NPASS Compound

Natural Product: NPC270590

Natural Product ID	NPC270590
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DVDRLVPFIGHWDV-XIWIUEAYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1076609
PubChem CID	46185848
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 89 94 0 0 0 0 0 0 0 0999 V2000 -0.8889 5.0720 2.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0301 3.6030 2.6024 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0260 3.0204 3.1458 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0868 2.8061 2.0207 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1484 1.3661 1.9843 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0317 0.7902 2.6120 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6348 -0.4458 2.0179 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4231 -1.6719 2.8729 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2770 -0.5988 0.5838 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7096 -1.8464 -0.0740 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8130 -1.3249 -1.5264 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4688 -0.9592 -2.0430 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6072 -0.9983 -0.9784 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2131 -0.4078 0.3250 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0683 -1.1059 1.3652 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4015 1.0463 0.5239 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6485 1.5807 0.1902 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7896 2.6608 -0.6844 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7255 3.1219 -1.1614 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0726 3.2409 -1.0409 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0922 4.3012 -1.9184 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2577 4.9209 -2.3151 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4580 4.4640 -1.8153 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4334 3.3880 -0.9254 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2580 2.7802 -0.5395 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8111 -0.5774 -1.5328 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8935 -1.4360 -1.7349 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7180 -2.6466 -1.3689 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1607 -1.0512 -2.3149 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1695 -1.9771 -2.4298 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4023 -1.6279 -2.9976 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6278 -0.3559 -3.4502 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6219 0.5792 -3.3392 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4008 0.2184 -2.7727 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -0.0080 -1.2092 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0220 -0.2542 -1.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3111 1.0028 -2.3200 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9621 0.4550 -0.0750 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0105 -2.1705 0.3862 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3518 -3.4431 0.8500 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4401 -4.2990 0.8404 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6846 -3.7632 1.3180 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7038 -2.8447 1.3400 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9638 -3.2121 1.8009 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2324 -4.4886 2.2450 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2082 -5.4067 2.2214 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9508 -5.0368 1.7605 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0424 -0.2345 2.0400 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9958 1.8104 2.7985 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0973 5.3296 3.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8387 5.5699 2.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6296 5.3802 1.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0981 1.1315 2.5185 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7615 0.5111 3.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9049 -2.4986 2.3477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9308 -1.4158 3.8599 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3916 -2.1372 3.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0162 -2.6794 -0.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4059 -1.9868 -2.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1835 -1.7478 -2.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3886 -0.0090 -2.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7397 -2.1099 -0.7796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1484 -2.2093 1.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1174 -0.7300 1.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8541 -0.8684 2.3927 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4005 1.6118 -0.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1663 4.7096 -2.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2675 5.7529 -3.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3872 4.9385 -2.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3928 3.0515 -0.5497 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2430 1.9402 0.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0888 -3.0068 -2.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1958 -2.3753 -3.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5790 -0.0532 -3.8978 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7954 1.5808 -3.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6402 0.9772 -2.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5805 0.2983 -1.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2216 -1.3270 -1.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5206 0.0322 -0.2428 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4577 1.6720 -2.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2116 1.6878 -2.3470 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3056 0.5206 -3.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5487 -1.8322 1.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7311 -2.4373 1.7935 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2376 -4.7332 2.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3930 -6.4151 2.5644 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1588 -5.7669 1.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2706 -0.0831 2.9852 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4968 1.6899 3.6347 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 7 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 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 13 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 11 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 10 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 46 47 2 0 7 48 1 6 6 49 1 0 16 5 1 0 25 20 1 0 34 29 1 0 47 42 1 0 14 9 1 0 9 38 1 6 1 50 1 0 1 51 1 0 1 52 1 0 5 53 1 1 6 54 1 1 8 55 1 0 8 56 1 0 8 57 1 0 10 58 1 6 11 59 1 6 12 60 1 0 12 61 1 0 13 62 1 1 15 63 1 0 15 64 1 0 15 65 1 0 16 66 1 6 21 67 1 0 22 68 1 0 23 69 1 0 24 70 1 0 25 71 1 0 30 72 1 0 31 73 1 0 32 74 1 0 33 75 1 0 34 76 1 0 36 77 1 0 36 78 1 0 36 79 1 0 37 80 1 0 37 81 1 0 37 82 1 0 43 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 47 87 1 0 48 88 1 0 49 89 1 0 M END

Standard InCHIKey	DVDRLVPFIGHWDV-XIWIUEAYSA-N
Standard InCHI	InChI=1S/C38H40O11/c1-22(39)45-28-29(40)37(5,44)38-30(47-33(42)24-17-11-7-12-18-24)26(35(2,3)49-38)21-27(46-32(41)23-15-9-6-10-16-23)36(38,4)31(28)48-34(43)25-19-13-8-14-20-25/h6-20,26-31,40,44H,21H2,1-5H3/t26-,27+,28-,29+,30-,31+,36-,37+,38-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@@H]([C@@](C)([C@@]23[C@@H]([C@@H](C[C@@H]([C@]2(C)[C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)C(C)(C)O3)OC(=O)c1ccccc1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	672.26	Volume:	676.884 ? Van der Waals volume.
Dense:	0.993	LogP:	3.807 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.314 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.139 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	36.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.273	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.811	Fsp³:	0.421
MCE-18:	189.519 ? 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:	0.732	Fluc inhibitor:	0.04 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.168 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.147	Promiscuous compounds:	0.152

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.604	MDCK Permeability:	-4.909
Pgp-inhibitor:	1.0	Pgp-substrate:	0.552
PAMPA:	0.852 ? 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%):	0.023	30% Bioavailability (F30%):	0.289
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	1.0
Plasma Protein Binding (PPB):	94.186%	Volume Distribution (VD):	-0.384
Fu:	7.152% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.971	BCRP inhibitor:	0.036
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.644
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.088	CYP3A4-substrate:	0.777
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.994 ? 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):

5.404

Half-life (T1/2):

0.735

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.611
Human Hepatotoxicity (H-HT):	0.047	Drug-induced Liver Injury (DILI):	0.575
AMES Toxicity:	0.127	Rat Oral Acute Toxicity:	0.164
Maximum Recommended Daily Dose:	0.334	Skin Sensitization:	0.985
Carcinogencity:	0.491	Eye Corrosion:	0.0
Eye Irritation:	0.286	Respiratory Toxicity:	0.077
Drug-induced Neurotoxicity:	0.27	Ototoxicity:	0.423
Hematotoxicity:	0.011	Drug-induced Nephrotoxicity:	0.784
Genotoxicity:	0.444	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.051	Hek293 Cytotoxicity:	0.216
BCF:	0.905 ? 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:	4.089 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.364 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.041 ? 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[19093848]
NPT2	Others	Unspecified	n.a.	Activity	=	13.7	%	PMID[21489793]
NPT2	Others	Unspecified	n.a.	Activity	=	54.2	%	Open TG-GATES in vivo data: Organ Weight
NPT2	Others	Unspecified	n.a.	Activity	=	87.1	%	PMID[21634430]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[18809945]

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 NPC270590 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	12108
0.1-0.2	34892
0.2-0.3	2196
0.3-0.4	483
0.4-0.5	120
0.5-0.6	43
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9344	High Similarity	NPC158663
0.7432	Intermediate Similarity	NPC184817
0.6714	Remote Similarity	NPC483883
0.6714	Remote Similarity	NPC151585
0.6125	Remote Similarity	NPC56953
0.6053	Remote Similarity	NPC95265
0.5854	Remote Similarity	NPC483870
0.5854	Remote Similarity	NPC127026
0.5854	Remote Similarity	NPC483890
0.5844	Remote Similarity	NPC96903
0.5775	Remote Similarity	NPC200592
0.5775	Remote Similarity	NPC270498
0.5775	Remote Similarity	NPC610542
0.5676	Remote Similarity	NPC163087
0.5641	Remote Similarity	NPC127720
0.5641	Remote Similarity	NPC70716
0.5641	Remote Similarity	NPC97667
0.5634	Remote Similarity	NPC283375
0.56	Remote Similarity	NPC163719
0.56	Remote Similarity	NPC95810
0.5556	Remote Similarity	NPC473081
0.5556	Remote Similarity	NPC195647
0.5541	Remote Similarity	NPC483879
0.55	Remote Similarity	NPC479042
0.5455	Remote Similarity	NPC171207
0.5455	Remote Similarity	NPC473673
0.5422	Remote Similarity	NPC174982
0.5422	Remote Similarity	NPC483865
0.5417	Remote Similarity	NPC183122
0.5417	Remote Similarity	NPC474608
0.5385	Remote Similarity	NPC92293
0.5357	Remote Similarity	NPC188865
0.5357	Remote Similarity	NPC610134
0.5325	Remote Similarity	NPC471101
0.5325	Remote Similarity	NPC472572
0.5316	Remote Similarity	NPC266265
0.5263	Remote Similarity	NPC281717
0.5263	Remote Similarity	NPC483886
0.5227	Remote Similarity	NPC176413
0.5227	Remote Similarity	NPC483885
0.5227	Remote Similarity	NPC294512
0.5195	Remote Similarity	NPC200471
0.5195	Remote Similarity	NPC472575
0.5172	Remote Similarity	NPC483869
0.5128	Remote Similarity	NPC67777
0.5128	Remote Similarity	NPC27377
0.5128	Remote Similarity	NPC177340
0.5059	Remote Similarity	NPC610927
0.5056	Remote Similarity	NPC479045

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC270590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3800
0.1-0.2	5169
0.2-0.3	180
0.3-0.4	1
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