NPASS Compound

Natural Product: NPC471353

Natural Product ID	NPC471353
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Antiaroside X
IUPAC Name	3-[(3S,5R,8R,9S,10R,12R,13S,14S,17R)-12,14-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419851
PubChem CID	73349183
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 83 88 0 0 0 0 0 0 0 0999 V2000 -7.3918 2.3946 0.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5010 1.1969 0.2005 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4072 0.0914 -0.2255 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7917 -1.2698 -0.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9170 -1.4187 1.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 -0.2293 1.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8106 0.8839 1.3611 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2206 -0.0738 0.0542 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8559 -0.1089 0.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2360 -1.3349 -0.4666 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8089 -1.3733 -0.0493 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0639 -0.1592 -0.6192 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6841 1.0003 0.1454 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1485 1.1621 -0.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1237 2.2368 -0.0264 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4151 2.0424 0.7493 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8460 0.6083 0.8235 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3928 -0.2035 -0.3781 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2909 0.1754 -1.5013 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7028 -0.3361 -1.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2592 0.4510 -0.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2628 0.4236 1.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4690 -0.9277 1.8125 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8990 -1.2875 1.4966 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4394 -0.1164 0.6893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6335 -0.4774 -0.0090 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9870 -0.3739 -1.2567 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3446 -0.9015 -1.4842 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9483 -0.9277 -2.6135 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7998 -1.3402 -0.2694 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8148 -1.1147 0.6854 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6581 1.3925 2.0737 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5525 1.8913 -0.3111 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4468 -1.6458 -0.6481 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3769 -0.0628 -2.0711 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0184 -1.1704 -2.8087 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2611 -2.6230 1.0186 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8513 -2.1944 -0.0486 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9067 0.3122 -1.4999 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2294 2.0839 1.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7229 3.1175 1.0875 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7179 2.9083 -0.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7837 1.4617 -0.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2917 0.0791 0.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2765 -1.4922 -1.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5899 -1.3980 1.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4455 -0.3761 2.1110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6716 -0.2751 1.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7287 -2.2274 0.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4211 -1.4110 -1.5489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2846 -2.3126 -0.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7754 -1.2425 1.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6322 0.7197 1.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2802 1.5692 -1.1273 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5156 1.9193 0.6174 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4782 3.0801 0.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3182 2.5403 -1.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1358 2.7401 0.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1834 2.4058 1.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2666 0.1581 1.6888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6428 -1.2745 -0.1128 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0746 -0.2918 -2.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2946 1.2945 -1.5593 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2352 -0.3467 -2.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7270 -1.6775 1.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4140 -0.7965 2.9319 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9498 -2.2400 0.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5161 -1.4113 2.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6671 0.6538 1.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4386 0.0376 -2.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2368 -0.3934 1.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5016 -2.0184 1.2381 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5492 1.0273 2.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9822 2.3234 -1.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6371 2.0354 -0.6054 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4869 2.4743 0.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3060 -2.2715 -1.3802 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4319 0.1647 -2.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1887 0.8000 -2.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7544 -1.6127 -3.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8994 -2.7656 1.9217 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7254 -1.7787 -0.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1684 -0.5727 -1.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 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 13 15 1 0 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 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 22 32 1 0 21 33 1 0 20 34 1 0 12 35 1 0 35 36 1 0 5 37 1 0 4 38 1 0 3 39 1 0 7 2 1 0 14 9 1 0 18 12 1 0 22 17 1 0 25 21 1 0 31 26 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 3 44 1 0 4 45 1 0 5 46 1 0 6 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 27 70 1 0 31 71 1 0 31 72 1 0 32 73 1 0 33 74 1 0 33 75 1 0 33 76 1 0 34 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 37 81 1 0 38 82 1 0 39 83 1 0 M END

Standard InCHIKey	XKSBWDXNRFPBGG-WIZGEALKSA-N
Standard InCHI	InChI=1S/C29H44O10/c1-14-23(33)24(34)25(35)26(38-14)39-17-5-7-28(13-30)16(10-17)3-4-19-20(28)11-21(31)27(2)18(6-8-29(19,27)36)15-9-22(32)37-12-15/h9,14,16-21,23-26,30-31,33-36H,3-8,10-13H2,1-2H3/t14-,16-,17+,18-,19-,20+,21-,23+,24-,25-,26+,27+,28-,29+/m1/s1
SMILES	CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.29	Volume:	541.431 ? Van der Waals volume.
Dense:	1.02	LogP:	-0.695 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.012 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.902 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	10.0

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:	5.389	Fsp³:	0.897
MCE-18:	113.455 ? 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:	0.008	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.074 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.086	Promiscuous compounds:	0.009

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.575	MDCK Permeability:	-5.093
Pgp-inhibitor:	0.0	Pgp-substrate:	0.995
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):	0.993
20% Bioavailability (F20%):	0.851	30% Bioavailability (F30%):	0.951
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.96
Plasma Protein Binding (PPB):	32.249%	Volume Distribution (VD):	-0.604
Fu:	69.375% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.382	BCRP inhibitor:	0.001
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.231	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.142	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.0
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):

2.809

Half-life (T1/2):

3.772

ADMET: Toxicity

hERG Blockers:	0.17	hERG Blockers (10um):	0.578
Human Hepatotoxicity (H-HT):	0.76	Drug-induced Liver Injury (DILI):	0.214
AMES Toxicity:	0.828	Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.98	Skin Sensitization:	0.568
Carcinogencity:	0.697	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.317
Drug-induced Neurotoxicity:	0.174	Ototoxicity:	0.987
Hematotoxicity:	0.126	Drug-induced Nephrotoxicity:	0.116
Genotoxicity:	0.65	RPMI-8226 Immunitoxicity:	0.401
A549 Cytotoxicity:	0.19	Hek293 Cytotoxicity:	0.864
BCF:	0.529 ? 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:	3.474 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.44 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.134 ? 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	=	63.8	%	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 NPC471353 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	15249
0.1-0.2	28544
0.2-0.3	5260
0.3-0.4	592
0.4-0.5	73
0.5-0.6	71
0.6-0.7	41
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC179412
0.8462	Intermediate Similarity	NPC471356
0.8205	Intermediate Similarity	NPC76572
0.8205	Intermediate Similarity	NPC193382
0.7683	Intermediate Similarity	NPC471354
0.7683	Intermediate Similarity	NPC27507
0.7439	Intermediate Similarity	NPC77319
0.7439	Intermediate Similarity	NPC471351
0.7439	Intermediate Similarity	NPC471355
0.7407	Intermediate Similarity	NPC77299
0.7407	Intermediate Similarity	NPC480906
0.7349	Intermediate Similarity	NPC9499
0.7349	Intermediate Similarity	NPC471360
0.7349	Intermediate Similarity	NPC469751
0.7349	Intermediate Similarity	NPC471361
0.7349	Intermediate Similarity	NPC86159
0.7349	Intermediate Similarity	NPC469752
0.7349	Intermediate Similarity	NPC469754
0.7349	Intermediate Similarity	NPC70542
0.7273	Intermediate Similarity	NPC208193
0.716	Intermediate Similarity	NPC99620
0.6988	Remote Similarity	NPC469750
0.6897	Remote Similarity	NPC173555
0.6786	Remote Similarity	NPC5311
0.6742	Remote Similarity	NPC32177
0.6742	Remote Similarity	NPC469756
0.6742	Remote Similarity	NPC275901
0.6667	Remote Similarity	NPC480910
0.6667	Remote Similarity	NPC240070
0.6667	Remote Similarity	NPC196429
0.6667	Remote Similarity	NPC480909
0.6598	Remote Similarity	NPC117445
0.6598	Remote Similarity	NPC308262
0.6538	Remote Similarity	NPC196471
0.6522	Remote Similarity	NPC486135
0.6522	Remote Similarity	NPC486137
0.6512	Remote Similarity	NPC480914
0.6395	Remote Similarity	NPC157376
0.6395	Remote Similarity	NPC142066
0.6395	Remote Similarity	NPC603972
0.6364	Remote Similarity	NPC305574
0.6264	Remote Similarity	NPC30483
0.6264	Remote Similarity	NPC470897
0.6222	Remote Similarity	NPC480907
0.6196	Remote Similarity	NPC236973
0.618	Remote Similarity	NPC483822
0.6163	Remote Similarity	NPC99728
0.6163	Remote Similarity	NPC87250
0.6163	Remote Similarity	NPC244402
0.6163	Remote Similarity	NPC50305
0.6122	Remote Similarity	NPC486136
0.6023	Remote Similarity	NPC17896
0.6023	Remote Similarity	NPC469755
0.6023	Remote Similarity	NPC284406
0.6023	Remote Similarity	NPC197707
0.6023	Remote Similarity	NPC251866
0.6023	Remote Similarity	NPC480915
0.6022	Remote Similarity	NPC292467
0.6	Remote Similarity	NPC486143
0.6	Remote Similarity	NPC471359
0.6	Remote Similarity	NPC486142
0.6	Remote Similarity	NPC486149
0.5977	Remote Similarity	NPC471633
0.5957	Remote Similarity	NPC188234
0.5833	Remote Similarity	NPC125077
0.5806	Remote Similarity	NPC474466
0.5789	Remote Similarity	NPC471357
0.5789	Remote Similarity	NPC469757
0.5789	Remote Similarity	NPC117702
0.5773	Remote Similarity	NPC232785
0.5773	Remote Similarity	NPC486139
0.575	Remote Similarity	NPC189588
0.573	Remote Similarity	NPC84987
0.5714	Remote Similarity	NPC329986
0.5714	Remote Similarity	NPC140092
0.5714	Remote Similarity	NPC486146
0.5699	Remote Similarity	NPC72260
0.5644	Remote Similarity	NPC486144
0.5644	Remote Similarity	NPC486145
0.5644	Remote Similarity	NPC486147
0.5644	Remote Similarity	NPC475590
0.5644	Remote Similarity	NPC486148
0.5604	Remote Similarity	NPC199428
0.5604	Remote Similarity	NPC109448
0.5604	Remote Similarity	NPC310341
0.5595	Remote Similarity	NPC475030
0.5591	Remote Similarity	NPC469753
0.5579	Remote Similarity	NPC475136
0.5543	Remote Similarity	NPC83287
0.5534	Remote Similarity	NPC120390
0.5534	Remote Similarity	NPC74259
0.5534	Remote Similarity	NPC475419
0.55	Remote Similarity	NPC486138
0.55	Remote Similarity	NPC276838
0.5481	Remote Similarity	NPC474908
0.5444	Remote Similarity	NPC473852
0.5435	Remote Similarity	NPC84949
0.5435	Remote Similarity	NPC480562
0.5435	Remote Similarity	NPC74945
0.5435	Remote Similarity	NPC31354
0.5435	Remote Similarity	NPC69576
0.5408	Remote Similarity	NPC231518
0.5408	Remote Similarity	NPC488944
0.5385	Remote Similarity	NPC309034
0.5376	Remote Similarity	NPC250556
0.5361	Remote Similarity	NPC27363
0.5361	Remote Similarity	NPC40749
0.5333	Remote Similarity	NPC486134
0.5333	Remote Similarity	NPC486141
0.5327	Remote Similarity	NPC474423
0.53	Remote Similarity	NPC469749
0.5152	Remote Similarity	NPC475556
0.5152	Remote Similarity	NPC32793
0.5152	Remote Similarity	NPC116075
0.5152	Remote Similarity	NPC311706
0.5146	Remote Similarity	NPC475219
0.514	Remote Similarity	NPC486150
0.5119	Remote Similarity	NPC222875
0.5119	Remote Similarity	NPC25177
0.5106	Remote Similarity	NPC480908
0.5104	Remote Similarity	NPC193893
0.51	Remote Similarity	NPC264336
0.51	Remote Similarity	NPC488941
0.51	Remote Similarity	NPC475629
0.51	Remote Similarity	NPC488940
0.5096	Remote Similarity	NPC479360
0.5096	Remote Similarity	NPC479359
0.5096	Remote Similarity	NPC488943
0.5096	Remote Similarity	NPC488942
0.5091	Remote Similarity	NPC286809
0.5052	Remote Similarity	NPC488162
0.5052	Remote Similarity	NPC93416
0.505	Remote Similarity	NPC55532

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6197
0.1-0.2	2826
0.2-0.3	106
0.3-0.4	7
0.4-0.5	2
0.5-0.6	6
0.6-0.7	6
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
0.6897	Remote Similarity	NPD8296	Phase 4
0.6437	Remote Similarity	NPD8335	Phase 4
0.6364	Remote Similarity	NPD8380	Approved
0.6105	Remote Similarity	NPD8378	Pre-clinical
0.6105	Remote Similarity	NPD8379	Approved
0.6023	Remote Similarity	NPD7319	Approved
0.5699	Remote Similarity	NPD8294	Phase 4
0.5543	Remote Similarity	NPD7327	Approved
0.5543	Remote Similarity	NPD7328	Phase 4
0.5408	Remote Similarity	NPD8033	Approved
0.5376	Remote Similarity	NPD7507	Pre-clinical
0.505	Remote Similarity	NPD8377	Phase 4

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