NPASS Compound

Natural Product: NPC298477

Natural Product ID	NPC298477
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PIWUFWOLNMAXSJ-WAHAIZDPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	70697800
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 94 99 0 0 0 0 0 0 0 0999 V2000 5.5396 2.7559 0.0988 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8753 2.0742 0.3077 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5827 1.9708 -1.0252 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3079 0.6367 -1.0371 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2387 -0.4364 -1.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3165 -0.1661 0.1375 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7657 0.8695 0.9520 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0165 0.0173 -0.2911 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1307 -0.9488 0.1817 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0898 -0.2809 1.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8767 0.2072 0.2625 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2706 -0.8385 -0.6614 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2785 -0.2490 -2.0602 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1148 -2.0453 -0.7106 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6323 -3.2450 -0.5626 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1906 -3.5538 -0.3278 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6772 -2.3960 -0.7463 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0927 -1.1485 -0.1675 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0640 0.0147 -0.4679 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3059 -0.2674 0.3550 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9397 -1.5641 0.0544 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9306 -1.2675 -1.1132 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8181 -2.1006 1.1527 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8254 -3.5782 0.8232 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3432 -3.8064 0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0845 -2.6756 -0.4464 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6509 -3.1818 -1.6585 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4682 -1.7942 2.5210 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3248 -1.1682 3.1930 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2532 -2.0982 3.2873 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1668 -1.6929 0.9407 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2949 0.7360 0.1367 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6338 1.5895 1.1449 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0368 1.4411 2.2280 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6354 2.6456 1.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3124 2.8697 -0.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2958 3.9333 -0.1268 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6077 4.7796 0.8966 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5722 5.7613 0.7226 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2340 5.9146 -0.4592 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9293 5.0617 -1.5126 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9736 4.0980 -1.3217 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5109 -2.2959 -2.1492 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5807 -1.7892 -0.9355 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0945 0.5043 0.1046 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4843 3.0058 -1.2259 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9965 2.3502 -0.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6364 3.8471 -0.0223 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8641 2.5970 0.9891 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4892 2.7513 0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8292 1.9382 -1.8288 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8867 0.5559 -1.9736 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7268 -1.4379 -0.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6705 -0.4004 -1.9748 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3356 -1.0756 0.7759 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7632 -1.6406 0.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7151 -1.0330 1.7598 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4789 0.5568 1.6128 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2148 1.0513 -0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1375 0.5599 0.9844 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2905 0.2553 -2.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2996 -1.0141 -2.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5607 0.5654 -2.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3024 -4.0879 -0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0692 -4.4251 -0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 -3.8083 0.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0397 -1.1716 0.9412 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5583 0.8853 -0.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2728 0.0776 -1.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9703 -0.2205 1.3986 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3114 -2.2019 -1.5321 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4167 -0.6131 -1.8273 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7800 -0.7008 -0.6930 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3559 -3.6932 -0.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2070 -4.2070 1.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3016 -4.7973 0.0256 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7323 -3.7388 1.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2763 -4.1094 -1.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2952 -1.9221 2.8021 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2296 -3.1399 3.6782 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2056 -1.4708 4.2323 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6828 -2.2340 1.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8203 3.2608 1.8874 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1238 2.2514 -0.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1217 4.7046 1.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8230 6.4435 1.5480 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9922 6.6952 -0.5780 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4621 5.1889 -2.4547 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7489 3.4337 -2.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2971 -1.8533 -2.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1583 -2.7097 -1.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6681 -1.2125 -1.8771 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4489 -0.4187 0.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0918 3.0701 -0.4477 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 6 12 14 1 0 14 15 2 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 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 23 28 1 0 28 29 2 0 28 30 1 0 23 31 1 6 20 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 17 43 1 6 14 44 1 0 4 45 1 0 3 46 1 0 7 2 1 0 44 9 1 0 18 12 1 0 26 21 1 0 42 37 1 0 26 17 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 1 3 51 1 6 4 52 1 6 5 53 1 0 5 54 1 0 6 55 1 1 9 56 1 1 10 57 1 0 10 58 1 0 11 59 1 0 11 60 1 0 13 61 1 0 13 62 1 0 13 63 1 0 15 64 1 0 16 65 1 0 16 66 1 0 18 67 1 1 19 68 1 0 19 69 1 0 20 70 1 1 22 71 1 0 22 72 1 0 22 73 1 0 24 74 1 0 24 75 1 0 25 76 1 0 25 77 1 0 27 78 1 0 30 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 35 83 1 0 36 84 1 0 38 85 1 0 39 86 1 0 40 87 1 0 41 88 1 0 42 89 1 0 43 90 1 0 44 91 1 0 44 92 1 0 45 93 1 0 46 94 1 0 M END

Standard InCHIKey	PIWUFWOLNMAXSJ-WAHAIZDPSA-N
Standard InCHI	InChI=1S/C36H48O10/c1-21-31(40)26(38)19-30(44-21)45-25-13-14-32(3)24(18-25)12-15-35(42)27(32)20-28(46-29(39)11-10-23-8-6-5-7-9-23)33(4)34(41,22(2)37)16-17-36(33,35)43/h5-12,21,25-28,30-31,38,40-43H,13-20H2,1-4H3/b11-10+/t21-,25+,26+,27-,28-,30+,31-,32+,33-,34-,35+,36-/m1/s1
SMILES	C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([C@@H]2C[C@H]([C@]2(C)[C@@](CC[C@]32O)(C(=O)C)O)OC(=O)/C=C/c2ccccc2)O)C1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	640.32	Volume:	649.32 ? Van der Waals volume.
Dense:	0.986	LogP:	2.594 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.733 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.7 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	35.0
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:	0.178	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.337	Fsp³:	0.667
MCE-18:	161.333 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.907	Fluc inhibitor:	0.386 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.291 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.08	Promiscuous compounds:	0.361

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.137	MDCK Permeability:	-5.215
Pgp-inhibitor:	0.037	Pgp-substrate:	0.731
PAMPA:	0.995 ? 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%):	0.801	30% Bioavailability (F30%):	0.78
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.845
Plasma Protein Binding (PPB):	93.265%	Volume Distribution (VD):	0.249
Fu:	4.676% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.016
BSEP inhibitor:	0.932

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.001 ? 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):

3.272

Half-life (T1/2):

2.585

ADMET: Toxicity

hERG Blockers:	0.085	hERG Blockers (10um):	0.191
Human Hepatotoxicity (H-HT):	0.815	Drug-induced Liver Injury (DILI):	0.783
AMES Toxicity:	0.916	Rat Oral Acute Toxicity:	0.729
Maximum Recommended Daily Dose:	0.959	Skin Sensitization:	0.999
Carcinogencity:	0.831	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.683
Drug-induced Neurotoxicity:	0.197	Ototoxicity:	0.837
Hematotoxicity:	0.419	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.359
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.954
BCF:	0.752 ? 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:	3.616 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.309 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.675 ? 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
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[18401845]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	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

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

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 NPC298477 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	10578
0.1-0.2	33977
0.2-0.3	5024
0.3-0.4	229
0.4-0.5	12
0.5-0.6	23
0.6-0.7	11
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
0.7449	Intermediate Similarity	NPC165234
0.7449	Intermediate Similarity	NPC481659
0.7449	Intermediate Similarity	NPC271687
0.7228	Intermediate Similarity	NPC475536
0.6981	Remote Similarity	NPC473641
0.6981	Remote Similarity	NPC475300
0.6697	Remote Similarity	NPC475437
0.6697	Remote Similarity	NPC475464
0.6549	Remote Similarity	NPC473797
0.6518	Remote Similarity	NPC481648
0.6415	Remote Similarity	NPC474564
0.6389	Remote Similarity	NPC475613
0.6239	Remote Similarity	NPC481654
0.6216	Remote Similarity	NPC70236
0.6053	Remote Similarity	NPC475567
0.5984	Remote Similarity	NPC481650
0.5965	Remote Similarity	NPC476092
0.5882	Remote Similarity	NPC475175
0.5847	Remote Similarity	NPC475447
0.5769	Remote Similarity	NPC478506
0.5758	Remote Similarity	NPC481657
0.5714	Remote Similarity	NPC481660
0.5644	Remote Similarity	NPC473519
0.562	Remote Similarity	NPC475531
0.562	Remote Similarity	NPC475198
0.5619	Remote Similarity	NPC473805
0.5577	Remote Similarity	NPC481658
0.5577	Remote Similarity	NPC79250
0.5577	Remote Similarity	NPC290746
0.5469	Remote Similarity	NPC476090
0.5421	Remote Similarity	NPC481661
0.5421	Remote Similarity	NPC305378
0.5421	Remote Similarity	NPC102015
0.5421	Remote Similarity	NPC481655
0.5385	Remote Similarity	NPC607555
0.5113	Remote Similarity	NPC481647
0.5043	Remote Similarity	NPC481649
0.5042	Remote Similarity	NPC475218

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC298477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4304
0.1-0.2	4732
0.2-0.3	112
0.3-0.4	2
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