NPASS Compound

Natural Product: NPC483868

Natural Product ID	NPC483868
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZVQABXNRQMXWGL-DZQUJVLKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134134450
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 84 88 0 0 0 0 0 0 0 0999 V2000 -3.6595 -0.6854 -4.3837 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3374 -0.9766 -3.8198 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4909 -1.6555 -4.4261 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0138 -0.4765 -2.5592 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7112 -0.7573 -1.9914 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6143 -0.0932 -0.6247 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8019 1.3935 -0.8742 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4337 2.1475 -1.1755 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6641 1.7321 -0.4462 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7832 0.2272 -0.7897 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6962 -0.2663 0.0642 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9188 -1.6308 0.6550 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2116 -2.7150 -0.3185 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1747 -1.9916 1.5875 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3924 -1.1468 1.5513 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7754 -0.6299 0.1849 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3373 -1.7489 -0.4859 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6712 -1.8326 -0.8299 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4244 -0.8918 -0.5450 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1262 -3.0611 -1.5294 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4405 -0.1640 2.5678 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3363 -0.1412 3.6129 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1945 -1.0843 3.6672 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3360 0.9236 4.6583 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0926 -1.4818 1.4418 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6297 0.5946 1.1913 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4846 1.6379 1.0312 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7905 2.8770 1.6143 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7534 1.4943 1.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0586 -0.2610 -0.5306 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8776 -0.7040 -1.5577 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3995 -0.6365 -2.7231 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1995 -1.2196 -1.3737 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9462 -1.6374 -2.4476 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2349 -2.1433 -2.2964 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7748 -2.2259 -1.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0544 -1.8184 0.0488 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7721 -1.3176 -0.1256 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6064 2.0034 0.1288 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8612 2.5296 -0.1053 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3060 2.4558 -1.2762 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6830 3.1549 0.9132 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3698 3.3335 2.2364 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4435 3.9669 2.8153 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3714 4.1494 1.8167 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8763 3.6578 0.7305 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7424 -1.1775 -5.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8320 0.4235 -4.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5034 -1.0462 -3.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0554 -0.2971 -2.7571 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6558 -1.8427 -1.9670 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4491 1.4706 -1.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1988 3.2274 -1.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6734 1.9888 -2.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5201 2.2923 -0.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6097 0.1707 -1.8729 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0149 -3.3823 0.1114 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5674 -2.4140 -1.2970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3636 -3.4138 -0.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4548 -3.0667 1.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1553 -2.0287 2.6690 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2509 -1.8378 1.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5645 0.1422 0.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3574 -3.3894 -2.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0668 -2.9186 -2.0885 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2068 -3.8596 -0.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1944 1.6092 4.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4206 0.3915 5.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3875 1.4696 4.6948 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0012 -1.9561 2.2935 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4851 3.4505 2.2990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0388 2.5667 2.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4972 3.5996 0.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1211 2.5250 2.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5897 1.0075 1.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4788 1.0342 2.7963 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5246 -1.5719 -3.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8423 -2.4781 -3.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7786 -2.6196 -0.9075 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4645 -1.8783 1.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2318 -1.0060 0.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 3.0243 2.6805 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5564 4.2730 3.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3450 4.6334 1.9705 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 6 5 1 6 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 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 12 25 1 1 11 26 1 1 26 27 1 0 27 28 1 0 27 29 1 0 10 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 7 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 16 6 1 0 38 33 1 0 46 42 1 0 11 6 1 0 27 9 1 0 1 47 1 0 1 48 1 0 1 49 1 0 5 50 1 0 5 51 1 0 7 52 1 6 8 53 1 0 8 54 1 0 9 55 1 1 10 56 1 6 13 57 1 0 13 58 1 0 13 59 1 0 14 60 1 0 14 61 1 0 15 62 1 1 16 63 1 1 20 64 1 0 20 65 1 0 20 66 1 0 24 67 1 0 24 68 1 0 24 69 1 0 25 70 1 0 28 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 29 75 1 0 29 76 1 0 34 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 38 81 1 0 43 82 1 0 44 83 1 0 45 84 1 0 M END

Standard InCHIKey	ZVQABXNRQMXWGL-DZQUJVLKSA-N
Standard InCHI	InChI=1S/C33H38O13/c1-18(34)41-17-32-25(44-29(38)23-13-10-14-40-23)15-22-26(45-28(37)21-11-8-7-9-12-21)33(32,46-30(22,4)5)31(6,39)16-24(42-19(2)35)27(32)43-20(3)36/h7-14,22,24-27,39H,15-17H2,1-6H3/t22-,24-,25+,26-,27+,31+,32-,33+/m1/s1
SMILES	CC(=O)OC[C@@]12[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)(C[C@H]([C@@H]1OC(=O)C)OC(=O)C)O)OC3(C)C)OC(=O)c1ccccc1)OC(=O)c1ccco1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	642.23	Volume:	624.45 ? Van der Waals volume.
Dense:	1.028	LogP:	2.582 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.829 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.185 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	30.0
TPSA:	174.1 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.329	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.98	Fsp³:	0.545
MCE-18:	172.824 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.191	Fluc inhibitor:	0.042 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.083 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.07	Promiscuous compounds:	0.108

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.311	MDCK Permeability:	-4.702
Pgp-inhibitor:	0.999	Pgp-substrate:	0.766
PAMPA:	0.447 ? 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%):	0.318	30% Bioavailability (F30%):	0.912
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044	MRP1:	0.999
Plasma Protein Binding (PPB):	72.216%	Volume Distribution (VD):	-0.398
Fu:	27.161% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.026
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.023
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.995 ? 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):

1.251

Half-life (T1/2):

1.264

ADMET: Toxicity

hERG Blockers:	0.048	hERG Blockers (10um):	0.218
Human Hepatotoxicity (H-HT):	0.069	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.794	Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.312	Skin Sensitization:	0.957
Carcinogencity:	0.907	Eye Corrosion:	0.001
Eye Irritation:	0.435	Respiratory Toxicity:	0.045
Drug-induced Neurotoxicity:	0.17	Ototoxicity:	0.254
Hematotoxicity:	0.061	Drug-induced Nephrotoxicity:	0.62
Genotoxicity:	0.664	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.122	Hek293 Cytotoxicity:	0.358
BCF:	0.587 ? 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:	3.545 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.254 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.701 ? 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	2

Activity Type	# Activity
Others	2

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.	Activity	=	81.9	%	PMID[27541714]
NPT2	Others	Unspecified	n.a.	Activity	>	60.0	%	PMID[27541714]

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 NPC483868 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	14628
0.1-0.2	33120
0.2-0.3	1648
0.3-0.4	284
0.4-0.5	126
0.5-0.6	33
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8052	Intermediate Similarity	NPC95265
0.7765	Intermediate Similarity	NPC294512
0.7711	Intermediate Similarity	NPC483870
0.7595	Intermediate Similarity	NPC97667
0.759	Intermediate Similarity	NPC610134
0.7558	Intermediate Similarity	NPC483885
0.7529	Intermediate Similarity	NPC483869
0.7356	Intermediate Similarity	NPC176413
0.716	Intermediate Similarity	NPC70716
0.6988	Remote Similarity	NPC479042
0.6824	Remote Similarity	NPC6815
0.6593	Remote Similarity	NPC479045
0.6235	Remote Similarity	NPC472570
0.6222	Remote Similarity	NPC483874
0.6067	Remote Similarity	NPC14499
0.6047	Remote Similarity	NPC11685
0.6047	Remote Similarity	NPC16912
0.5977	Remote Similarity	NPC96903
0.5889	Remote Similarity	NPC88593
0.587	Remote Similarity	NPC479041
0.587	Remote Similarity	NPC56953
0.5843	Remote Similarity	NPC481489
0.5814	Remote Similarity	NPC171207
0.5806	Remote Similarity	NPC75600
0.5806	Remote Similarity	NPC483884
0.5778	Remote Similarity	NPC476035
0.5761	Remote Similarity	NPC479048
0.5714	Remote Similarity	NPC479049
0.5682	Remote Similarity	NPC472569
0.5604	Remote Similarity	NPC481488
0.5604	Remote Similarity	NPC483875
0.5581	Remote Similarity	NPC479047
0.5581	Remote Similarity	NPC191082
0.5581	Remote Similarity	NPC291638
0.5556	Remote Similarity	NPC282239
0.5556	Remote Similarity	NPC472568
0.5435	Remote Similarity	NPC475039
0.5402	Remote Similarity	NPC4341
0.5393	Remote Similarity	NPC479044
0.5341	Remote Similarity	NPC177340
0.5217	Remote Similarity	NPC471102
0.5217	Remote Similarity	NPC481490
0.5169	Remote Similarity	NPC67777
0.5169	Remote Similarity	NPC43241
0.5165	Remote Similarity	NPC57628
0.5161	Remote Similarity	NPC609309
0.5155	Remote Similarity	NPC483871
0.5109	Remote Similarity	NPC127720
0.5106	Remote Similarity	NPC481487
0.505	Remote Similarity	NPC483873

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483868 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2781
0.1-0.2	6211
0.2-0.3	154
0.3-0.4	4
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