NPASS Compound

Natural Product: NPC212376

Natural Product ID	NPC212376
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	N-Lignoceroyltryptamine
IUPAC Name	N-[2-(1H-indol-3-yl)ethyl]tetracosanamide
Synonyms	N-Lignoceroyltryptamine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL492171
PubChem CID	10174581
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

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 95 96 0 0 0 0 0 0 0 0999 V2000 -11.6131 2.5097 1.7270 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2545 1.0780 2.0407 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7791 0.4293 0.7579 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3906 -1.0172 0.9459 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2930 -1.2233 1.9401 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0645 -0.4490 1.4385 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9125 -0.6003 2.3747 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6872 0.1419 1.9418 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2417 -0.3866 0.5902 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0014 0.3283 0.1149 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6080 -0.1984 -1.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3195 -1.6508 -1.1580 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8923 -2.2846 -2.4654 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6463 -1.6429 -2.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4903 -1.7523 -2.0236 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7229 -1.1272 -2.6176 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5326 0.3136 -2.9444 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7711 0.9301 -3.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9139 0.8198 -2.5296 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6214 1.5203 -1.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6222 1.3815 -0.2009 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0184 1.7795 -0.3413 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9281 1.0830 -1.2696 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3164 1.6847 -1.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3012 0.9444 -0.8800 N 0 0 0 0 0 0 0 0 0 0 0 0 9.6310 1.4430 -0.7946 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2095 1.5923 0.5680 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2578 0.3058 1.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3967 -0.4939 1.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0409 -1.5872 2.0834 N 0 0 0 0 0 0 0 0 0 0 0 0 9.7414 -1.5156 2.4133 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9146 -2.3614 3.1132 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5933 -2.0354 3.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0824 -0.8747 2.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8803 0.0009 2.1235 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2017 -0.3245 1.9188 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5286 3.0230 -1.4706 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5275 2.7515 2.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7893 2.6419 0.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7927 3.1624 2.0833 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4937 1.0630 2.8202 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1158 0.4955 2.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6752 0.3938 0.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9441 0.9737 0.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0972 -1.3756 -0.0846 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2846 -1.6415 1.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5744 -0.7493 2.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0393 -2.2900 2.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8256 -0.7507 0.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3725 0.6368 1.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2237 -0.1858 3.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6652 -1.6729 2.5789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8601 -0.0775 2.6499 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8879 1.2288 1.9089 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0129 -1.4612 0.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9917 -0.2682 -0.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1523 1.4293 0.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2036 0.0651 0.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7746 0.4045 -1.6627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4716 -0.0185 -1.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5735 -1.8858 -0.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2926 -2.1648 -0.9025 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6969 -2.3666 -3.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6119 -3.3464 -2.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8514 -0.5845 -3.1583 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3779 -2.1658 -3.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3333 -2.8145 -1.7655 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7559 -1.2583 -1.0434 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9380 -1.6716 -3.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6223 -1.2545 -1.9781 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2641 0.4657 -3.7285 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1439 0.8435 -2.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6271 1.9549 -3.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0804 0.3184 -4.4123 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2363 -0.2165 -2.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7129 1.4662 -3.0567 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6322 1.2100 -0.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4515 2.6182 -1.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1641 1.8248 0.7561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6148 0.2519 0.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0565 2.8906 -0.5695 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4885 1.6896 0.6928 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6235 1.0500 -2.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0663 0.0025 -0.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2969 0.7051 -1.3394 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7454 2.4048 -1.3760 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6679 2.3354 1.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2410 1.9879 0.4686 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3863 -0.2691 0.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7148 -2.3711 2.3189 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3617 -3.2812 3.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9528 -2.7175 3.8738 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0335 -0.6017 2.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4765 0.9210 1.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1657 3.5943 -0.9153 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 2 3 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 24 37 1 0 36 28 1 0 36 31 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 2 42 1 0 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 0 5 48 1 0 6 49 1 0 6 50 1 0 7 51 1 0 7 52 1 0 8 53 1 0 8 54 1 0 9 55 1 0 9 56 1 0 10 57 1 0 10 58 1 0 11 59 1 0 11 60 1 0 12 61 1 0 12 62 1 0 13 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 0 17 72 1 0 18 73 1 0 18 74 1 0 19 75 1 0 19 76 1 0 20 77 1 0 20 78 1 0 21 79 1 0 21 80 1 0 22 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 26 85 1 0 26 86 1 0 27 87 1 0 27 88 1 0 29 89 1 0 30 90 1 0 32 91 1 0 33 92 1 0 34 93 1 0 35 94 1 0 37 95 1 0 M END

Standard InCHIKey	LQPINJBBNVSTDE-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C34H58N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-27-34(37)35-29-28-31-30-36-33-26-24-23-25-32(31)33/h23-26,30,36H,2-22,27-29H2,1H3,(H,35,37)
SMILES	CCCCCCCCCCCCCCCCCCCCCCCC(=NCCc1c[nH]c2ccccc12)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	510.45	Volume:	597.108 ? Van der Waals volume.
Dense:	0.855	LogP:	9.646 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.954 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.789 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	11.0
TPSA:	48.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.575	Fsp³:	0.735
MCE-18:	10.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.714	Fluc inhibitor:	0.09 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.053 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.363 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.006	Promiscuous compounds:	0.246

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.068	MDCK Permeability:	-4.901
Pgp-inhibitor:	0.0	Pgp-substrate:	0.175
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):	0.976
20% Bioavailability (F20%):	0.994	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.948
Plasma Protein Binding (PPB):	101.569%	Volume Distribution (VD):	1.988
Fu:	0.347% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.643
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.99
BSEP inhibitor:	0.833

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.106	CYP2C19-substrate:	0.438
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.452	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.407	CYP2C8-inhibitor:	1.0
HLM stability:	0.776 ? 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):

4.642

Half-life (T1/2):

2.193

ADMET: Toxicity

hERG Blockers:	0.718	hERG Blockers (10um):	0.897
Human Hepatotoxicity (H-HT):	0.836	Drug-induced Liver Injury (DILI):	0.312
AMES Toxicity:	0.132	Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.636	Skin Sensitization:	0.999
Carcinogencity:	0.605	Eye Corrosion:	0.008
Eye Irritation:	0.893	Respiratory Toxicity:	0.996
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.402
Hematotoxicity:	0.211	Drug-induced Nephrotoxicity:	0.354
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.012
A549 Cytotoxicity:	0.833	Hek293 Cytotoxicity:	0.16
BCF:	0.54 ? 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:	5.215 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.675 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.49 ? 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
NPO32731	rollinia mucosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10479316]

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
ED50	6

Activity Type	# Activity
Cell line	5
Non-molecular	1

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
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT83	Cell line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT139	Cell line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[10479318]
NPT306	Cell line	PC-3	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[23755850]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[16448174]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[10479316]

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
-	Artemia salina	LC50	>	500.0	ug.mL-1	PMID[7562925]

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 NPC212376 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	34292
0.1-0.2	14042
0.2-0.3	1107
0.3-0.4	293
0.4-0.5	90
0.5-0.6	10
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259644
1.0	High Similarity	NPC70922
1.0	High Similarity	NPC211572
1.0	High Similarity	NPC75540
1.0	High Similarity	NPC469765
1.0	High Similarity	NPC80597
1.0	High Similarity	NPC25008
1.0	High Similarity	NPC73952
0.8475	Intermediate Similarity	NPC469763
0.75	Intermediate Similarity	NPC190296
0.7333	Intermediate Similarity	NPC105818
0.7273	Intermediate Similarity	NPC311276
0.6769	Remote Similarity	NPC24678
0.5968	Remote Similarity	NPC469760
0.5968	Remote Similarity	NPC469786
0.5932	Remote Similarity	NPC471957
0.5254	Remote Similarity	NPC59269
0.5195	Remote Similarity	NPC486585
0.5156	Remote Similarity	NPC279918
0.5143	Remote Similarity	NPC75907
0.5079	Remote Similarity	NPC282231
0.5079	Remote Similarity	NPC267885
0.5068	Remote Similarity	NPC277920

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC212376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3837
0.1-0.2	5086
0.2-0.3	155
0.3-0.4	54
0.4-0.5	17
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