1.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6428 0.2020 -1.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7047 -1.1842 -1.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2645 -0.0630 -2.4411 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6802 0.5994 0.4934 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5196 -0.1289 -0.6869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0686 2.5563 -0.9588 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0123 1.8648 -2.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2638 2.6339 0.6932 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0881 3.5651 -0.8224 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0394 2.3397 -0.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1900 0.7822 -0.1009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8047 1.1065 -2.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7424 2.6512 -2.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6083 1.5020 -1.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7362 -0.0710 -1.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3657 0.2867 -4.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4236 1.7567 -3.9166 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6435 -0.0263 -4.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3125 0.6090 -3.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8401 -2.0741 -4.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5765 -1.8995 -3.8775 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4766 -2.1529 -1.6598 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7177 -3.2103 -2.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3956 -2.4778 -0.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5285 -2.0010 -1.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8613 0.3783 -1.2598 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5801 -0.0238 -0.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6014 -0.3778 0.1525 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5650 0.8716 0.9377 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4132 -2.1411 1.5539 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4100 -0.8718 2.2738 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3134 -0.6650 3.4426 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1804 -2.3714 3.9107 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2639 -1.0650 4.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 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 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 1 29 1 0 1 30 1 0 1 31 1 0 2 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 0 18 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 21 70 1 0 21 71 1 0 22 72 1 0 22 73 1 0 23 74 1 0 23 75 1 0 24 76 1 0 24 77 1 0 28 78 1 0 28 79 1 0 28 80 1 0 M END

Standard InCHIKey	WOPKHAQDUMDJIY-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C26H52O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26(27)28-2/h3-25H2,1-2H3
SMILES	CCCCCCCCCCCCCCCCCCCCCCCCC(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	396.4	Volume:	473.196 ? Van der Waals volume.
Dense:	0.838	LogP:	9.407 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.898 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.863 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	1.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.127	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.764	Fsp³:	0.962
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.582	Fluc inhibitor:	0.28 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.994	Promiscuous compounds:	0.297

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.055	MDCK Permeability:	-4.926
Pgp-inhibitor:	0.001	Pgp-substrate:	0.034
PAMPA:	0.0 ? 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):	0.949
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.999
Plasma Protein Binding (PPB):	101.267%	Volume Distribution (VD):	1.782
Fu:	0.47% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.118
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.986
BSEP inhibitor:	0.96

ADMET: Metabolism

CYP1A2-inhibitor:	0.017	CYP1A2-substrate:	0.995
CYP2C19-inhibitor:	0.062	CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.976	CYP2C9-substrate:	0.306
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.887	CYP2C8-inhibitor:	1.0
HLM stability:	0.79 ? 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):

4.663

Half-life (T1/2):

2.209

ADMET: Toxicity

hERG Blockers:	0.679	hERG Blockers (10um):	0.914
Human Hepatotoxicity (H-HT):	0.46	Drug-induced Liver Injury (DILI):	0.113
AMES Toxicity:	0.024	Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.283	Skin Sensitization:	0.996
Carcinogencity:	0.347	Eye Corrosion:	0.99
Eye Irritation:	0.996	Respiratory Toxicity:	0.975
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.144
Hematotoxicity:	0.151	Drug-induced Nephrotoxicity:	0.22
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.687	Hek293 Cytotoxicity:	0.077
BCF:	0.403 ? 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:	4.955 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.523 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.885 ? 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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	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
NPO12006	Apis mellifera	n.a.	n.a.	0.001	n.a.	n.a.	%	PMID[24926420]

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 NPC240470 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	23936
0.1-0.2	23582
0.2-0.3	1971
0.3-0.4	265
0.4-0.5	53
0.5-0.6	21
0.6-0.7	17
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201622
1.0	High Similarity	NPC305660
1.0	High Similarity	NPC161097
1.0	High Similarity	NPC28598
1.0	High Similarity	NPC22903
1.0	High Similarity	NPC54980
0.8333	Intermediate Similarity	NPC219536
0.8333	Intermediate Similarity	NPC31551
0.7895	Intermediate Similarity	NPC476548
0.7778	Intermediate Similarity	NPC57499
0.75	Intermediate Similarity	NPC309606
0.7222	Intermediate Similarity	NPC28246
0.7143	Intermediate Similarity	NPC12156
0.6923	Remote Similarity	NPC106872
0.6923	Remote Similarity	NPC228473
0.6842	Remote Similarity	NPC602319
0.6667	Remote Similarity	NPC39633
0.6522	Remote Similarity	NPC47363
0.6522	Remote Similarity	NPC250028
0.6522	Remote Similarity	NPC236579
0.6522	Remote Similarity	NPC80234
0.6522	Remote Similarity	NPC287231
0.6522	Remote Similarity	NPC203531
0.6522	Remote Similarity	NPC256163
0.6522	Remote Similarity	NPC40597
0.6522	Remote Similarity	NPC317128
0.625	Remote Similarity	NPC216130
0.6	Remote Similarity	NPC12438
0.6	Remote Similarity	NPC30195
0.6	Remote Similarity	NPC603863
0.5769	Remote Similarity	NPC603612
0.5652	Remote Similarity	NPC53541
0.5556	Remote Similarity	NPC149299
0.5556	Remote Similarity	NPC310746
0.5517	Remote Similarity	NPC139545
0.5357	Remote Similarity	NPC26253
0.5357	Remote Similarity	NPC23155
0.5263	Remote Similarity	NPC8187
0.52	Remote Similarity	NPC326957
0.52	Remote Similarity	NPC63182
0.52	Remote Similarity	NPC145045
0.52	Remote Similarity	NPC52700
0.5185	Remote Similarity	NPC80396
0.5185	Remote Similarity	NPC154642
0.5185	Remote Similarity	NPC600941
0.5172	Remote Similarity	NPC488257
0.5172	Remote Similarity	NPC469937
0.5172	Remote Similarity	NPC94699
0.5172	Remote Similarity	NPC128061
0.5172	Remote Similarity	NPC320588
0.5172	Remote Similarity	NPC53463

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC240470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6798
0.1-0.2	2182
0.2-0.3	146
0.3-0.4	19
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6522	Remote Similarity	NPD2699	Pre-clinical

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