NPASS Compound

Natural Product: NPC51160

Natural Product ID	NPC51160
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FGBRCLVMUKRABR-ZQSRMBIWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5319226
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 87 0 0 0 0 0 0 0 0999 V2000 -5.7290 3.0916 0.2152 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8586 1.9500 0.6767 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8658 1.9646 2.1908 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2888 0.6222 0.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4216 -0.5031 0.5978 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9673 -0.3834 0.2195 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2499 -1.5629 0.7456 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0077 -2.7987 0.2110 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8325 -1.7742 0.3792 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5824 -1.9245 -1.1072 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2175 -0.7690 -1.5809 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6467 -0.0103 -0.3530 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0643 0.3589 -0.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5554 0.8132 -1.5123 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.2148 -1.6513 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5748 1.2826 -2.7306 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6185 1.5462 -0.3286 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0773 1.7938 -0.5548 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7829 0.6083 -1.1067 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3589 -0.7118 -0.5699 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8717 -0.8479 -0.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3929 0.2933 0.4962 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1186 0.3300 1.8102 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9084 0.2398 0.8028 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5895 -0.9285 1.6630 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4405 -1.7310 1.2111 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2216 -0.8600 0.8293 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0227 0.0265 1.9849 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0223 -1.0843 0.5986 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1541 0.7600 -0.7907 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0508 1.2274 -0.3282 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3839 -1.6949 2.1361 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8635 -0.2391 -1.1598 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5999 0.6266 -1.3239 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0226 -0.7692 -1.7497 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7472 1.4349 -1.5206 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8100 2.8829 0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5167 4.0000 0.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5442 3.3777 -0.8438 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8269 2.2019 0.3566 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0480 2.9990 2.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9468 1.5273 2.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7109 1.3478 2.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2898 0.4227 0.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8520 -1.4735 0.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4995 -0.5227 1.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6320 0.5881 0.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8180 -3.0922 0.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2986 -3.6441 0.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4909 -2.5766 -0.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6338 -2.8241 0.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0091 -2.8767 -1.3370 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5319 -2.0696 -1.6699 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0729 -1.1423 -2.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3770 -0.1500 -2.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9530 0.9226 -2.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1172 2.4295 0.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1516 2.6159 -1.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5288 2.2149 0.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7614 0.6330 -2.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6363 -1.4916 -1.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4031 -0.8029 -1.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6905 -1.8461 0.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2530 -0.7260 2.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4963 0.8528 2.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0883 0.8225 1.7858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7227 1.1689 1.4199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5413 -0.6529 2.7620 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4866 -1.6161 1.6479 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0937 -2.3964 2.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7158 -2.3982 0.3693 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5433 -0.2988 2.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0398 0.1594 2.3357 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3689 1.0789 1.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9927 -1.0329 0.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2590 1.3735 -0.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2394 1.7074 -1.1339 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0490 -2.5630 2.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4800 0.6093 -1.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7849 0.9258 -1.9871 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6954 -1.2473 -1.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6647 -0.6270 -2.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1853 -1.3866 -2.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4665 1.0040 -0.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 20 29 1 0 19 30 1 0 12 31 1 0 7 32 1 1 6 33 1 0 4 34 1 0 34 35 1 0 34 36 1 0 27 9 1 0 27 12 1 0 24 13 1 0 22 17 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 3 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 5 45 1 0 5 46 1 0 6 47 1 0 8 48 1 0 8 49 1 0 8 50 1 0 9 51 1 1 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 14 56 1 0 17 57 1 1 18 58 1 0 18 59 1 0 19 60 1 6 20 61 1 6 21 62 1 0 21 63 1 0 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 31 77 1 0 32 78 1 0 33 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 M END

Standard InCHIKey	FGBRCLVMUKRABR-ZQSRMBIWSA-N
Standard InCHI	InChI=1S/C29H48O7/c1-15(2)17(16(3)30)11-25(34)28(6,35)24-8-10-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,4)18(19)7-9-27(24,29)5/h12,15-18,20,22-25,30,32-36H,7-11,13-14H2,1-6H3/t16?,17?,18?,20-,22+,23-,24-,25?,26+,27+,28+,29?/m0/s1
SMILES	CC(C)C(CC([C@@](C)([C@H]1CCC2(C3=CC(=O)[C@@H]4C[C@H]([C@H](C[C@]4(C)C3CC[C@]12C)O)O)O)O)O)C(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	508.34	Volume:	532.173 ? Van der Waals volume.
Dense:	0.955	LogP:	2.158 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.57 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.676 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	138.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.324	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.374	Fsp³:	0.897
MCE-18:	87.818 ? 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:	0.277	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.215	Promiscuous compounds:	0.156

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.805	MDCK Permeability:	-4.699
Pgp-inhibitor:	0.0	Pgp-substrate:	0.39
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):	0.006
20% Bioavailability (F20%):	0.651	30% Bioavailability (F30%):	0.451
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.978
Plasma Protein Binding (PPB):	76.34%	Volume Distribution (VD):	-0.201
Fu:	24.552% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	0.952	BCRP inhibitor:	0.002
BSEP inhibitor:	0.059

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.1	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.879	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.78
HLM stability:	0.729 ? 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):

7.464

Half-life (T1/2):

2.402

ADMET: Toxicity

hERG Blockers:	0.064	hERG Blockers (10um):	0.428
Human Hepatotoxicity (H-HT):	0.827	Drug-induced Liver Injury (DILI):	0.023
AMES Toxicity:	0.058	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.823	Skin Sensitization:	0.24
Carcinogencity:	0.876	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.19
Drug-induced Neurotoxicity:	0.107	Ototoxicity:	0.989
Hematotoxicity:	0.056	Drug-induced Nephrotoxicity:	0.617
Genotoxicity:	0.321	RPMI-8226 Immunitoxicity:	0.107
A549 Cytotoxicity:	0.124	Hek293 Cytotoxicity:	0.621
BCF:	0.581 ? 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:	3.438 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.232 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.147 ? 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
NPO11283	Ajuga chamaepitys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38732407]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11283	Ajuga chamaepitys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11283	Ajuga chamaepitys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11283	Ajuga chamaepitys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11283	Ajuga chamaepitys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11283	Ajuga chamaepitys	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27558	Podocarpus macrophyllus	Species	Podocarpaceae	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 NPC51160 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	19857
0.1-0.2	27381
0.2-0.3	2555
0.3-0.4	11
0.4-0.5	6
0.5-0.6	10
0.6-0.7	14
0.7-0.8	0
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8793	High Similarity	NPC475060
0.8793	High Similarity	NPC85829
0.8475	Intermediate Similarity	NPC214264
0.8333	Intermediate Similarity	NPC296945
0.8167	Intermediate Similarity	NPC50692
0.8167	Intermediate Similarity	NPC260268
0.8167	Intermediate Similarity	NPC48733
0.8167	Intermediate Similarity	NPC171137
0.8167	Intermediate Similarity	NPC152695
0.8167	Intermediate Similarity	NPC319077
0.8167	Intermediate Similarity	NPC83744
0.8167	Intermediate Similarity	NPC97202
0.8167	Intermediate Similarity	NPC601752
0.8033	Intermediate Similarity	NPC220229
0.8033	Intermediate Similarity	NPC601682
0.7937	Intermediate Similarity	NPC476027
0.7778	Intermediate Similarity	NPC202167
0.7778	Intermediate Similarity	NPC49958
0.7692	Intermediate Similarity	NPC49492
0.7692	Intermediate Similarity	NPC266728
0.7313	Intermediate Similarity	NPC600136
0.7143	Intermediate Similarity	NPC302607
0.7121	Intermediate Similarity	NPC317210
0.7015	Intermediate Similarity	NPC207251
0.6769	Remote Similarity	NPC76084
0.662	Remote Similarity	NPC109973
0.6615	Remote Similarity	NPC204833
0.6615	Remote Similarity	NPC209502
0.6515	Remote Similarity	NPC329417
0.6462	Remote Similarity	NPC150531
0.6364	Remote Similarity	NPC477915
0.6364	Remote Similarity	NPC600374
0.6301	Remote Similarity	NPC475041
0.6269	Remote Similarity	NPC149047
0.6119	Remote Similarity	NPC11710
0.6119	Remote Similarity	NPC217201
0.6119	Remote Similarity	NPC451956
0.6119	Remote Similarity	NPC610677
0.5938	Remote Similarity	NPC603391
0.5753	Remote Similarity	NPC250109
0.5658	Remote Similarity	NPC600372
0.5541	Remote Similarity	NPC326542
0.5541	Remote Similarity	NPC606024
0.5366	Remote Similarity	NPC28532
0.5286	Remote Similarity	NPC108721
0.5286	Remote Similarity	NPC73300
0.52	Remote Similarity	NPC222688
0.507	Remote Similarity	NPC154072

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC51160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6878
0.1-0.2	2140
0.2-0.3	132
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