NPASS Compound

Natural Product: NPC471359

Natural Product ID	NPC471359
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Antiarigenin 3-O-Beta-4,6-Dideoxy-D-Allopyranoside
IUPAC Name	(3S,5S,8R,9S,10S,12R,13S,14S,17R)-3-[(2S,3R,4R,6R)-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5,12,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419865
PubChem CID	73356795
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 86 0 0 0 0 0 0 0 0999 V2000 0.1912 1.3243 3.1606 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1773 0.3622 2.5643 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0916 0.1840 1.0593 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7479 -1.0521 0.8734 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8616 -0.9518 -0.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7540 0.2532 0.0543 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0750 1.2679 0.9029 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6074 1.4007 0.5564 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1407 2.4868 1.3380 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3627 1.7481 -0.8649 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7820 1.0004 -1.4945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9005 0.9573 -0.4748 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5145 0.0194 0.6074 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5188 0.1479 1.7177 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7929 0.8126 1.3105 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6903 2.1861 1.4928 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2561 0.4381 -0.0768 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2199 0.7129 -1.1206 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5128 1.8811 -1.8624 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2294 -0.4157 -2.0979 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0092 -1.5497 -1.4251 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5605 -1.0273 -0.1501 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0059 -1.3478 0.0845 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8741 -1.9350 -0.7150 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1858 -2.0516 -0.0798 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2014 -2.5781 -0.6346 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0667 -1.4998 1.1614 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7568 -1.0463 1.3319 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5003 1.2103 -0.4400 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9896 -0.1407 0.5081 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 0.0411 -0.3508 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5702 -1.2369 -0.6259 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9392 -1.1696 -0.8393 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3356 -2.4761 -1.5362 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5948 -1.0755 0.5221 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9372 0.0423 1.2706 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0621 0.8976 0.3819 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7877 1.6896 -0.4793 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9385 0.8618 1.7970 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6132 -0.4585 3.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1733 -1.4527 1.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0749 -1.8640 0.5134 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5427 -1.0904 -1.1741 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4893 -1.8830 0.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9427 0.6558 -0.9872 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 2.2769 0.8150 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1211 0.9106 1.9522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4814 3.3434 1.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1075 2.8438 -0.9847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2354 1.6081 -1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1055 1.5614 -2.4049 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4780 -0.0134 -1.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9297 1.9933 -0.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5973 -1.0189 0.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7721 -0.8316 2.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1391 0.7631 2.5873 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5772 0.4738 2.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0530 2.7367 0.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1110 1.7838 -2.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7988 -0.1636 -3.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2555 -0.7870 -2.4082 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3039 -2.4015 -1.1959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7820 -1.9486 -2.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0367 -1.5100 0.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6526 -2.2854 -1.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8310 0.0569 1.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2829 -1.5274 2.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3355 1.8127 -1.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8471 1.8802 0.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2827 0.4835 -0.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7842 0.4740 -1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2397 -0.3638 -1.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4398 -2.3990 -1.6778 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8736 -2.4397 -2.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0338 -3.3564 -0.9393 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6948 -0.9600 0.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4122 -2.0709 1.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3499 -0.3774 2.1131 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4920 1.5737 1.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2004 2.4152 0.0199 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4751 1.1849 1.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 3 2 1 1 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 17 29 1 6 6 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 13 3 1 0 22 17 1 0 28 23 1 0 37 31 1 0 8 3 1 0 18 12 1 0 2 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 6 7 46 1 0 7 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 1 13 54 1 6 14 55 1 0 14 56 1 0 15 57 1 1 16 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 1 24 65 1 0 28 66 1 0 28 67 1 0 29 68 1 0 29 69 1 0 29 70 1 0 31 71 1 6 33 72 1 6 34 73 1 0 34 74 1 0 34 75 1 0 35 76 1 0 35 77 1 0 36 78 1 1 37 79 1 1 38 80 1 0 39 81 1 0 M END

Standard InCHIKey	XAWYAZSPAYVPBC-UJBLMFSHSA-N
Standard InCHI	InChI=1S/C29H42O10/c1-15-9-21(31)24(34)25(38-15)39-17-3-6-27(14-30)20-11-22(32)26(2)18(16-10-23(33)37-13-16)5-8-29(26,36)19(20)4-7-28(27,35)12-17/h10,14-15,17-22,24-25,31-32,34-36H,3-9,11-13H2,1-2H3/t15-,17+,18-,19-,20+,21-,22-,24-,25+,26+,27+,28+,29+/m1/s1
SMILES	O=C[C@@]12CC[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1C[C@@H](O)[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@@H]1O[C@H](C)C[C@H]([C@H]1O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	550.28	Volume:	538.794 ? Van der Waals volume.
Dense:	1.021	LogP:	0.213 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.938 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.673 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	162.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.192	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.522	Fsp³:	0.862
MCE-18:	116.926 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.643	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.144	Promiscuous compounds:	0.648

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.908	MDCK Permeability:	-5.12
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
PAMPA:	1.0 ? 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%):	0.634	30% Bioavailability (F30%):	0.553
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.746
Plasma Protein Binding (PPB):	30.332%	Volume Distribution (VD):	-0.587
Fu:	75.065% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.909
OATP1B3 inhibitor:	0.904	BCRP inhibitor:	0.015
BSEP inhibitor:	0.232

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:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.005 ? 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):

2.758

Half-life (T1/2):

3.932

ADMET: Toxicity

hERG Blockers:	0.254	hERG Blockers (10um):	0.742
Human Hepatotoxicity (H-HT):	0.691	Drug-induced Liver Injury (DILI):	0.267
AMES Toxicity:	0.846	Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.977	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.999
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.729
Hematotoxicity:	0.387	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.898
A549 Cytotoxicity:	0.72	Hek293 Cytotoxicity:	0.989
BCF:	0.472 ? 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:	3.165 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.721 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.858 ? 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	=	81.6	%	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 NPC471359 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	16180
0.1-0.2	29419
0.2-0.3	3990
0.3-0.4	99
0.4-0.5	105
0.5-0.6	36
0.6-0.7	15
0.7-0.8	0
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC9499
0.8	Intermediate Similarity	NPC471360
0.8	Intermediate Similarity	NPC469751
0.8	Intermediate Similarity	NPC471361
0.8	Intermediate Similarity	NPC86159
0.8	Intermediate Similarity	NPC469752
0.8	Intermediate Similarity	NPC469754
0.8	Intermediate Similarity	NPC70542
0.7059	Intermediate Similarity	NPC469753
0.6824	Remote Similarity	NPC77319
0.6824	Remote Similarity	NPC471351
0.6824	Remote Similarity	NPC471355
0.6667	Remote Similarity	NPC471354
0.6667	Remote Similarity	NPC27507
0.6623	Remote Similarity	NPC469794
0.6395	Remote Similarity	NPC17896
0.6395	Remote Similarity	NPC469755
0.6395	Remote Similarity	NPC284406
0.6395	Remote Similarity	NPC197707
0.6395	Remote Similarity	NPC251866
0.6364	Remote Similarity	NPC179412
0.6364	Remote Similarity	NPC471356
0.6279	Remote Similarity	NPC219085
0.6	Remote Similarity	NPC471353
0.5889	Remote Similarity	NPC180079
0.5789	Remote Similarity	NPC32793
0.5789	Remote Similarity	NPC116075
0.5773	Remote Similarity	NPC469749
0.5667	Remote Similarity	NPC6108
0.5667	Remote Similarity	NPC89514
0.5638	Remote Similarity	NPC173555
0.5625	Remote Similarity	NPC608063
0.5618	Remote Similarity	NPC99728
0.5618	Remote Similarity	NPC87250
0.5618	Remote Similarity	NPC244402
0.5618	Remote Similarity	NPC50305
0.5604	Remote Similarity	NPC10823
0.5556	Remote Similarity	NPC146857
0.5556	Remote Similarity	NPC84987
0.5556	Remote Similarity	NPC247190
0.5506	Remote Similarity	NPC158344
0.5506	Remote Similarity	NPC474418
0.5495	Remote Similarity	NPC157376
0.5495	Remote Similarity	NPC142066
0.5495	Remote Similarity	NPC603972
0.5368	Remote Similarity	NPC488162
0.5368	Remote Similarity	NPC93416
0.5366	Remote Similarity	NPC189588
0.5357	Remote Similarity	NPC196471
0.5354	Remote Similarity	NPC59288
0.5354	Remote Similarity	NPC208193
0.5233	Remote Similarity	NPC475030
0.5192	Remote Similarity	NPC329636
0.5189	Remote Similarity	NPC329675
0.5189	Remote Similarity	NPC194716
0.5161	Remote Similarity	NPC469750
0.5161	Remote Similarity	NPC34390
0.5155	Remote Similarity	NPC474466
0.5106	Remote Similarity	NPC480914
0.5054	Remote Similarity	NPC484211

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6355
0.1-0.2	2714
0.2-0.3	67
0.3-0.4	2
0.4-0.5	6
0.5-0.6	5
0.6-0.7	1
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
0.6395	Remote Similarity	NPD7319	Approved
0.5638	Remote Similarity	NPD8296	Phase 4
0.5543	Remote Similarity	NPD8335	Phase 4
0.5484	Remote Similarity	NPD8380	Approved
0.5149	Remote Similarity	NPD8378	Pre-clinical
0.5149	Remote Similarity	NPD8379	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