NPASS Compound

Natural Product: NPC243196

Natural Product ID	NPC243196
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	19-(Beta-D-Glucosyloxy)-3Beta,5,14-Trihydroxy-5Beta-Card-20(22)-Enolide
IUPAC Name	3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-10-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419864
PubChem CID	73347665
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 89 0 0 0 0 0 0 0 0999 V2000 -3.6277 -2.0168 0.5718 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3160 -1.0631 -0.5767 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0630 -1.5038 -1.3112 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7942 -1.0974 -0.6348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7743 0.4105 -0.3493 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8952 0.6460 0.5791 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8838 2.0045 1.2422 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5774 2.0901 1.9954 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5178 2.0983 0.9548 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2370 3.2901 0.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5227 3.6119 -0.6527 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2811 2.3716 -0.9747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4112 1.1461 -1.0817 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6158 0.8261 0.1551 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2072 -0.2375 0.9927 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3792 -0.2427 1.5808 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5866 -0.2328 1.0117 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7157 0.5036 1.6430 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9567 0.2645 0.7933 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7728 -0.6869 -0.3280 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8742 -1.8505 -0.0087 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6693 -3.1047 0.2420 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8565 -4.1960 0.4542 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0921 -1.6298 1.1110 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3958 -0.0804 -1.5321 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0470 -0.1157 1.6005 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5507 1.8382 1.8927 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 4.4910 0.1638 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6934 2.3371 1.6324 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2119 0.3536 -0.0388 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6077 1.1556 -1.2223 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9735 0.4557 -1.4804 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4944 -0.9667 -1.5000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5460 -1.9837 -1.3147 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7906 -1.7089 -0.9705 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5565 -2.9295 -0.8744 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7951 -3.0423 -0.5648 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6825 -3.9506 -1.1840 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4226 -3.4369 -1.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2653 0.4655 0.8867 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0385 -2.9490 0.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7017 -2.2094 0.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3485 -1.5267 1.5529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0881 -2.6252 -1.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0979 -1.2248 -2.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8614 -1.5751 0.3878 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0379 -1.4374 -1.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9550 1.0090 -1.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7818 -0.0903 1.4324 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0451 2.8291 0.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6950 2.0069 1.9990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4432 1.2158 2.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4863 3.0528 2.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1090 4.1143 0.6599 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 3.0032 -0.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2643 4.2120 -1.5695 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1725 2.2802 -0.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6639 2.5171 -2.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6240 1.4771 -1.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8823 0.3029 -1.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4269 -0.4348 1.8359 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1185 -1.2573 0.4571 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5808 -0.0473 -0.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9211 -0.0578 2.6227 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2422 1.2490 0.3666 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7916 -1.1243 -0.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1797 -2.0139 -0.8659 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3385 -2.9120 1.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3105 -3.3033 -0.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2276 -3.9665 1.1805 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7300 -0.6223 -2.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7805 0.0771 2.5261 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2316 2.0460 2.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6125 5.1574 0.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5852 2.9615 2.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7525 2.2185 -1.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0488 0.9150 -2.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3742 0.7443 -2.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5866 0.7109 -0.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0729 -1.1412 -2.5436 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2320 -0.7288 -0.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2890 -3.6239 -2.6384 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5975 -3.9167 -0.9638 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9629 0.4046 1.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 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 1 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 21 24 1 0 20 25 1 0 19 26 1 0 18 27 1 0 11 28 1 0 9 29 1 1 6 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 30 40 1 1 33 2 1 0 39 34 1 0 30 2 1 0 14 5 1 0 24 17 1 0 14 9 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 3 45 1 0 4 46 1 0 4 47 1 0 5 48 1 6 6 49 1 1 7 50 1 0 7 51 1 0 8 52 1 0 8 53 1 0 10 54 1 0 10 55 1 0 11 56 1 6 12 57 1 0 12 58 1 0 13 59 1 0 13 60 1 0 15 61 1 0 15 62 1 0 17 63 1 6 18 64 1 1 19 65 1 6 20 66 1 6 21 67 1 6 22 68 1 0 22 69 1 0 23 70 1 0 25 71 1 0 26 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 33 80 1 6 35 81 1 0 39 82 1 0 39 83 1 0 40 84 1 0 M END

Standard InCHIKey	KJWPQMICCIJXJF-BETXHDQMSA-N
Standard InCHI	InChI=1S/C29H44O11/c1-26-6-3-18-19(29(26,37)9-5-17(26)15-10-21(32)38-13-15)4-8-28(36)11-16(31)2-7-27(18,28)14-39-25-24(35)23(34)22(33)20(12-30)40-25/h10,16-20,22-25,30-31,33-37H,2-9,11-14H2,1H3/t16-,17+,18-,19+,20+,22+,23-,24+,25+,26+,27-,28-,29-/m0/s1
SMILES	C[C@@]12CC[C@H]3[C@@H](CC[C@@]4(C[C@H](CC[C@]34CO[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O)[C@]2(CC[C@@H]1C1=CC(=O)OC1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.29	Volume:	550.221 ? Van der Waals volume.
Dense:	1.033	LogP:	-0.465 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.556 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.079 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	32.0
TPSA:	186.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.212	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.325	Fsp³:	0.897
MCE-18:	116.291 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.671	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.122	Promiscuous compounds:	0.336

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.428	MDCK Permeability:	-5.286
Pgp-inhibitor:	0.0	Pgp-substrate:	0.994
PAMPA:	0.998 ? 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):	0.08
20% Bioavailability (F20%):	0.748	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.677
Plasma Protein Binding (PPB):	59.857%	Volume Distribution (VD):	-0.435
Fu:	37.684% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.015	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.0 ? 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):

1.366

Half-life (T1/2):

4.358

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.02
Human Hepatotoxicity (H-HT):	0.847	Drug-induced Liver Injury (DILI):	0.141
AMES Toxicity:	0.881	Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.889	Skin Sensitization:	1.0
Carcinogencity:	0.879	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.196
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.976
Hematotoxicity:	0.512	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.735	RPMI-8226 Immunitoxicity:	0.354
A549 Cytotoxicity:	0.823	Hek293 Cytotoxicity:	0.717
BCF:	0.426 ? 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:	3.081 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.55 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.595 ? 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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	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

Activity Type	# Activity
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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	29.4	%	PMID[24033101]

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 NPC243196 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	14870
0.1-0.2	28970
0.2-0.3	5364
0.3-0.4	462
0.4-0.5	91
0.5-0.6	81
0.6-0.7	14
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
0.7625	Intermediate Similarity	NPC146456
0.6829	Remote Similarity	NPC84987
0.6533	Remote Similarity	NPC10232
0.6486	Remote Similarity	NPC97487
0.6264	Remote Similarity	NPC475556
0.6264	Remote Similarity	NPC32793
0.6264	Remote Similarity	NPC116075
0.6264	Remote Similarity	NPC311706
0.6234	Remote Similarity	NPC72772
0.6163	Remote Similarity	NPC5311
0.6163	Remote Similarity	NPC77299
0.6163	Remote Similarity	NPC480906
0.6092	Remote Similarity	NPC480914
0.6022	Remote Similarity	NPC475629
0.6	Remote Similarity	NPC480907
0.5977	Remote Similarity	NPC157376
0.5977	Remote Similarity	NPC142066
0.5977	Remote Similarity	NPC603972
0.593	Remote Similarity	NPC99728
0.593	Remote Similarity	NPC87250
0.593	Remote Similarity	NPC244402
0.593	Remote Similarity	NPC50305
0.5895	Remote Similarity	NPC469749
0.587	Remote Similarity	NPC30483
0.587	Remote Similarity	NPC470897
0.5851	Remote Similarity	NPC610296
0.5833	Remote Similarity	NPC146857
0.5833	Remote Similarity	NPC247190
0.5814	Remote Similarity	NPC158344
0.5806	Remote Similarity	NPC236973
0.5806	Remote Similarity	NPC32177
0.5806	Remote Similarity	NPC469756
0.5806	Remote Similarity	NPC275901
0.5795	Remote Similarity	NPC17896
0.5795	Remote Similarity	NPC469755
0.5795	Remote Similarity	NPC284406
0.5795	Remote Similarity	NPC197707
0.5795	Remote Similarity	NPC251866
0.5745	Remote Similarity	NPC188234
0.5682	Remote Similarity	NPC219085
0.5638	Remote Similarity	NPC292467
0.5625	Remote Similarity	NPC125077
0.5588	Remote Similarity	NPC329675
0.5588	Remote Similarity	NPC194716
0.5579	Remote Similarity	NPC480910
0.5579	Remote Similarity	NPC240070
0.5579	Remote Similarity	NPC480909
0.5556	Remote Similarity	NPC76572
0.5556	Remote Similarity	NPC193382
0.5521	Remote Similarity	NPC264336
0.5464	Remote Similarity	NPC59288
0.5464	Remote Similarity	NPC486143
0.5464	Remote Similarity	NPC486135
0.5464	Remote Similarity	NPC486142
0.5464	Remote Similarity	NPC486137
0.5464	Remote Similarity	NPC486149
0.5446	Remote Similarity	NPC475590
0.5432	Remote Similarity	NPC222875
0.5432	Remote Similarity	NPC25177
0.5408	Remote Similarity	NPC232785
0.5408	Remote Similarity	NPC486139
0.54	Remote Similarity	NPC476221
0.54	Remote Similarity	NPC477709
0.5393	Remote Similarity	NPC99620
0.5385	Remote Similarity	NPC604978
0.5354	Remote Similarity	NPC329986
0.5354	Remote Similarity	NPC140092
0.5354	Remote Similarity	NPC486146
0.5333	Remote Similarity	NPC196429
0.5333	Remote Similarity	NPC309034
0.53	Remote Similarity	NPC486138
0.53	Remote Similarity	NPC276838
0.5294	Remote Similarity	NPC486144
0.5294	Remote Similarity	NPC486145
0.5294	Remote Similarity	NPC486147
0.5294	Remote Similarity	NPC486136
0.5294	Remote Similarity	NPC486148
0.5275	Remote Similarity	NPC469750
0.5275	Remote Similarity	NPC480915
0.5258	Remote Similarity	NPC486130
0.5258	Remote Similarity	NPC608063
0.5204	Remote Similarity	NPC486127
0.5192	Remote Similarity	NPC120390
0.5192	Remote Similarity	NPC74259
0.5192	Remote Similarity	NPC475419
0.5185	Remote Similarity	NPC268829
0.5185	Remote Similarity	NPC295110
0.5143	Remote Similarity	NPC474908
0.5143	Remote Similarity	NPC486134
0.5143	Remote Similarity	NPC486141
0.5122	Remote Similarity	NPC480913
0.5111	Remote Similarity	NPC474418
0.5098	Remote Similarity	NPC486132
0.5098	Remote Similarity	NPC486131
0.5094	Remote Similarity	NPC486150
0.5049	Remote Similarity	NPC486128

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC243196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6006
0.1-0.2	2996
0.2-0.3	131
0.3-0.4	8
0.4-0.5	6
0.5-0.6	1
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
0.5795	Remote Similarity	NPD7319	Approved

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