NPASS Compound

Natural Product: NPC470094

Natural Product ID	NPC470094
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JHKLDCGHXADNGS-DJHKYUSNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL175806
PubChem CID	44387914
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 84 91 0 0 0 0 0 0 0 0999 V2000 0.7371 -2.0941 1.2600 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1214 -1.0793 1.6060 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0127 0.1132 0.7308 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9686 -0.0613 -0.4179 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3561 -0.0016 0.1180 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3203 -0.3350 -0.8420 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5266 -0.3547 -0.1384 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3934 -1.0171 1.0843 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8561 1.0906 0.1743 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9217 1.6089 1.0261 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6156 1.3599 0.7117 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7365 1.4062 1.9844 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3121 1.3448 1.5681 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 1.4035 2.7258 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0816 1.4287 2.2729 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3508 0.2277 1.3547 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4008 0.3439 0.2325 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7655 -0.4725 -0.9738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0386 0.1985 -1.4481 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1210 -0.1306 -0.4499 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7970 0.1369 0.9773 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3109 -0.9869 1.6870 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6453 1.2876 1.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2504 1.8937 0.1686 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2928 0.7613 -0.8353 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5996 0.0750 -0.8417 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3528 -0.0413 -1.9209 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5587 -0.7579 -1.6026 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4882 -1.0361 -2.4164 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5178 -1.0800 -0.2746 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3077 -0.5668 0.2775 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5508 -1.5592 -0.7149 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8997 1.7509 -1.0624 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0635 1.4388 -1.7405 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6466 0.1183 -1.4045 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6524 -0.9135 -0.9700 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9053 -1.7897 -2.3733 S 0 0 0 0 0 0 0 0 0 0 0 0 5.3650 -3.4982 -1.8769 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4759 -3.1602 -0.9192 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4949 -3.9372 -0.8261 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2480 -1.9887 -0.2139 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9102 1.5823 -3.2479 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3136 -1.1710 2.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7977 0.7990 -1.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7167 -1.0262 -0.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4897 -0.7481 0.9234 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3519 -0.3770 1.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8480 1.1493 0.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2333 2.1669 0.0647 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0558 0.5478 2.6034 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9146 2.3866 2.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1276 2.2114 0.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4559 0.6514 3.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4647 2.4041 3.2264 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1771 2.3892 1.7238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6833 1.3668 3.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0573 -0.6489 1.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4179 1.4200 -0.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8810 -1.5365 -0.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9988 -0.2912 -1.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3683 -0.1601 -2.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8624 1.3004 -1.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5819 -1.6249 1.8823 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5267 0.9873 2.0507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1550 2.0813 1.9627 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2506 2.2946 0.3486 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5904 2.7145 -0.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1113 1.2820 -1.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0904 0.3560 -2.9221 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5529 0.1523 1.0936 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8129 -1.4219 0.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5167 -1.6182 -1.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6209 -2.1712 0.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7677 -2.0350 -1.3655 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8153 2.2272 -1.4450 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1909 -0.2651 -2.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4188 0.2189 -0.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7233 -4.0730 -2.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5187 -3.9800 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2580 -3.7004 -0.1646 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4790 -1.8419 0.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5344 2.5865 -3.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3435 0.7658 -3.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9545 1.5228 -3.6601 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 1 7 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 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 1 21 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 20 32 1 1 9 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 6 37 38 1 0 38 39 1 0 39 40 2 3 39 41 1 0 34 42 1 0 13 3 1 0 21 16 1 0 31 26 1 0 41 36 1 0 17 3 1 0 25 20 1 0 11 5 1 0 36 7 1 0 2 43 1 0 4 44 1 0 4 45 1 0 5 46 1 1 8 47 1 0 9 48 1 1 11 49 1 6 12 50 1 0 12 51 1 0 13 52 1 6 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 1 17 58 1 6 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 25 68 1 6 27 69 1 0 31 70 1 0 31 71 1 0 32 72 1 0 32 73 1 0 32 74 1 0 34 75 1 1 35 76 1 0 35 77 1 0 38 78 1 0 38 79 1 0 40 80 1 0 41 81 1 0 42 82 1 0 42 83 1 0 42 84 1 0 M END

Standard InCHIKey	JHKLDCGHXADNGS-DJHKYUSNSA-N
Standard InCHI	InChI=1S/C31H42N2O8S/c1-16-11-30(33-24(32)14-42-30)31(37)26(39-16)40-22-10-18-3-4-21-20(28(18,15-34)12-23(22)41-31)5-7-27(2)19(6-8-29(21,27)36)17-9-25(35)38-13-17/h9,15-16,18-23,26,36-37H,3-8,10-14H2,1-2H3,(H2,32,33)/t16-,18+,19-,20+,21-,22-,23-,26+,27-,28-,29+,30+,31-/m1/s1
SMILES	O=C[C@]12C[C@H]3O[C@]4(O)[C@H](O[C@@H]3C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)O[C@@H](C[C@@]14SCC(=N)N1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.27	Volume:	576.559 ? Van der Waals volume.
Dense:	1.045	LogP:	1.405 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.88 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.301 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	43.0
TPSA:	147.4 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	8.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.211	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.547	Fsp³:	0.839
MCE-18:	192.105 ? 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:	0.783	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.011	Promiscuous compounds:	0.256

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.979	MDCK Permeability:	-5.119
Pgp-inhibitor:	0.017	Pgp-substrate:	0.979
PAMPA:	0.943 ? 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):	0.018
20% Bioavailability (F20%):	0.684	30% Bioavailability (F30%):	0.846
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.347
Plasma Protein Binding (PPB):	74.876%	Volume Distribution (VD):	0.292
Fu:	27.137% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.078
BSEP inhibitor:	0.903

ADMET: Metabolism

CYP1A2-inhibitor:	0.493	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.525	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.093	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.991	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.027
HLM stability:	0.478 ? 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):

3.823

Half-life (T1/2):

2.69

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.378
Human Hepatotoxicity (H-HT):	0.916	Drug-induced Liver Injury (DILI):	0.915
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.986	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.994
Drug-induced Neurotoxicity:	0.102	Ototoxicity:	0.725
Hematotoxicity:	0.945	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.915
A549 Cytotoxicity:	0.844	Hek293 Cytotoxicity:	0.998
BCF:	0.578 ? 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:	3.529 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.269 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.486 ? 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
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27807	Calotropis procera	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

Activity Type	# Activity
IC50	7
MTD	1

Activity Type	# Activity
Individual protein	2
Cell line	4
Organism	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6247	Individual protein	Sodium/potassium-transporting ATPase alpha-1 chain	Sus scrofa	IC50	=	68.0	nM	PMID[22209731]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT933	Cell line	U373 MG	Homo sapiens	IC50	=	40.0	nM	PMID[22209731]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	28.0	nM	PMID[17500572]
NPT114	Cell line	LoVo	Homo sapiens	IC50	=	10.0	nM	PMID[17500572]
NPT81	Cell line	A549	Homo sapiens	IC50	=	25.0	nM	PMID[17500572]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	4.0	nM	PMID[15689169]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	5.0	mg kg-1	PMID[15689169]

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 NPC470094 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	17611
0.1-0.2	31366
0.2-0.3	655
0.3-0.4	110
0.4-0.5	82
0.5-0.6	21
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
0.7159	Intermediate Similarity	NPC253456
0.7159	Intermediate Similarity	NPC159338
0.6966	Remote Similarity	NPC171619
0.6889	Remote Similarity	NPC277374
0.6739	Remote Similarity	NPC91
0.6596	Remote Similarity	NPC163365
0.6559	Remote Similarity	NPC488161
0.6559	Remote Similarity	NPC16569
0.6429	Remote Similarity	NPC473040
0.6327	Remote Similarity	NPC480905
0.6327	Remote Similarity	NPC85369
0.6078	Remote Similarity	NPC476221
0.6078	Remote Similarity	NPC477709
0.5957	Remote Similarity	NPC104585
0.5938	Remote Similarity	NPC42670
0.5938	Remote Similarity	NPC19124
0.5876	Remote Similarity	NPC488162
0.5876	Remote Similarity	NPC93416
0.5657	Remote Similarity	NPC157817
0.5556	Remote Similarity	NPC298783
0.5556	Remote Similarity	NPC329905
0.5446	Remote Similarity	NPC33934
0.5392	Remote Similarity	NPC142756
0.5294	Remote Similarity	NPC488158
0.5294	Remote Similarity	NPC488159
0.5253	Remote Similarity	NPC88668
0.5227	Remote Similarity	NPC196931
0.52	Remote Similarity	NPC488160
0.5192	Remote Similarity	NPC225385
0.51	Remote Similarity	NPC250556
0.5098	Remote Similarity	NPC609258
0.5051	Remote Similarity	NPC469750
0.5051	Remote Similarity	NPC480915
0.5049	Remote Similarity	NPC474466

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6732
0.1-0.2	2392
0.2-0.3	12
0.3-0.4	9
0.4-0.5	3
0.5-0.6	2
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
0.5333	Remote Similarity	NPD7625	Phase 1
0.51	Remote Similarity	NPD7507	Pre-clinical

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