NPASS Compound

Natural Product: NPC219085

Natural Product ID	NPC219085
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Xylopyranosylstrophanthidin
IUPAC Name	(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-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	CHEMBL249081
PubChem CID	44445806
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 78 83 0 0 0 0 0 0 0 0999 V2000 0.7989 3.1543 -0.7770 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3310 2.6314 0.1918 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2801 1.1353 0.3949 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0704 0.8718 1.6581 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5400 1.0680 1.2537 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9214 -0.1806 0.4942 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8346 -0.6820 -0.3827 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 0.4043 -0.8036 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5552 1.2936 -1.5965 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1869 -0.2687 -1.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4509 0.5003 -1.8573 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8751 1.3381 -0.6913 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1551 0.7636 0.5120 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8488 1.2327 1.7359 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1679 0.4389 1.7647 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9770 0.6486 0.5403 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3244 1.5214 -0.4997 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5681 2.8515 -0.1139 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1447 1.2719 -1.7456 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9654 0.0346 -1.4741 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4109 -0.5648 -0.1962 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4354 -1.3984 0.4953 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6381 -1.7041 0.0609 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3340 -2.5368 1.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5129 -3.0221 0.9400 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4541 -2.7087 2.0677 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2569 -2.0272 1.8136 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2509 1.3871 0.9814 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1117 -0.0583 -0.1949 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1064 -0.9003 0.2768 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1048 -0.0941 0.8238 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8980 0.4705 -0.1742 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8500 -0.5753 -0.7278 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1989 -1.9251 -0.4685 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7234 -1.7620 -0.7762 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1792 -3.0430 -0.8203 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7836 -2.9459 -1.1819 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0806 -0.5324 -0.0725 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0821 3.2332 0.9748 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8939 -0.1174 2.0831 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 1.7047 2.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0959 1.2169 2.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6044 1.9102 0.5459 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1016 -0.9688 1.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2665 -1.5381 0.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2755 -1.0556 -1.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3269 1.2049 -2.5553 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2764 -0.4928 -2.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3930 -1.2723 -1.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 -0.2410 -2.1845 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2922 1.1476 -2.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3915 2.3471 -0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2538 -0.3515 0.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3078 1.0063 2.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1427 2.2961 1.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8427 -0.6149 1.8830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7179 0.6957 2.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2222 3.2985 -0.6887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5495 1.2197 -2.6662 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8830 2.1076 -1.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0489 0.3026 -1.2936 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9552 -0.6589 -2.3215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5521 -1.1887 -0.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0732 -1.3846 -0.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4635 -2.8317 1.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0095 -1.2931 2.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9294 0.7162 1.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8909 2.1434 1.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7154 1.9359 0.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7191 -1.5159 1.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4547 1.3430 0.2164 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2741 0.8589 -1.0137 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9634 -0.4744 -1.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2703 -2.0864 0.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5834 -1.2767 -1.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4990 -3.5999 -0.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4407 -3.3877 -0.5557 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7869 -0.4263 -0.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 3 2 1 6 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 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 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 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 16 28 1 1 6 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 13 3 1 0 21 16 1 0 27 22 1 0 35 30 1 0 8 3 1 0 17 12 1 0 2 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 1 7 45 1 0 7 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 12 52 1 6 13 53 1 6 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 6 23 64 1 0 27 65 1 0 27 66 1 0 28 67 1 0 28 68 1 0 28 69 1 0 30 70 1 1 32 71 1 0 32 72 1 0 33 73 1 6 34 74 1 1 35 75 1 6 36 76 1 0 37 77 1 0 38 78 1 0 M END

Standard InCHIKey	XMNREHIXCIWCGI-OIAVFDJJSA-N
Standard InCHI	InChI=1S/C28H40O10/c1-25-6-3-18-19(28(25,35)9-5-17(25)15-10-21(31)36-12-15)4-8-27(34)11-16(2-7-26(18,27)14-29)38-24-23(33)22(32)20(30)13-37-24/h10,14,16-20,22-24,30,32-35H,2-9,11-13H2,1H3/t16-,17+,18-,19+,20+,22-,23+,24-,25+,26-,27-,28-/m0/s1
SMILES	O=C[C@@]12CC[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1CC[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.26	Volume:	521.498 ? Van der Waals volume.
Dense:	1.028	LogP:	0.351 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.114 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.662 ? 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:	0.193	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.291	Fsp³:	0.857
MCE-18:	115.385 ? 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:	0.757	Fluc inhibitor:	0.007 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.137	Promiscuous compounds:	0.281

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.908	MDCK Permeability:	-5.18
Pgp-inhibitor:	0.0	Pgp-substrate:	0.982
PAMPA:	0.999 ? 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):	0.002
20% Bioavailability (F20%):	0.408	30% Bioavailability (F30%):	0.378
50% Bioavailability (F50%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061	MRP1:	0.695
Plasma Protein Binding (PPB):	57.616%	Volume Distribution (VD):	-0.441
Fu:	43.021% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.002
BSEP inhibitor:	0.44

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.08	CYP3A4-substrate:	0.02
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.53
HLM stability:	0.002 ? 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):

1.888

Half-life (T1/2):

3.565

ADMET: Toxicity

hERG Blockers:	0.037	hERG Blockers (10um):	0.212
Human Hepatotoxicity (H-HT):	0.813	Drug-induced Liver Injury (DILI):	0.172
AMES Toxicity:	0.882	Rat Oral Acute Toxicity:	0.563
Maximum Recommended Daily Dose:	0.977	Skin Sensitization:	1.0
Carcinogencity:	0.923	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.384
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.857
Hematotoxicity:	0.454	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.972	RPMI-8226 Immunitoxicity:	0.413
A549 Cytotoxicity:	0.697	Hek293 Cytotoxicity:	0.842
BCF:	0.5 ? 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:	3.263 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.944 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.056 ? 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
NPO587	Saussurea stella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17844995]
NPO587	Saussurea stella	Species	Asteraceae	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	2

Activity Type	# Activity
Cell line	1
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
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	130.0	nM	PMID[18076141]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	16.0	nM	PMID[17844995]

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 NPC219085 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	15557
0.1-0.2	29290
0.2-0.3	4586
0.3-0.4	218
0.4-0.5	87
0.5-0.6	67
0.6-0.7	26
0.7-0.8	0
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC158344
0.8481	Intermediate Similarity	NPC608063
0.8267	Intermediate Similarity	NPC17896
0.8267	Intermediate Similarity	NPC469755
0.8267	Intermediate Similarity	NPC284406
0.8267	Intermediate Similarity	NPC197707
0.8267	Intermediate Similarity	NPC251866
0.7381	Intermediate Similarity	NPC32793
0.7381	Intermediate Similarity	NPC116075
0.7126	Intermediate Similarity	NPC469749
0.7125	Intermediate Similarity	NPC6108
0.7125	Intermediate Similarity	NPC157376
0.7125	Intermediate Similarity	NPC89514
0.7125	Intermediate Similarity	NPC142066
0.7125	Intermediate Similarity	NPC603972
0.7089	Intermediate Similarity	NPC99728
0.7089	Intermediate Similarity	NPC87250
0.7089	Intermediate Similarity	NPC244402
0.7089	Intermediate Similarity	NPC50305
0.7037	Intermediate Similarity	NPC10823
0.7	Intermediate Similarity	NPC84987
0.6951	Remote Similarity	NPC180079
0.6854	Remote Similarity	NPC146857
0.6854	Remote Similarity	NPC247190
0.6667	Remote Similarity	NPC9499
0.6667	Remote Similarity	NPC471360
0.6667	Remote Similarity	NPC469751
0.6667	Remote Similarity	NPC471361
0.6667	Remote Similarity	NPC86159
0.6667	Remote Similarity	NPC469752
0.6667	Remote Similarity	NPC469754
0.6667	Remote Similarity	NPC70542
0.6627	Remote Similarity	NPC604978
0.6526	Remote Similarity	NPC194716
0.64	Remote Similarity	NPC72772
0.6354	Remote Similarity	NPC329675
0.631	Remote Similarity	NPC469750
0.6279	Remote Similarity	NPC471359
0.6264	Remote Similarity	NPC59288
0.6235	Remote Similarity	NPC480914
0.619	Remote Similarity	NPC309034
0.6154	Remote Similarity	NPC475629
0.6145	Remote Similarity	NPC474418
0.6071	Remote Similarity	NPC99620
0.6044	Remote Similarity	NPC475556
0.6044	Remote Similarity	NPC311706
0.6042	Remote Similarity	NPC329636
0.5977	Remote Similarity	NPC77319
0.5977	Remote Similarity	NPC471351
0.5977	Remote Similarity	NPC471355
0.593	Remote Similarity	NPC5311
0.593	Remote Similarity	NPC77299
0.593	Remote Similarity	NPC34390
0.593	Remote Similarity	NPC480906
0.5862	Remote Similarity	NPC76572
0.5862	Remote Similarity	NPC193382
0.5843	Remote Similarity	NPC471354
0.5843	Remote Similarity	NPC27507
0.5699	Remote Similarity	NPC188234
0.5682	Remote Similarity	NPC243196
0.5667	Remote Similarity	NPC469753
0.5652	Remote Similarity	NPC30483
0.5652	Remote Similarity	NPC470897
0.5641	Remote Similarity	NPC10232
0.5618	Remote Similarity	NPC250556
0.5604	Remote Similarity	NPC480907
0.5584	Remote Similarity	NPC97487
0.5568	Remote Similarity	NPC480915
0.5521	Remote Similarity	NPC232785
0.5521	Remote Similarity	NPC486139
0.5474	Remote Similarity	NPC264336
0.5455	Remote Similarity	NPC196429
0.5455	Remote Similarity	NPC484211
0.5444	Remote Similarity	NPC146456
0.5426	Remote Similarity	NPC236973
0.5426	Remote Similarity	NPC32177
0.5426	Remote Similarity	NPC469756
0.5426	Remote Similarity	NPC275901
0.5417	Remote Similarity	NPC125077
0.5408	Remote Similarity	NPC486138
0.5408	Remote Similarity	NPC276838
0.5368	Remote Similarity	NPC480910
0.5368	Remote Similarity	NPC240070
0.5368	Remote Similarity	NPC480909
0.5333	Remote Similarity	NPC199428
0.5333	Remote Similarity	NPC109448
0.5333	Remote Similarity	NPC310341
0.5312	Remote Similarity	NPC610296
0.5306	Remote Similarity	NPC329986
0.5306	Remote Similarity	NPC140092
0.5275	Remote Similarity	NPC88668
0.5275	Remote Similarity	NPC484212
0.5275	Remote Similarity	NPC83287
0.5263	Remote Similarity	NPC292467
0.5258	Remote Similarity	NPC486143
0.5258	Remote Similarity	NPC486135
0.5258	Remote Similarity	NPC486142
0.5258	Remote Similarity	NPC486137
0.5258	Remote Similarity	NPC486149
0.5217	Remote Similarity	NPC179412
0.5217	Remote Similarity	NPC93883
0.5217	Remote Similarity	NPC471356
0.5217	Remote Similarity	NPC305574
0.5192	Remote Similarity	NPC486150
0.5169	Remote Similarity	NPC471633
0.5152	Remote Similarity	NPC486146
0.5098	Remote Similarity	NPC486144
0.5098	Remote Similarity	NPC486145
0.5098	Remote Similarity	NPC486147
0.5098	Remote Similarity	NPC486136
0.5098	Remote Similarity	NPC486148
0.5062	Remote Similarity	NPC196931
0.5055	Remote Similarity	NPC486126
0.5054	Remote Similarity	NPC484202

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC219085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6061
0.1-0.2	2938
0.2-0.3	136
0.3-0.4	4
0.4-0.5	7
0.5-0.6	3
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8267	Intermediate Similarity	NPD7319	Approved
0.5618	Remote Similarity	NPD7507	Pre-clinical
0.5275	Remote Similarity	NPD7327	Approved
0.5275	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