NPASS Compound

Natural Product: NPC168046

Natural Product ID	NPC168046
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FQJLCTDZJGECJX-ONVJOHOVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids [CHEMONTID:0003233] 3-beta-hydroxysteroids

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 82 0 0 0 0 0 0 0 0999 V2000 5.8517 -1.2629 2.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7566 -0.4182 1.3958 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5558 0.7450 2.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3523 0.1232 0.1515 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2878 0.8261 -0.6514 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3038 -0.1939 -1.1406 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9578 -0.8080 -2.3838 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9955 0.4408 -1.6531 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9660 0.0925 -0.6354 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0829 1.1020 0.4561 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4622 -1.2819 -0.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6412 -2.3016 -0.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8393 -2.2429 -0.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2317 -0.8169 -0.1484 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7062 -0.5875 -0.0379 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5332 -1.2695 -1.0527 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1468 -1.1537 1.3270 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5939 -0.9342 1.6078 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1936 0.3173 1.0706 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2307 1.3499 0.6181 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0342 2.3454 1.7786 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9481 2.1939 -0.4493 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9240 0.8924 0.0988 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5266 1.5042 -1.2096 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9978 1.4336 -1.2381 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4690 0.0232 -1.1208 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4686 -0.4862 -2.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2059 0.0500 0.1132 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9489 -1.2552 -0.1794 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5051 -1.2111 1.1921 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5204 -1.3919 3.1368 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7711 -0.6570 2.1022 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9695 -2.2218 1.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4451 0.9318 2.9832 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3422 1.6425 1.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6564 0.5267 3.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7230 -0.7202 -0.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1756 0.8142 0.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8642 1.7186 -0.1860 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8711 1.2596 -1.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6176 -0.0878 -2.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1826 -1.1223 -3.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5098 -1.7251 -2.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7880 0.1643 -2.6780 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2131 1.5498 -1.6626 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2315 1.1729 1.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9930 1.0247 1.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2764 2.0960 -0.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1226 -3.2688 0.1818 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1098 -2.7506 -1.2052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2447 -2.8952 0.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8506 -0.4839 0.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9377 -2.0637 -1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3910 -1.8680 -0.6114 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0385 -0.6071 -1.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9985 -2.2635 1.3535 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4684 -0.7345 2.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7034 -1.0176 2.7316 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2350 -1.7889 1.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8086 0.7592 1.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9683 1.7762 2.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8035 3.1181 1.7828 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0394 2.7940 1.6019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7717 1.8411 -1.4604 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5418 3.2474 -0.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0133 2.2978 -0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1410 1.2171 0.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7559 2.6005 -1.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9875 1.0978 -2.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7284 1.8979 -2.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7123 2.0887 -0.3760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1544 0.3459 -3.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5058 -0.7245 -2.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1123 -1.4072 -2.6791 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9857 0.3568 -0.7777 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -2.2273 -0.6127 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7845 -2.2664 1.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7297 -0.9961 1.9964 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 6 6 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 19 28 1 0 11 29 1 0 29 30 1 0 30 2 1 0 29 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 10 46 1 0 10 47 1 0 10 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 14 52 1 1 16 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 1 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 22 66 1 0 23 67 1 1 24 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 27 72 1 0 27 73 1 0 27 74 1 0 28 75 1 0 29 76 1 6 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	FQJLCTDZJGECJX-ONVJOHOVSA-N
Standard InCHI	InChI=1S/C29H48O/c1-24(2)15-16-26(5)18-29(8)19(20(26)17-24)9-10-22-27(6)13-12-23(30)25(3,4)21(27)11-14-28(22,29)7/h9,20-23,30H,10-18H2,1-8H3/t20-,21-,22+,23-,26+,27-,28+,29+/m0/s1
SMILES	CC1(C)CC[C@]2(C)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	473.512 ? Van der Waals volume.
Dense:	0.871	LogP:	5.455 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.572 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.257 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	25.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.403	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.696	Fsp³:	0.931
MCE-18:	101.786 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.816	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.766	Promiscuous compounds:	0.065

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.293	MDCK Permeability:	-4.978
Pgp-inhibitor:	0.925	Pgp-substrate:	0.013
PAMPA:	0.953 ? 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):	0.0
20% Bioavailability (F20%):	0.82	30% Bioavailability (F30%):	0.152
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.927
Plasma Protein Binding (PPB):	97.657%	Volume Distribution (VD):	-0.032
Fu:	2.412% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.476
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.596	CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.009	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.017	CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.723	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.905
HLM stability:	0.948 ? 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):

10.505

Half-life (T1/2):

0.149

ADMET: Toxicity

hERG Blockers:	0.076	hERG Blockers (10um):	0.257
Human Hepatotoxicity (H-HT):	0.574	Drug-induced Liver Injury (DILI):	0.369
AMES Toxicity:	0.494	Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.531	Skin Sensitization:	0.895
Carcinogencity:	0.904	Eye Corrosion:	0.12
Eye Irritation:	0.69	Respiratory Toxicity:	0.877
Drug-induced Neurotoxicity:	0.192	Ototoxicity:	0.383
Hematotoxicity:	0.605	Drug-induced Nephrotoxicity:	0.722
Genotoxicity:	0.635	RPMI-8226 Immunitoxicity:	0.07
A549 Cytotoxicity:	0.645	Hek293 Cytotoxicity:	0.534
BCF:	3.101 ? 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:	4.723 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.335 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.539 ? 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
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043423]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29182349]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10409	Methanothermobacter thermautotrophicus	Species	Methanobacteriaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21552	Oreaster nodosus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7956	Discaria chacaye	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5447	Digitalis canariensis	Species	Plantaginaceae	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 NPC168046 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	26688
0.1-0.2	18961
0.2-0.3	3169
0.3-0.4	777
0.4-0.5	168
0.5-0.6	69
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.86	High Similarity	NPC290598
0.86	High Similarity	NPC30590
0.7455	Intermediate Similarity	NPC101475
0.7455	Intermediate Similarity	NPC34177
0.7321	Intermediate Similarity	NPC235341
0.7321	Intermediate Similarity	NPC253807
0.7321	Intermediate Similarity	NPC158662
0.7273	Intermediate Similarity	NPC474989
0.7143	Intermediate Similarity	NPC196753
0.6949	Remote Similarity	NPC246708
0.6897	Remote Similarity	NPC470588
0.6842	Remote Similarity	NPC311078
0.6613	Remote Similarity	NPC488519
0.6441	Remote Similarity	NPC480924
0.6316	Remote Similarity	NPC27765
0.6316	Remote Similarity	NPC122418
0.6316	Remote Similarity	NPC491014
0.6066	Remote Similarity	NPC53744
0.6066	Remote Similarity	NPC159168
0.6034	Remote Similarity	NPC601696
0.5968	Remote Similarity	NPC480950
0.5902	Remote Similarity	NPC475862
0.5846	Remote Similarity	NPC171203
0.5846	Remote Similarity	NPC307426
0.5846	Remote Similarity	NPC98442
0.5846	Remote Similarity	NPC242468
0.5806	Remote Similarity	NPC238992
0.5763	Remote Similarity	NPC120098
0.5735	Remote Similarity	NPC294360
0.5692	Remote Similarity	NPC480946
0.5692	Remote Similarity	NPC130577
0.5692	Remote Similarity	NPC142415
0.5692	Remote Similarity	NPC102683
0.5692	Remote Similarity	NPC2539
0.5667	Remote Similarity	NPC142754
0.5645	Remote Similarity	NPC478657
0.5606	Remote Similarity	NPC7260
0.5606	Remote Similarity	NPC210037
0.5606	Remote Similarity	NPC120968
0.5606	Remote Similarity	NPC227467
0.5606	Remote Similarity	NPC273621
0.5556	Remote Similarity	NPC230295
0.5556	Remote Similarity	NPC98386
0.5541	Remote Similarity	NPC167383
0.5484	Remote Similarity	NPC132478
0.5484	Remote Similarity	NPC237344
0.5455	Remote Similarity	NPC136313
0.5455	Remote Similarity	NPC172361
0.5455	Remote Similarity	NPC610937
0.5441	Remote Similarity	NPC228784
0.5441	Remote Similarity	NPC49776
0.5441	Remote Similarity	NPC324341
0.5441	Remote Similarity	NPC63118
0.5441	Remote Similarity	NPC164349
0.5441	Remote Similarity	NPC474436
0.5441	Remote Similarity	NPC601810
0.5397	Remote Similarity	NPC40394
0.5397	Remote Similarity	NPC195334
0.5397	Remote Similarity	NPC291379
0.5373	Remote Similarity	NPC112866
0.5345	Remote Similarity	NPC138374
0.5345	Remote Similarity	NPC472805
0.5345	Remote Similarity	NPC34700
0.5345	Remote Similarity	NPC90979
0.5312	Remote Similarity	NPC95594
0.5303	Remote Similarity	NPC477872
0.5231	Remote Similarity	NPC133954
0.5224	Remote Similarity	NPC187722
0.5224	Remote Similarity	NPC213412
0.5224	Remote Similarity	NPC198664
0.5152	Remote Similarity	NPC40552
0.5147	Remote Similarity	NPC182797
0.5147	Remote Similarity	NPC51700
0.5147	Remote Similarity	NPC88716
0.5147	Remote Similarity	NPC68160
0.5147	Remote Similarity	NPC52169
0.5147	Remote Similarity	NPC488562
0.5147	Remote Similarity	NPC606443
0.5143	Remote Similarity	NPC480919
0.5077	Remote Similarity	NPC253402
0.5077	Remote Similarity	NPC3915
0.5075	Remote Similarity	NPC17733
0.5075	Remote Similarity	NPC470629
0.5075	Remote Similarity	NPC477579
0.5072	Remote Similarity	NPC18872
0.5072	Remote Similarity	NPC290614
0.5068	Remote Similarity	NPC471433
0.5068	Remote Similarity	NPC283343
0.5068	Remote Similarity	NPC471432

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC168046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8122
0.1-0.2	977
0.2-0.3	47
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
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
0.5373	Remote Similarity	NPD7645	Phase 2

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