NPASS Compound

Natural Product: NPC173923

Natural Product ID	NPC173923
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GQQJGWLFWUBFAV-CWSUONMZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101362570
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 -0.3685 3.4264 -2.5951 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0512 3.1805 -1.2875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9956 4.0843 -0.4193 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7214 2.0261 -1.0105 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3796 1.7463 0.2123 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8510 1.7658 -0.1540 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7262 0.9465 0.6683 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8149 1.4733 1.0851 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6052 -0.3822 1.1202 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7977 -1.3797 0.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6126 -1.8554 -0.7014 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6293 -2.5878 1.3642 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5729 -0.7192 -0.0189 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6375 -1.6267 -0.7380 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3485 -1.9927 -0.0980 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2189 -0.9484 0.8193 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0780 -1.4986 2.2321 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4601 0.3555 0.5629 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2719 1.4014 1.3286 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5631 1.7070 0.6000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2405 0.4407 0.0719 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3071 0.4169 -1.4098 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6924 0.5531 0.5038 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3640 1.7414 -0.0556 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5978 2.9012 0.6982 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2525 3.7558 -0.1629 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3950 3.1621 -1.3166 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8886 1.9692 -1.3096 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4311 -0.5927 0.0318 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9085 -1.8692 0.3011 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4996 -2.9376 0.0538 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5619 -1.9151 0.9211 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6964 -0.7896 0.7265 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4293 -1.0623 2.0266 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9625 0.3774 0.7837 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2992 0.4794 2.2196 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5958 -2.2714 -1.1147 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1350 -3.4905 -1.3987 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7739 -4.4747 -0.7046 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1085 -3.6223 -2.4904 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0918 3.7988 -3.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1859 2.5187 -2.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4205 4.2161 -2.4850 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1996 2.5769 0.8964 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1824 2.8322 -0.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0128 1.5937 -1.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3109 -2.8945 -0.9569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3864 -1.2359 -1.5836 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6841 -1.8269 -0.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7380 -2.3066 2.4328 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5004 -3.3053 1.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7607 -3.2078 1.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0380 -0.1481 -0.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2087 -2.5843 -0.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4003 -1.3025 -1.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4838 -3.0017 0.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9285 -2.1870 2.2428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7990 -2.1880 2.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0248 -0.7519 3.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3648 0.5850 -0.5120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5987 1.0437 2.3463 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2731 2.3203 1.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4691 2.3773 -0.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1932 2.2396 1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4087 0.1516 -1.9754 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 1.4682 -1.7325 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1071 -0.2330 -1.8158 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7402 0.5549 1.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3294 3.0830 1.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5692 4.7456 0.1349 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8785 1.2579 -2.1569 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1543 -2.9188 1.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4550 1.0911 2.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3831 -0.3980 2.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1851 1.1234 2.4655 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5806 -4.6366 -2.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9424 -2.9026 -2.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6587 -3.4427 -3.5024 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 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 2 0 26 27 1 0 27 28 1 0 23 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 33 34 1 1 18 35 1 0 35 36 1 1 15 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 35 5 1 0 35 13 1 0 33 16 1 0 33 21 1 0 28 24 2 0 34 32 1 0 1 41 1 0 1 42 1 0 1 43 1 0 5 44 1 1 6 45 1 0 6 46 1 0 11 47 1 0 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 13 53 1 6 14 54 1 0 14 55 1 0 15 56 1 1 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 6 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 1 25 69 1 0 26 70 1 0 28 71 1 0 32 72 1 1 36 73 1 0 36 74 1 0 36 75 1 0 40 76 1 0 40 77 1 0 40 78 1 0 M END

Standard InCHIKey	GQQJGWLFWUBFAV-CWSUONMZSA-N
Standard InCHI	InChI=1S/C30H38O10/c1-15(31)36-20-13-22(33)39-26(3,4)19-12-21(37-16(2)32)29(7)18(28(19,20)6)8-10-27(5)23(17-9-11-35-14-17)38-25(34)24-30(27,29)40-24/h9,11,14,18-21,23-24H,8,10,12-13H2,1-7H3/t18-,19+,20+,21-,23+,24-,27+,28-,29+,30-/m1/s1
SMILES	CC(=O)O[C@H]1CC(=O)OC(C)(C)[C@@H]2C[C@H]([C@]3(C)[C@H](CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@@H]5[C@]34O5)[C@@]12C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	558.25	Volume:	548.181 ? Van der Waals volume.
Dense:	1.018	LogP:	1.465 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.809 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.445 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	130.87 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.304	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.734	Fsp³:	0.733
MCE-18:	201.385 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.465	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.175	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.248	MDCK Permeability:	-4.971
Pgp-inhibitor:	0.998	Pgp-substrate:	0.061
PAMPA:	0.34 ? 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):	0.001
20% Bioavailability (F20%):	0.079	30% Bioavailability (F30%):	0.65
50% Bioavailability (F50%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.994
Plasma Protein Binding (PPB):	71.491%	Volume Distribution (VD):	-0.377
Fu:	29.586% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.252
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.993	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.382	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.322
HLM stability:	0.548 ? 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):

5.14

Half-life (T1/2):

0.762

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.153
Human Hepatotoxicity (H-HT):	0.455	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.469	Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.942	Skin Sensitization:	0.971
Carcinogencity:	0.696	Eye Corrosion:	0.013
Eye Irritation:	0.723	Respiratory Toxicity:	0.71
Drug-induced Neurotoxicity:	0.11	Ototoxicity:	0.572
Hematotoxicity:	0.319	Drug-induced Nephrotoxicity:	0.916
Genotoxicity:	0.989	RPMI-8226 Immunitoxicity:	0.15
A549 Cytotoxicity:	0.04	Hek293 Cytotoxicity:	0.021
BCF:	0.641 ? 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:	3.569 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.556 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.06 ? 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
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11473427]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18198838]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29135252]
NPO1329	Esenbeckia hartmanii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5451	Ageratina saltillensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7966	Grewia villosa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11119	Salta triflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5799	Streptomyces chryseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3560	Trifolium montanum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7966	Grewia villosa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11119	Salta triflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5451	Ageratina saltillensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1329	Esenbeckia hartmanii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5799	Streptomyces chryseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3560	Trifolium montanum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	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 NPC173923 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	13086
0.1-0.2	34632
0.2-0.3	1897
0.3-0.4	180
0.4-0.5	23
0.5-0.6	22
0.6-0.7	13
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
0.7895	Intermediate Similarity	NPC237155
0.7532	Intermediate Similarity	NPC611370
0.7215	Intermediate Similarity	NPC126723
0.7105	Intermediate Similarity	NPC602263
0.6923	Remote Similarity	NPC134254
0.679	Remote Similarity	NPC472653
0.6667	Remote Similarity	NPC475381
0.6582	Remote Similarity	NPC107646
0.65	Remote Similarity	NPC335761
0.642	Remote Similarity	NPC302369
0.6341	Remote Similarity	NPC209364
0.6341	Remote Similarity	NPC605015
0.6333	Remote Similarity	NPC472652
0.625	Remote Similarity	NPC472651
0.6235	Remote Similarity	NPC476853
0.6098	Remote Similarity	NPC470939
0.6098	Remote Similarity	NPC39986
0.5882	Remote Similarity	NPC609366
0.5814	Remote Similarity	NPC305016
0.5778	Remote Similarity	NPC469846
0.5747	Remote Similarity	NPC611267
0.5581	Remote Similarity	NPC263265
0.5506	Remote Similarity	NPC117986
0.5444	Remote Similarity	NPC271235
0.5422	Remote Similarity	NPC604270
0.5294	Remote Similarity	NPC60973
0.5294	Remote Similarity	NPC605384
0.5287	Remote Similarity	NPC470941
0.5275	Remote Similarity	NPC604177
0.5227	Remote Similarity	NPC286722
0.5217	Remote Similarity	NPC25255
0.5165	Remote Similarity	NPC476856
0.5161	Remote Similarity	NPC302392
0.5114	Remote Similarity	NPC5079
0.5111	Remote Similarity	NPC96443
0.5111	Remote Similarity	NPC473473
0.5111	Remote Similarity	NPC290400
0.5111	Remote Similarity	NPC475295
0.5109	Remote Similarity	NPC476858

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC173923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3837
0.1-0.2	5281
0.2-0.3	32
0.3-0.4	0
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