NPASS Compound

Natural Product: NPC175116

Natural Product ID	NPC175116
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HVGMINHJTDNOLV-GSXAJODKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44258449
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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 75 79 0 0 0 0 0 0 0 0999 V2000 -5.7490 3.2303 0.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0900 1.9464 0.7641 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7677 2.1387 2.2063 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6782 1.2741 2.7443 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5818 1.1484 1.7086 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2069 0.6550 0.4396 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9899 1.7287 -0.0495 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3090 0.3049 -0.5304 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4983 -0.9417 -1.0525 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5799 -0.9328 -2.5787 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0878 -2.3216 -2.9178 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5622 -3.3552 -1.9591 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5606 -4.6834 -2.6837 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7697 -4.9734 -3.2649 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3709 -3.0547 -1.3782 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2763 -1.8293 -0.7415 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0935 -1.1736 -0.9383 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0217 -0.9980 -0.2044 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0490 -0.1466 -0.6778 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2124 0.0819 0.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3974 -0.5427 1.2263 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5820 -0.3009 1.9158 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7480 -0.8653 3.0111 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4902 0.5547 1.3264 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2625 1.1560 0.1131 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2486 2.0508 -0.4695 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4260 2.3386 0.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3697 3.2080 -0.4329 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1195 3.7935 -1.6495 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9369 3.5137 -2.2834 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0188 2.6607 -1.7084 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0678 4.6623 -2.2225 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1271 0.8989 -0.5055 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4388 -1.3695 1.7204 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2657 -1.5796 0.9878 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3687 -2.4445 1.5867 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4730 -3.8553 1.3973 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6648 -1.9759 2.9405 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4787 -2.2804 -2.8383 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3424 -0.6785 -3.1187 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9953 2.4036 1.5538 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1900 1.8917 3.9085 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5658 3.5036 2.5134 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1642 4.0694 0.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7693 3.2610 0.6944 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7592 3.2808 -0.8463 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8661 1.1420 0.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7018 1.8707 2.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0772 0.2673 2.9734 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7960 0.4774 2.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -0.1402 0.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3572 -1.4898 -0.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3020 -0.2138 -2.9628 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8070 -2.5529 -3.9457 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3202 -3.4503 -1.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2838 -5.5271 -2.0206 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7946 -4.6893 -3.5100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9798 -5.9496 -3.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4136 -2.0597 0.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8694 0.3266 -1.6324 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4012 0.7096 1.9078 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6847 1.9158 1.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3078 3.4221 0.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7292 3.9676 -3.2407 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0666 2.4066 -2.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6424 5.2303 -1.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7211 -4.0898 0.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4911 -4.3624 1.6027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2387 -4.3019 2.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3134 -2.7213 3.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7824 -2.5497 -1.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7674 -1.4900 -3.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2930 3.0725 2.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3858 1.3752 4.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4431 3.9510 2.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 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 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 25 33 1 0 21 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 34 38 1 0 11 39 1 0 10 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 7 2 1 0 16 9 1 0 35 18 1 0 33 20 1 0 31 26 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 3 48 1 1 4 49 1 1 5 50 1 0 6 51 1 1 9 52 1 0 10 53 1 1 11 54 1 6 12 55 1 0 13 56 1 0 13 57 1 0 14 58 1 0 16 59 1 1 19 60 1 0 24 61 1 0 27 62 1 0 28 63 1 0 30 64 1 0 31 65 1 0 32 66 1 0 37 67 1 0 37 68 1 0 37 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	HVGMINHJTDNOLV-GSXAJODKSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-19(32)22(35)24(37)27(39-10)43-26-23(36)20(33)17(9-29)42-28(26)41-16-8-15-18(21(34)25(16)38-2)13(31)7-14(40-15)11-3-5-12(30)6-4-11/h3-8,10,17,19-20,22-24,26-30,32-37H,9H2,1-2H3/t10?,17?,19-,20+,22-,23-,24?,26?,27-,28+/m0/s1
SMILES	CC1[C@@H]([C@@H](C([C@@H](O1)OC1[C@H]([C@@H](C(CO)O[C@H]1Oc1cc2c(c(=O)cc(c3ccc(cc3)O)o2)c(c1OC)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	0.05 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.921 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.003 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.702	Fsp³:	0.464
MCE-18:	118.585 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.594	Fluc inhibitor:	0.193 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.883 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.948 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.144	Promiscuous compounds:	0.297

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.345	MDCK Permeability:	-5.275
Pgp-inhibitor:	0.0	Pgp-substrate:	0.982
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):	0.957
20% Bioavailability (F20%):	0.927	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.782
Plasma Protein Binding (PPB):	83.464%	Volume Distribution (VD):	-0.005
Fu:	15.174% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.889
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.24
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.434	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.98
HLM stability:	0.135 ? 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):

1.249

Half-life (T1/2):

2.956

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.205
Human Hepatotoxicity (H-HT):	0.532	Drug-induced Liver Injury (DILI):	0.923
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.258	Skin Sensitization:	0.98
Carcinogencity:	0.3	Eye Corrosion:	0.0
Eye Irritation:	0.102	Respiratory Toxicity:	0.047
Drug-induced Neurotoxicity:	0.032	Ototoxicity:	0.911
Hematotoxicity:	0.156	Drug-induced Nephrotoxicity:	0.232
Genotoxicity:	0.927	RPMI-8226 Immunitoxicity:	0.166
A549 Cytotoxicity:	0.539	Hek293 Cytotoxicity:	0.839
BCF:	0.344 ? 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:	2.825 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.569 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.548 ? 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
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21899269]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20096	Cirsium japonicum	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

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 NPC175116 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	21310
0.1-0.2	23876
0.2-0.3	3709
0.3-0.4	617
0.4-0.5	251
0.5-0.6	59
0.6-0.7	22
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
0.7791	Intermediate Similarity	NPC65003
0.7229	Intermediate Similarity	NPC105025
0.7045	Intermediate Similarity	NPC473682
0.6923	Remote Similarity	NPC115674
0.6915	Remote Similarity	NPC195257
0.6905	Remote Similarity	NPC93337
0.6667	Remote Similarity	NPC240306
0.6559	Remote Similarity	NPC470444
0.6437	Remote Similarity	NPC186807
0.6395	Remote Similarity	NPC58053
0.6364	Remote Similarity	NPC201292
0.6304	Remote Similarity	NPC8856
0.6238	Remote Similarity	NPC473072
0.6224	Remote Similarity	NPC473071
0.6211	Remote Similarity	NPC204693
0.6186	Remote Similarity	NPC32641
0.6186	Remote Similarity	NPC256188
0.617	Remote Similarity	NPC163242
0.617	Remote Similarity	NPC272068
0.6154	Remote Similarity	NPC602805
0.6132	Remote Similarity	NPC298666
0.6067	Remote Similarity	NPC45638
0.6061	Remote Similarity	NPC475382
0.6058	Remote Similarity	NPC311850
0.602	Remote Similarity	NPC35119
0.5934	Remote Similarity	NPC609451
0.5876	Remote Similarity	NPC257566
0.5876	Remote Similarity	NPC122809
0.587	Remote Similarity	NPC605067
0.5851	Remote Similarity	NPC172807
0.5773	Remote Similarity	NPC155877
0.5769	Remote Similarity	NPC120163
0.5743	Remote Similarity	NPC220173
0.5741	Remote Similarity	NPC68592
0.573	Remote Similarity	NPC331652
0.5688	Remote Similarity	NPC198199
0.5667	Remote Similarity	NPC39360
0.5667	Remote Similarity	NPC29763
0.5667	Remote Similarity	NPC210003
0.5657	Remote Similarity	NPC606547
0.5604	Remote Similarity	NPC146792
0.5579	Remote Similarity	NPC170052
0.5579	Remote Similarity	NPC135846
0.5543	Remote Similarity	NPC24043
0.5532	Remote Similarity	NPC80188
0.5524	Remote Similarity	NPC11468
0.5521	Remote Similarity	NPC211594
0.551	Remote Similarity	NPC44931
0.55	Remote Similarity	NPC472992
0.549	Remote Similarity	NPC142142
0.5439	Remote Similarity	NPC262222
0.5417	Remote Similarity	NPC476215
0.5398	Remote Similarity	NPC120952
0.5376	Remote Similarity	NPC610763
0.537	Remote Similarity	NPC473644
0.537	Remote Similarity	NPC25523
0.5333	Remote Similarity	NPC253685
0.5333	Remote Similarity	NPC602448
0.5306	Remote Similarity	NPC44947
0.5306	Remote Similarity	NPC239549
0.5294	Remote Similarity	NPC483414
0.5273	Remote Similarity	NPC488083
0.5269	Remote Similarity	NPC95090
0.5269	Remote Similarity	NPC27408
0.5243	Remote Similarity	NPC483707
0.5204	Remote Similarity	NPC254855
0.5204	Remote Similarity	NPC94610
0.5181	Remote Similarity	NPC607702
0.5161	Remote Similarity	NPC83283
0.5158	Remote Similarity	NPC117260
0.5155	Remote Similarity	NPC136761
0.5152	Remote Similarity	NPC254540
0.5149	Remote Similarity	NPC22062
0.5149	Remote Similarity	NPC473634
0.5149	Remote Similarity	NPC138811
0.5106	Remote Similarity	NPC259152
0.5104	Remote Similarity	NPC488071
0.5053	Remote Similarity	NPC10807
0.5053	Remote Similarity	NPC27640
0.5053	Remote Similarity	NPC161881
0.5052	Remote Similarity	NPC243930
0.5051	Remote Similarity	NPC95866
0.505	Remote Similarity	NPC78734
0.5048	Remote Similarity	NPC472991

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC175116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5443
0.1-0.2	3614
0.2-0.3	82
0.3-0.4	8
0.4-0.5	3
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