NPASS Compound

Natural Product: NPC509605

Natural Product ID	NPC509605
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Adonitoxol (Adonitoxilogenin-Rha)
IUPAC Name	3-[(3~{S},5~{R},8~{R},9~{S},10~{R},13~{R},14~{S},16~{S},17~{R})-14,16-dihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2~{H}-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 7.7950 -0.1201 2.0467 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4887 0.1059 1.2732 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8746 -1.1161 1.1718 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9673 -1.2067 0.1110 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0628 -0.1692 0.0911 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7277 -0.5998 0.2006 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1698 0.0170 1.4362 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6680 0.0872 1.4733 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0988 0.7147 0.2068 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7900 2.0484 0.0675 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3774 2.7328 -1.0614 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5158 -0.1493 -0.9341 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0272 -1.5667 -0.7365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4018 -1.6604 -0.2898 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0504 -0.3245 -0.4110 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3720 0.7659 0.3720 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0116 2.0757 0.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4812 2.0512 0.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2226 0.8816 -0.2791 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4007 1.2147 -1.7435 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5101 0.6439 0.4730 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4957 -0.1626 -0.2548 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8242 -1.4002 0.0702 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8332 -1.8965 -0.8622 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3672 -3.0607 -0.8306 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0724 -0.8800 -1.7436 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3144 0.2469 -1.3921 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9638 -0.0412 1.7129 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9026 -0.6310 2.5111 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8355 -0.9317 1.2575 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5165 -0.4360 -0.1133 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0516 -1.2847 -1.1130 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0261 -0.2275 -1.0573 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7510 -1.1672 -1.1847 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0001 -2.4584 -1.6650 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0325 -0.3715 -1.0537 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1027 -1.1596 -0.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8301 0.7223 -0.0433 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8967 1.6638 -0.4407 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1376 -1.1725 1.8546 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5742 0.5458 1.6758 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6224 0.0505 3.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8407 0.7606 1.9061 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4918 -2.2040 0.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7940 -1.7246 0.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4687 -0.6487 2.2981 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6386 0.9972 1.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3928 0.7771 2.3013 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2117 -0.8922 1.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8765 1.8511 -0.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7038 2.6629 0.9908 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1015 3.2687 -1.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1785 0.2592 -1.9294 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2447 -2.1726 -1.6412 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6596 -2.0139 0.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5455 -2.1454 0.6972 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9145 -2.3347 -1.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9874 -0.0252 -1.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6691 0.5778 1.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5692 2.8541 0.6997 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8747 2.4246 -0.9945 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6229 2.2175 1.3819 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9029 2.9735 -0.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 1.6536 -2.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4947 0.3449 -2.3983 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0890 2.0449 -1.8865 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9908 1.6114 0.7795 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4584 -2.0131 0.8634 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0503 1.0537 -1.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7699 0.5300 -2.3159 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5030 0.7662 2.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2274 -0.0427 3.2468 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9873 -0.8560 1.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1382 -1.9964 1.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4552 -1.3360 -1.9014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1833 -1.0493 -1.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4435 0.6716 -1.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1589 -0.6520 -1.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2792 -2.3566 -2.6155 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2811 0.1369 -2.0263 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2721 -1.8331 -1.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8010 1.2570 0.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7068 2.2279 0.3723 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 7 8 1 0 8 9 1 0 9 10 1 6 10 11 1 0 9 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 21 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 6 12 33 1 0 4 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 38 2 1 0 33 6 1 0 16 9 1 0 31 19 1 0 31 15 1 0 27 22 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 1 4 44 1 1 6 45 1 1 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 11 52 1 0 12 53 1 6 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 6 16 59 1 1 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 21 67 1 1 23 68 1 0 27 69 1 0 27 70 1 0 28 71 1 1 29 72 1 0 30 73 1 0 30 74 1 0 32 75 1 0 33 76 1 0 33 77 1 0 34 78 1 6 35 79 1 0 36 80 1 6 37 81 1 0 38 82 1 1 39 83 1 0 M END

Standard InCHIKey	WREOBZCLAMYMIG-BBNLJEPRSA-N
Standard InCHI	InChI=1S/C29H44O10/c1-14-23(33)24(34)25(35)26(38-14)39-17-5-8-28(13-30)16(10-17)3-4-19-18(28)6-7-27(2)22(15-9-21(32)37-12-15)20(31)11-29(19,27)36/h9,14,16-20,22-26,30-31,33-36H,3-8,10-13H2,1-2H3/t14-,16+,17-,18-,19+,20-,22-,23-,24+,25+,26-,27+,28+,29-/m0/s1
SMILES	C[C@@H]1O[C@@H](O[C@H]2CC[C@@]3(CO)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H](C5=CC(=O)OC5)[C@@H](O)C[C@]43O)C2)[C@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.29	Volume:	541.431 ? Van der Waals volume.
Dense:	1.02	LogP:	0.522 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.115 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.34 ? 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:	5.357	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:	0.68	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? 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:	0.128	Promiscuous compounds:	0.278

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.181	MDCK Permeability:	-5.157
Pgp-inhibitor:	0.0	Pgp-substrate:	0.916
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):	0.345
20% Bioavailability (F20%):	0.287	30% Bioavailability (F30%):	0.857
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165	MRP1:	0.184
Plasma Protein Binding (PPB):	73.987%	Volume Distribution (VD):	-0.393
Fu:	25.296% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.045
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.019	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:	0.889	CYP3A4-substrate:	0.848
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.094
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):

1.313

Half-life (T1/2):

4.28

ADMET: Toxicity

hERG Blockers:	0.057	hERG Blockers (10um):	0.556
Human Hepatotoxicity (H-HT):	0.347	Drug-induced Liver Injury (DILI):	0.698
AMES Toxicity:	0.85	Rat Oral Acute Toxicity:	0.758
Maximum Recommended Daily Dose:	0.971	Skin Sensitization:	1.0
Carcinogencity:	0.445	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.907
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.858
Hematotoxicity:	0.785	Drug-induced Nephrotoxicity:	0.969
Genotoxicity:	0.948	RPMI-8226 Immunitoxicity:	0.607
A549 Cytotoxicity:	0.124	Hek293 Cytotoxicity:	0.614
BCF:	0.55 ? 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:	3.13 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.453 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.593 ? 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
NPO50497	Adonis vernalis L.	Genus	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC509605 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	14843
0.1-0.2	29205
0.2-0.3	5020
0.3-0.4	589
0.4-0.5	77
0.5-0.6	77
0.6-0.7	34
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8289	Intermediate Similarity	NPC76572
0.8289	Intermediate Similarity	NPC193382
0.7468	Intermediate Similarity	NPC77299
0.7468	Intermediate Similarity	NPC480906
0.7407	Intermediate Similarity	NPC471353
0.7011	Intermediate Similarity	NPC231518
0.7011	Intermediate Similarity	NPC488944
0.7	Intermediate Similarity	NPC99620
0.6829	Remote Similarity	NPC469750
0.6782	Remote Similarity	NPC32177
0.6782	Remote Similarity	NPC469756
0.6782	Remote Similarity	NPC275901
0.6705	Remote Similarity	NPC480910
0.6705	Remote Similarity	NPC480909
0.6627	Remote Similarity	NPC5311
0.6627	Remote Similarity	NPC479356
0.6627	Remote Similarity	NPC479355
0.6559	Remote Similarity	NPC479360
0.6559	Remote Similarity	NPC479359
0.6556	Remote Similarity	NPC486135
0.6556	Remote Similarity	NPC486137
0.6517	Remote Similarity	NPC240070
0.6512	Remote Similarity	NPC193893
0.6395	Remote Similarity	NPC305574
0.6353	Remote Similarity	NPC480914
0.631	Remote Similarity	NPC196429
0.6235	Remote Similarity	NPC157376
0.6235	Remote Similarity	NPC99080
0.6235	Remote Similarity	NPC142066
0.6235	Remote Similarity	NPC603972
0.6207	Remote Similarity	NPC179412
0.6207	Remote Similarity	NPC471356
0.6146	Remote Similarity	NPC486136
0.6111	Remote Similarity	NPC30483
0.6111	Remote Similarity	NPC470897
0.6067	Remote Similarity	NPC480907
0.6044	Remote Similarity	NPC236973
0.6023	Remote Similarity	NPC483822
0.6	Remote Similarity	NPC99728
0.6	Remote Similarity	NPC87250
0.6	Remote Similarity	NPC244402
0.6	Remote Similarity	NPC50305
0.587	Remote Similarity	NPC292467
0.5862	Remote Similarity	NPC17896
0.5862	Remote Similarity	NPC469755
0.5862	Remote Similarity	NPC284406
0.5862	Remote Similarity	NPC197707
0.5862	Remote Similarity	NPC251866
0.5862	Remote Similarity	NPC480915
0.5851	Remote Similarity	NPC486143
0.5851	Remote Similarity	NPC486142
0.5851	Remote Similarity	NPC486149
0.5806	Remote Similarity	NPC188234
0.5632	Remote Similarity	NPC471633
0.5625	Remote Similarity	NPC232785
0.5625	Remote Similarity	NPC486139
0.5604	Remote Similarity	NPC471354
0.5604	Remote Similarity	NPC27507
0.5568	Remote Similarity	NPC84987
0.5567	Remote Similarity	NPC486146
0.5556	Remote Similarity	NPC77319
0.5556	Remote Similarity	NPC471351
0.5556	Remote Similarity	NPC488943
0.5556	Remote Similarity	NPC471355
0.5556	Remote Similarity	NPC488942
0.5521	Remote Similarity	NPC125077
0.55	Remote Similarity	NPC486144
0.55	Remote Similarity	NPC486145
0.55	Remote Similarity	NPC486147
0.55	Remote Similarity	NPC486148
0.5455	Remote Similarity	NPC475219
0.5444	Remote Similarity	NPC199428
0.5444	Remote Similarity	NPC109448
0.5444	Remote Similarity	NPC310341
0.5408	Remote Similarity	NPC329986
0.5408	Remote Similarity	NPC140092
0.54	Remote Similarity	NPC488938
0.54	Remote Similarity	NPC488937
0.5376	Remote Similarity	NPC72260
0.5368	Remote Similarity	NPC40749
0.5361	Remote Similarity	NPC208193
0.5354	Remote Similarity	NPC486138
0.5354	Remote Similarity	NPC276838
0.5347	Remote Similarity	NPC475590
0.5326	Remote Similarity	NPC9499
0.5326	Remote Similarity	NPC471360
0.5326	Remote Similarity	NPC469751
0.5326	Remote Similarity	NPC471361
0.5326	Remote Similarity	NPC86159
0.5326	Remote Similarity	NPC469752
0.5326	Remote Similarity	NPC469754
0.5326	Remote Similarity	NPC70542
0.5316	Remote Similarity	NPC220217
0.5258	Remote Similarity	NPC488941
0.5258	Remote Similarity	NPC488940
0.5243	Remote Similarity	NPC120390
0.5243	Remote Similarity	NPC74259
0.5243	Remote Similarity	NPC475419
0.5238	Remote Similarity	NPC488945
0.5238	Remote Similarity	NPC488946
0.5222	Remote Similarity	NPC309034
0.5217	Remote Similarity	NPC250556
0.5208	Remote Similarity	NPC27363
0.5192	Remote Similarity	NPC474908
0.5192	Remote Similarity	NPC486134
0.5192	Remote Similarity	NPC486141
0.5158	Remote Similarity	NPC5883
0.5152	Remote Similarity	NPC469749
0.5122	Remote Similarity	NPC222875
0.5122	Remote Similarity	NPC25177
0.5109	Remote Similarity	NPC84949
0.5109	Remote Similarity	NPC480562
0.5109	Remote Similarity	NPC74945
0.5109	Remote Similarity	NPC31354
0.5109	Remote Similarity	NPC24839
0.5109	Remote Similarity	NPC69576
0.5054	Remote Similarity	NPC83287
0.5047	Remote Similarity	NPC474423
0.5047	Remote Similarity	NPC488947

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC509605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6065
0.1-0.2	2941
0.2-0.3	123
0.3-0.4	7
0.4-0.5	7
0.5-0.6	5
0.6-0.7	0
0.7-0.8	1
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
0.7011	Intermediate Similarity	NPD8033	Approved
0.5862	Remote Similarity	NPD7319	Approved
0.5376	Remote Similarity	NPD8294	Phase 4
0.5217	Remote Similarity	NPD7507	Pre-clinical
0.5054	Remote Similarity	NPD7327	Approved
0.5054	Remote Similarity	NPD7328	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