NPASS Compound

Natural Product: NPC107451

Natural Product ID	NPC107451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WPFUJZSUCOTGBP-IARMRDIWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318405
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

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 80 84 0 0 0 0 0 0 0 0999 V2000 -7.9221 -3.9047 0.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0374 -2.7700 -0.4089 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1056 -1.7454 -0.3474 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0676 -1.8246 0.5553 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1059 -0.8204 0.6551 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2484 0.2536 -0.1954 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2884 0.3506 -1.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2264 -0.6634 -1.1855 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2823 -0.6083 -2.0866 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5155 -0.0128 -1.7330 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4254 1.4187 -1.9542 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5633 2.5246 -2.0066 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9778 -0.8653 1.6167 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6986 -1.3671 1.0725 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5854 -1.5144 -0.3923 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4524 -0.8666 -0.8348 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0915 0.0790 0.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3740 0.1789 0.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2118 -0.9067 0.4559 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5690 -0.7894 0.6582 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1067 0.4749 0.7190 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3153 1.5939 0.5819 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9590 1.4241 0.3806 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8449 2.8739 0.6410 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0411 4.0294 0.5014 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4563 0.6862 0.9193 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4242 0.7949 -0.1064 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1959 2.1014 0.0004 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6714 1.7622 0.0324 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9269 0.9043 -1.2079 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1541 -0.3823 -1.0264 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1054 -1.5611 -0.8400 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8480 -1.3966 0.3134 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2828 -0.2897 0.0568 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3632 1.5771 -2.2788 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9864 0.9878 1.1399 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9940 2.8992 -1.1248 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3542 -1.9016 0.7943 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9100 -3.2224 0.7486 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7045 -0.3007 1.4157 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5430 0.8274 1.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7798 0.3450 2.2531 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0007 -4.4384 0.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8297 -4.5046 0.4704 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7664 -3.5525 1.5185 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9525 -2.6621 1.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5251 1.0378 -0.1404 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1835 -0.8110 -1.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0056 0.5033 -2.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3456 0.6747 -0.8568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0200 3.3073 -2.6547 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4198 2.9991 -1.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5712 2.3010 -2.4044 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2869 -1.5725 2.4474 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3426 -2.3028 1.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4227 -2.6083 -0.6293 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4728 -1.2388 -0.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4683 1.0559 -0.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7363 -1.8779 0.3993 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3423 2.3210 0.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6437 4.9220 0.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1943 4.0319 1.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5741 4.0572 -0.5234 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9750 0.6914 -1.1260 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9255 2.6264 0.9447 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2537 2.7036 0.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0176 0.7313 -1.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5278 -0.6282 -1.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7877 -1.6090 -1.7054 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5259 -2.5068 -0.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7626 -1.1103 0.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0503 1.6773 -2.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5692 1.4225 1.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3025 2.5415 -1.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2884 -3.5317 1.6078 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8190 -3.8829 0.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4414 -3.4129 -0.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9489 -0.6251 2.1557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0441 1.2545 2.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6043 1.6427 1.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 7 11 1 0 11 12 1 0 5 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 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 29 36 1 0 28 37 1 0 20 38 1 0 38 39 1 0 17 40 1 0 40 41 1 0 41 42 1 0 8 3 1 0 42 13 1 0 40 14 1 0 23 18 1 0 34 27 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 6 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 17 58 1 0 19 59 1 0 23 60 1 0 25 61 1 0 25 62 1 0 25 63 1 0 27 64 1 6 28 65 1 1 29 66 1 6 30 67 1 6 31 68 1 6 32 69 1 0 32 70 1 0 33 71 1 0 35 72 1 0 36 73 1 0 37 74 1 0 39 75 1 0 39 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 41 80 1 0 M END

Standard InCHIKey	WPFUJZSUCOTGBP-IARMRDIWSA-N
Standard InCHI	InChI=1S/C29H38O13/c1-34-17-6-13(7-18(35-2)27(17)38-5)25-15-11-40-26(16(15)12-39-25)14-8-19(36-3)28(20(9-14)37-4)42-29-24(33)23(32)22(31)21(10-30)41-29/h6-9,15-16,21-26,29-33H,10-12H2,1-5H3/t15?,16?,21-,22-,23+,24-,25?,26?,29+/m1/s1
SMILES	COc1cc(cc(c1OC)OC)C1C2COC(c3cc(c(c(c3)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)OC)C2CO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.23	Volume:	565.812 ? Van der Waals volume.
Dense:	1.05	LogP:	0.22 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.776 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.976 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	27.0
TPSA:	163.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.308	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.581	Fsp³:	0.586
MCE-18:	111.304 ? 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:	0.437	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.187 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.103	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.497	MDCK Permeability:	-5.087
Pgp-inhibitor:	0.001	Pgp-substrate:	0.032
PAMPA:	0.058 ? 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):	0.016
20% Bioavailability (F20%):	0.013	30% Bioavailability (F30%):	0.107
50% Bioavailability (F50%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872	MRP1:	0.88
Plasma Protein Binding (PPB):	76.168%	Volume Distribution (VD):	-0.356
Fu:	24.735% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.194
BSEP inhibitor:	0.535

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.166	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.295
CYP3A4-inhibitor:	0.685	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.928
HLM stability:	0.028 ? 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):

3.049

Half-life (T1/2):

3.567

ADMET: Toxicity

hERG Blockers:	0.073	hERG Blockers (10um):	0.194
Human Hepatotoxicity (H-HT):	0.789	Drug-induced Liver Injury (DILI):	0.975
AMES Toxicity:	0.771	Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.19	Skin Sensitization:	0.89
Carcinogencity:	0.158	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.043
Drug-induced Neurotoxicity:	0.211	Ototoxicity:	0.983
Hematotoxicity:	0.453	Drug-induced Nephrotoxicity:	0.653
Genotoxicity:	0.839	RPMI-8226 Immunitoxicity:	0.317
A549 Cytotoxicity:	0.314	Hek293 Cytotoxicity:	0.363
BCF:	1.073 ? 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:	3.366 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.101 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.849 ? 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
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	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 NPC107451 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	20458
0.1-0.2	25577
0.2-0.3	2865
0.3-0.4	684
0.4-0.5	201
0.5-0.6	29
0.6-0.7	18
0.7-0.8	0
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC95392
0.9804	High Similarity	NPC84013
0.9804	High Similarity	NPC55715
0.9804	High Similarity	NPC35877
0.8621	High Similarity	NPC216129
0.8621	High Similarity	NPC130449
0.8621	High Similarity	NPC248132
0.8167	Intermediate Similarity	NPC486104
0.8167	Intermediate Similarity	NPC486102
0.8065	Intermediate Similarity	NPC51328
0.8065	Intermediate Similarity	NPC55158
0.7627	Intermediate Similarity	NPC276753
0.7627	Intermediate Similarity	NPC205796
0.75	Intermediate Similarity	NPC246947
0.7213	Intermediate Similarity	NPC486107
0.7164	Intermediate Similarity	NPC486100
0.7164	Intermediate Similarity	NPC486101
0.697	Remote Similarity	NPC286235
0.6618	Remote Similarity	NPC38041
0.6618	Remote Similarity	NPC22150
0.6618	Remote Similarity	NPC279298
0.6575	Remote Similarity	NPC486099
0.6528	Remote Similarity	NPC486098
0.6429	Remote Similarity	NPC299144
0.6338	Remote Similarity	NPC605526
0.6286	Remote Similarity	NPC486109
0.6286	Remote Similarity	NPC486108
0.6207	Remote Similarity	NPC69513
0.6197	Remote Similarity	NPC486105
0.6102	Remote Similarity	NPC48863
0.6102	Remote Similarity	NPC251981
0.6102	Remote Similarity	NPC13745
0.6066	Remote Similarity	NPC162093
0.6056	Remote Similarity	NPC486106
0.6	Remote Similarity	NPC215833
0.5902	Remote Similarity	NPC49074
0.5897	Remote Similarity	NPC486097
0.5893	Remote Similarity	NPC217854
0.5714	Remote Similarity	NPC276195
0.5714	Remote Similarity	NPC210478
0.5692	Remote Similarity	NPC232673
0.569	Remote Similarity	NPC152722
0.5686	Remote Similarity	NPC281864
0.5686	Remote Similarity	NPC328682
0.5686	Remote Similarity	NPC54321
0.5658	Remote Similarity	NPC186316
0.5625	Remote Similarity	NPC479029
0.5616	Remote Similarity	NPC471063
0.5606	Remote Similarity	NPC470236
0.5584	Remote Similarity	NPC486103
0.5513	Remote Similarity	NPC478055
0.5441	Remote Similarity	NPC479030
0.5323	Remote Similarity	NPC95292
0.5256	Remote Similarity	NPC39657
0.52	Remote Similarity	NPC199539
0.5179	Remote Similarity	NPC473092
0.5179	Remote Similarity	NPC473093
0.5179	Remote Similarity	NPC8050
0.5172	Remote Similarity	NPC165155
0.5172	Remote Similarity	NPC24490
0.5125	Remote Similarity	NPC185307
0.5079	Remote Similarity	NPC166040
0.507	Remote Similarity	NPC475084
0.5068	Remote Similarity	NPC606627

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC107451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5401
0.1-0.2	3634
0.2-0.3	101
0.3-0.4	13
0.4-0.5	1
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