NPASS Compound

Natural Product: NPC96903

Natural Product ID	NPC96903
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NQIMWYUGXRUKFK-IAXXPUDGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1829518
PubChem CID	56642790
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 82 86 0 0 0 0 0 0 0 0999 V2000 -3.8278 -1.1874 -3.2212 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3879 -1.1433 -2.8413 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5017 -1.2910 -3.7471 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0365 -0.9418 -1.5044 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6194 -0.9178 -1.2570 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3487 -0.6944 0.2175 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9764 0.6337 0.5332 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3616 0.6676 0.5543 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1662 1.3992 -0.2981 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5495 2.0715 -1.1441 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6142 1.4530 -0.2962 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4293 0.7798 0.5839 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8089 0.8981 0.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4231 1.6809 -0.4572 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6133 2.3525 -1.3348 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2478 2.2309 -1.2430 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2614 1.3610 1.6420 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1784 1.4989 1.2654 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5631 0.6956 0.0022 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1735 -0.6400 0.4853 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3765 -0.5948 1.8860 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9110 0.5942 2.2528 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3489 0.8033 2.3194 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3244 0.9457 3.6348 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8820 -1.8351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1130 -3.1337 -0.0245 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2665 -3.1229 0.4777 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7919 -1.8364 1.0604 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1690 -1.9364 1.3077 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6764 -1.8956 2.6062 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8585 -1.7601 3.5504 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1124 -2.0029 2.9448 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1149 -3.5650 -0.5690 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5906 -1.6482 -1.3245 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9642 -2.1396 0.8853 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9526 0.8975 -0.1777 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4411 1.4944 -1.3280 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6070 1.8479 -2.2007 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8540 1.7319 -1.5781 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8496 1.3849 -0.6924 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2022 1.6266 -0.9610 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5872 2.2288 -2.1381 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5998 2.5809 -3.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2600 2.3343 -2.7522 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0010 -0.6723 -4.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0943 -2.2659 -3.3116 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3993 -0.6720 -2.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2804 -0.0523 -1.8694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1223 -1.7825 -1.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7326 1.3246 -0.3423 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9500 0.1804 1.3178 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4382 0.3673 1.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5036 1.7721 -0.5236 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0961 2.9743 -2.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6630 2.7964 -1.9776 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6957 2.3806 1.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4860 0.8310 2.5614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5661 2.5080 1.2387 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0937 1.0785 -0.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0442 0.1088 1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6796 0.9239 3.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5888 1.8153 1.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8169 1.9079 3.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1690 1.0573 4.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6926 0.1572 4.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6569 -3.9478 0.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2082 -3.6238 -1.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4216 -3.8879 1.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2996 -1.7001 2.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4319 -1.0104 3.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1930 -2.7274 3.8003 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7299 -2.3273 2.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9459 -3.9468 -0.1960 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6123 -2.6381 -1.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0842 -0.9620 -2.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6542 -1.3789 -1.1729 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5134 -2.8244 0.4375 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5461 0.9138 0.2278 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9639 1.3350 -0.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6332 2.4128 -2.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8661 3.0556 -3.9672 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4791 2.6120 -3.4580 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 21 22 1 0 22 23 1 0 22 24 1 0 20 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 27 33 1 0 25 34 1 0 25 35 1 1 19 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 28 6 1 0 44 39 1 0 20 6 1 0 16 11 1 0 22 18 1 0 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 0 5 49 1 0 7 50 1 6 12 51 1 0 13 52 1 0 14 53 1 0 15 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 6 19 59 1 6 23 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 24 65 1 0 26 66 1 0 26 67 1 0 27 68 1 1 28 69 1 1 32 70 1 0 32 71 1 0 32 72 1 0 33 73 1 0 34 74 1 0 34 75 1 0 34 76 1 0 35 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 43 81 1 0 44 82 1 0 M END

Standard InCHIKey	NQIMWYUGXRUKFK-IAXXPUDGSA-N
Standard InCHI	InChI=1S/C33H38O11/c1-19(34)40-18-32-25(42-28(37)21-12-8-6-9-13-21)16-23-26(43-29(38)22-14-10-7-11-15-22)33(32,44-30(23,3)4)31(5,39)17-24(36)27(32)41-20(2)35/h6-15,23-27,36,39H,16-18H2,1-5H3/t23-,24+,25+,26-,27+,31+,32-,33+/m1/s1
SMILES	CC(=O)OC[C@@]12[C@@H](OC(=O)c3ccccc3)C[C@@H]3[C@H]([C@]2(OC3(C)C)[C@@](C[C@@H]([C@@H]1OC(=O)C)O)(C)O)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.24	Volume:	606.87 ? Van der Waals volume.
Dense:	1.006	LogP:	2.565 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.581 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.277 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	30.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.351	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.778	Fsp³:	0.515
MCE-18:	168.72 ? 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:	0.356	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.12 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.053	Promiscuous compounds:	0.113

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.686	MDCK Permeability:	-5.095
Pgp-inhibitor:	0.865	Pgp-substrate:	0.595
PAMPA:	0.753 ? 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%):	0.003	30% Bioavailability (F30%):	0.047
50% Bioavailability (F50%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.655	MRP1:	1.0
Plasma Protein Binding (PPB):	84.512%	Volume Distribution (VD):	-0.256
Fu:	15.628% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.958	BCRP inhibitor:	0.005
BSEP inhibitor:	0.866

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? 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):

1.772

Half-life (T1/2):

1.452

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.443
Human Hepatotoxicity (H-HT):	0.042	Drug-induced Liver Injury (DILI):	0.529
AMES Toxicity:	0.795	Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.274	Skin Sensitization:	0.994
Carcinogencity:	0.856	Eye Corrosion:	0.0
Eye Irritation:	0.404	Respiratory Toxicity:	0.045
Drug-induced Neurotoxicity:	0.571	Ototoxicity:	0.26
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.661
Genotoxicity:	0.267	RPMI-8226 Immunitoxicity:	0.07
A549 Cytotoxicity:	0.341	Hek293 Cytotoxicity:	0.647
BCF:	0.573 ? 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:	3.635 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.322 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.656 ? 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
Inhibition	1
Ki	1
Imax	1
Ratio IC50	6
Activity	2

Activity Type	# Activity
Cell line	2
Individual protein	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	70.0	%	PMID[16643064]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	470.0	nM	PMID[25621853]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Imax	>	90.0	%	PMID[21856049]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	2.21	n.a.	PMID[21700368]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	6.25	n.a.	PMID[26034885]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	8.82	n.a.	PMID[12444709]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	2.55	n.a.	PMID[18640035]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	13.26	n.a.	PMID[25211032]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	36.6	n.a.	PMID[16872140]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	84.38	%	PMID[16872140]
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	104.77	%	PMID[4851320]

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 NPC96903 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	11473
0.1-0.2	35294
0.2-0.3	2385
0.3-0.4	525
0.4-0.5	122
0.5-0.6	44
0.6-0.7	12
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	Natural Product ID
0.7324	Intermediate Similarity	NPC171207
0.726	Intermediate Similarity	NPC95265
0.6986	Remote Similarity	NPC41481
0.68	Remote Similarity	NPC70716
0.68	Remote Similarity	NPC97667
0.6753	Remote Similarity	NPC481486
0.6667	Remote Similarity	NPC266265
0.6623	Remote Similarity	NPC479042
0.6235	Remote Similarity	NPC176413
0.6235	Remote Similarity	NPC483885
0.6235	Remote Similarity	NPC294512
0.6234	Remote Similarity	NPC57628
0.622	Remote Similarity	NPC610134
0.6	Remote Similarity	NPC17877
0.5977	Remote Similarity	NPC483868
0.5921	Remote Similarity	NPC191082
0.5921	Remote Similarity	NPC200471
0.5921	Remote Similarity	NPC472575
0.5862	Remote Similarity	NPC479045
0.5844	Remote Similarity	NPC270590
0.5714	Remote Similarity	NPC246480
0.5714	Remote Similarity	NPC4341
0.5714	Remote Similarity	NPC479047
0.5714	Remote Similarity	NPC291638
0.5641	Remote Similarity	NPC27377
0.5625	Remote Similarity	NPC472570
0.5513	Remote Similarity	NPC48017
0.55	Remote Similarity	NPC479044
0.55	Remote Similarity	NPC92293
0.5488	Remote Similarity	NPC472568
0.5443	Remote Similarity	NPC67777
0.5443	Remote Similarity	NPC158663
0.5443	Remote Similarity	NPC177340
0.5432	Remote Similarity	NPC472569
0.5432	Remote Similarity	NPC16912
0.5294	Remote Similarity	NPC6815
0.525	Remote Similarity	NPC139067
0.525	Remote Similarity	NPC43241
0.5244	Remote Similarity	NPC11685
0.5238	Remote Similarity	NPC481489
0.519	Remote Similarity	NPC163087
0.5181	Remote Similarity	NPC127720
0.5181	Remote Similarity	NPC184747
0.5176	Remote Similarity	NPC481488
0.5132	Remote Similarity	NPC283375
0.5132	Remote Similarity	NPC183122
0.5125	Remote Similarity	NPC291599
0.5125	Remote Similarity	NPC163719
0.5125	Remote Similarity	NPC95810
0.5122	Remote Similarity	NPC306146
0.5122	Remote Similarity	NPC483841
0.5119	Remote Similarity	NPC282239
0.5119	Remote Similarity	NPC471102
0.5119	Remote Similarity	NPC476970
0.5114	Remote Similarity	NPC56953
0.5062	Remote Similarity	NPC483846
0.5056	Remote Similarity	NPC75600
0.5056	Remote Similarity	NPC483884

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC96903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3295
0.1-0.2	5629
0.2-0.3	226
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