NPASS Compound

Natural Product: NPC483883

Natural Product ID	NPC483883
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SOTGPCCKMHIJCT-PDHFZSAVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44361783
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 81 85 0 0 0 0 0 0 0 0999 V2000 1.6703 3.1582 0.8287 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7684 1.9771 1.0006 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6743 0.8116 1.4235 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7699 -0.4026 1.4213 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6036 -0.7551 -0.0434 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1620 0.3862 -0.8800 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1914 0.6510 -1.9609 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1109 -0.0029 -1.5894 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7917 1.1421 -2.2696 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8085 2.4081 -1.5116 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3376 2.7157 -1.1433 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1543 1.6643 -0.1019 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4348 1.3996 0.4470 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3340 2.2663 -0.0950 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3293 3.6141 0.5985 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7449 1.7897 -0.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2883 4.0348 -0.7347 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3614 4.9838 -1.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9220 4.6658 -2.5486 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3944 6.3848 -1.0138 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9239 -0.6991 -0.6974 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2976 -2.0183 -0.8389 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8798 -2.6398 -1.8404 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1537 -2.6227 0.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5789 -1.8956 1.2606 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3894 -2.4456 2.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7969 -3.7505 2.1320 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3909 -4.5047 1.0609 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5704 -3.9425 0.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8997 -1.2144 -0.4642 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1786 -2.5077 -0.7980 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2394 -3.3626 -0.7338 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5149 -2.8710 -1.2106 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5129 -1.9377 -1.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8066 -2.2718 -1.6727 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0825 -3.5760 -2.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0859 -4.5528 -1.9509 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8007 -4.1715 -1.5466 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2743 -1.4819 2.1406 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6559 -2.0248 3.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4345 -1.4994 3.6199 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1800 -3.1716 4.0232 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1430 1.0923 2.6917 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1318 4.0796 1.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4919 3.0689 1.6040 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1928 3.2209 -0.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1886 2.1890 1.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4701 0.7590 0.6803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1875 -0.0787 1.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0296 -1.6594 -0.0679 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7120 0.7928 -2.9717 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8371 -0.2586 -2.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8887 1.4661 -1.7254 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8196 -0.7426 -2.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2351 1.3386 -3.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7940 0.8049 -2.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2575 3.2127 -2.0700 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2071 2.5504 -2.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4613 3.7730 1.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5003 4.4554 -0.1146 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2179 3.6632 1.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9579 1.1197 -0.9694 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4655 2.6515 -0.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0723 1.3407 0.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3516 6.5283 -0.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4149 6.5797 -0.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3318 7.1263 -1.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2791 -0.8550 1.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7331 -1.8797 3.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4244 -4.1679 2.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6764 -5.5364 0.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2306 -4.5135 -0.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3058 -0.8975 -1.0127 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5969 -1.5479 -1.7276 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0909 -3.8142 -2.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3240 -5.5639 -2.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0662 -4.9779 -1.5225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5562 -2.7903 5.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0470 -3.5919 3.4878 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4149 -3.9605 4.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4101 1.2927 3.3073 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 6 6 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 11 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 8 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 5 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 4 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 3 43 1 0 12 2 1 0 29 24 1 0 38 33 1 0 12 6 1 0 14 10 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 1 3 48 1 6 4 49 1 1 5 50 1 1 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 6 9 55 1 0 9 56 1 0 10 57 1 0 11 58 1 6 15 59 1 0 15 60 1 0 15 61 1 0 16 62 1 0 16 63 1 0 16 64 1 0 20 65 1 0 20 66 1 0 20 67 1 0 25 68 1 0 26 69 1 0 27 70 1 0 28 71 1 0 29 72 1 0 34 73 1 0 35 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 42 78 1 0 42 79 1 0 42 80 1 0 43 81 1 0 M END

Standard InCHIKey	SOTGPCCKMHIJCT-PDHFZSAVSA-N
Standard InCHI	InChI=1S/C33H38O10/c1-18-25(36)26(39-19(2)34)28(42-30(38)22-15-11-8-12-16-22)32(6)24(41-29(37)21-13-9-7-10-14-21)17-23-27(40-20(3)35)33(18,32)43-31(23,4)5/h7-16,18,23-28,36H,17H2,1-6H3/t18-,23?,24+,25-,26+,27-,28+,32-,33?/m1/s1
SMILES	C[C@@H]1[C@H]([C@@H]([C@@H]([C@@]2(C)[C@H](CC3[C@H](C12OC3(C)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.25	Volume:	598.079 ? Van der Waals volume.
Dense:	0.994	LogP:	3.044 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.095 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.531 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	134.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.388	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.752	Fsp³:	0.515
MCE-18:	164.28 ? 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:	0.831	Fluc inhibitor:	0.014 ? 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:	0.061 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.12	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.203	MDCK Permeability:	-4.794
Pgp-inhibitor:	0.999	Pgp-substrate:	0.414
PAMPA:	0.541 ? 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%):	0.029	30% Bioavailability (F30%):	0.158
50% Bioavailability (F50%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167	MRP1:	1.0
Plasma Protein Binding (PPB):	73.342%	Volume Distribution (VD):	-0.187
Fu:	21.976% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.923	BCRP inhibitor:	0.115
BSEP inhibitor:	0.983

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.199	CYP3A4-substrate:	0.02
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.723 ? 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):

4.697

Half-life (T1/2):

0.594

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.59
Human Hepatotoxicity (H-HT):	0.118	Drug-induced Liver Injury (DILI):	0.894
AMES Toxicity:	0.312	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.162	Skin Sensitization:	0.985
Carcinogencity:	0.476	Eye Corrosion:	0.001
Eye Irritation:	0.29	Respiratory Toxicity:	0.034
Drug-induced Neurotoxicity:	0.496	Ototoxicity:	0.22
Hematotoxicity:	0.043	Drug-induced Nephrotoxicity:	0.292
Genotoxicity:	0.447	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.413	Hek293 Cytotoxicity:	0.345
BCF:	0.747 ? 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:	3.66 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.424 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.878 ? 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	=	11.7	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	77.5	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	3.5	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	54.0	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	0.0	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	32.0	%	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 NPC483883 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	11694
0.1-0.2	35416
0.2-0.3	2153
0.3-0.4	403
0.4-0.5	123
0.5-0.6	53
0.6-0.7	9
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	NPC151585
0.7887	Intermediate Similarity	NPC483865
0.7015	Intermediate Similarity	NPC483862
0.6957	Remote Similarity	NPC158663
0.6818	Remote Similarity	NPC473081
0.6818	Remote Similarity	NPC195647
0.6714	Remote Similarity	NPC270590
0.6418	Remote Similarity	NPC474608
0.6324	Remote Similarity	NPC200592
0.6324	Remote Similarity	NPC270498
0.6324	Remote Similarity	NPC610542
0.6027	Remote Similarity	NPC27377
0.5972	Remote Similarity	NPC163087
0.5942	Remote Similarity	NPC283375
0.5867	Remote Similarity	NPC41481
0.5844	Remote Similarity	NPC473112
0.5775	Remote Similarity	NPC483863
0.5733	Remote Similarity	NPC473673
0.5732	Remote Similarity	NPC483864
0.5714	Remote Similarity	NPC183122
0.5676	Remote Similarity	NPC4341
0.5676	Remote Similarity	NPC479047
0.5676	Remote Similarity	NPC291638
0.5658	Remote Similarity	NPC472574
0.5641	Remote Similarity	NPC607428
0.561	Remote Similarity	NPC184817
0.56	Remote Similarity	NPC139067
0.56	Remote Similarity	NPC43241
0.5541	Remote Similarity	NPC17877
0.5467	Remote Similarity	NPC48017
0.5455	Remote Similarity	NPC479044
0.5455	Remote Similarity	NPC92293
0.5443	Remote Similarity	NPC473613
0.5443	Remote Similarity	NPC473085
0.5405	Remote Similarity	NPC475759
0.5405	Remote Similarity	NPC483879
0.5385	Remote Similarity	NPC266265
0.5366	Remote Similarity	NPC483866
0.5342	Remote Similarity	NPC475429
0.5342	Remote Similarity	NPC476094
0.5316	Remote Similarity	NPC210591
0.5316	Remote Similarity	NPC184747
0.5278	Remote Similarity	NPC481066
0.5263	Remote Similarity	NPC191082
0.5244	Remote Similarity	NPC88593
0.5244	Remote Similarity	NPC14499
0.5233	Remote Similarity	NPC473214
0.52	Remote Similarity	NPC481067
0.52	Remote Similarity	NPC241951
0.52	Remote Similarity	NPC483847
0.5195	Remote Similarity	NPC67777
0.5195	Remote Similarity	NPC471101
0.5195	Remote Similarity	NPC177340
0.5176	Remote Similarity	NPC127026
0.5176	Remote Similarity	NPC483890
0.5135	Remote Similarity	NPC211137
0.5135	Remote Similarity	NPC66761
0.5135	Remote Similarity	NPC483843
0.5128	Remote Similarity	NPC171207
0.5125	Remote Similarity	NPC70716
0.5125	Remote Similarity	NPC97667
0.5067	Remote Similarity	NPC607964
0.5065	Remote Similarity	NPC291599
0.5065	Remote Similarity	NPC246480
0.5062	Remote Similarity	NPC475652

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3742
0.1-0.2	5231
0.2-0.3	177
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