NPASS Compound

Natural Product: NPC26676

Natural Product ID	NPC26676
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LISHAQDJMDPPOF-HFEPJMNKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321999
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids 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 86 90 0 0 0 0 0 0 0 0999 V2000 -2.1747 3.3850 3.0259 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4116 2.9191 1.6391 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0695 3.5622 0.7956 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8685 1.7000 1.2651 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0604 1.1905 -0.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3335 -0.1385 -0.1004 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9954 -0.9884 0.9649 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1206 -1.8444 0.4942 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8482 -1.4105 -0.7233 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9590 -0.9652 -1.8585 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4794 0.2603 -2.5542 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5469 -0.8864 -1.3884 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6002 -0.4059 -2.4449 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 -1.1453 -1.9412 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1299 -0.3241 -0.7823 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0994 0.1368 0.1864 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3770 1.4998 0.4649 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 1.9639 1.6703 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0113 1.0558 2.5558 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1266 3.3497 1.9572 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5841 3.7128 3.1961 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8677 5.0571 3.4900 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6812 6.0063 2.5207 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2316 5.6200 1.3154 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 4.3212 1.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1893 -1.0495 -0.1795 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5173 -0.6535 -0.2484 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7427 0.4102 -0.8883 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5894 -1.3944 0.3643 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8739 -0.9348 0.2484 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8979 -1.6311 0.8239 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5981 -2.7975 1.5168 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3088 -3.2418 1.6225 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2641 -2.5491 1.0464 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0616 -2.4644 -1.5735 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1203 -3.3769 -2.8011 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8492 -3.2061 -0.5107 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1917 -2.2323 -1.1117 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9429 -0.7914 -3.7291 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0523 0.1270 -4.7594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8228 1.3300 -4.4710 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4264 -0.2786 -6.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9467 -1.9883 -2.8461 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3514 -0.2427 2.1124 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7799 -0.4585 3.3364 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 -1.3760 3.4105 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1345 0.3080 4.5702 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8843 4.4785 3.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0335 3.2061 3.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2958 2.8740 3.4663 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1315 1.1303 -0.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5471 1.9518 -0.6981 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1919 -1.7105 1.3088 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8776 -1.8693 1.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8349 -2.9331 0.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4358 -2.3131 -1.0747 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6760 -0.6670 -0.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7247 0.0833 -3.6406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7567 1.0987 -2.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4730 0.5894 -2.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4463 0.6803 -2.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4418 -1.1748 -2.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6341 0.5648 -1.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3346 -0.4070 1.1548 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7528 3.0276 3.9999 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2306 5.3536 4.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8828 7.0611 2.6872 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5949 4.1006 0.0195 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1011 -0.0099 -0.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9343 -1.3398 0.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3889 -3.3478 1.9689 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0569 -4.1594 2.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2560 -2.9228 1.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1793 -4.3965 -2.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 -3.0822 -3.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1692 -3.3844 -3.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8930 -3.4059 -0.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3736 -4.2301 -0.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7768 -2.7774 0.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4903 -0.1765 -6.7626 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7894 -1.3057 -6.1646 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1393 0.4654 -6.5812 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1147 -1.6537 -3.7378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4515 -0.4063 5.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0379 0.8966 4.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3266 0.9709 4.9040 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 6 5 1 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 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 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 15 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 14 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 13 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 10 43 1 6 7 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 16 6 1 0 25 20 1 0 34 29 1 0 12 6 1 0 38 12 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 0 5 52 1 0 7 53 1 0 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 11 58 1 0 11 59 1 0 11 60 1 0 13 61 1 0 14 62 1 0 15 63 1 0 16 64 1 1 21 65 1 0 22 66 1 0 23 67 1 0 25 68 1 0 30 69 1 0 31 70 1 0 32 71 1 0 33 72 1 0 34 73 1 0 36 74 1 0 36 75 1 0 36 76 1 0 37 77 1 0 37 78 1 0 37 79 1 0 42 80 1 0 42 81 1 0 42 82 1 0 43 83 1 0 47 84 1 0 47 85 1 0 47 86 1 0 M END

Standard InCHIKey	LISHAQDJMDPPOF-HFEPJMNKSA-N
Standard InCHI	InChI=1S/C34H39NO12/c1-19(36)42-18-33-24(43-20(2)37)14-15-32(6,41)34(33)27(44-21(3)38)25(31(4,5)47-34)26(45-29(39)22-11-8-7-9-12-22)28(33)46-30(40)23-13-10-16-35-17-23/h7-13,16-17,24-28,41H,14-15,18H2,1-6H3/t24?,25?,26?,27?,28-,32+,33+,34?/m1/s1
SMILES	CC(=O)OC[C@]12C(CC[C@@](C)(C32C(C(C([C@H]1OC(=O)c1cccnc1)OC(=O)c1ccccc1)C(C)(C)O3)OC(=O)C)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	653.25	Volume:	641.316 ? Van der Waals volume.
Dense:	1.019	LogP:	2.837 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.738 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.687 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	31.0
TPSA:	173.85 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.326	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.904	Fsp³:	0.529
MCE-18:	172.5 ? 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:	0.025	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.282 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.014	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.369	MDCK Permeability:	-4.746
Pgp-inhibitor:	0.989	Pgp-substrate:	0.086
PAMPA:	0.956 ? 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%):	0.044	30% Bioavailability (F30%):	0.232
50% Bioavailability (F50%):	0.817

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	56.605%	Volume Distribution (VD):	-0.263
Fu:	45.296% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.98	BCRP inhibitor:	0.005
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.017	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.107

Half-life (T1/2):

1.204

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.425
Human Hepatotoxicity (H-HT):	0.158	Drug-induced Liver Injury (DILI):	0.597
AMES Toxicity:	0.296	Rat Oral Acute Toxicity:	0.434
Maximum Recommended Daily Dose:	0.482	Skin Sensitization:	0.551
Carcinogencity:	0.657	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.421	Ototoxicity:	0.496
Hematotoxicity:	0.02	Drug-induced Nephrotoxicity:	0.366
Genotoxicity:	0.673	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.024	Hek293 Cytotoxicity:	0.184
BCF:	0.878 ? 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:	3.667 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.552 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.043 ? 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
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	anomalous fruits	n.a.	n.a.	PMID[25442304]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16101	Gleditsia triacanthos	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20608	Gleditsia sinensis	Species	Fabaceae	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 NPC26676 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	13335
0.1-0.2	34105
0.2-0.3	1784
0.3-0.4	390
0.4-0.5	151
0.5-0.6	65
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.859	High Similarity	NPC180668
0.8125	Intermediate Similarity	NPC10904
0.7821	Intermediate Similarity	NPC481064
0.7683	Intermediate Similarity	NPC148896
0.7614	Intermediate Similarity	NPC6981
0.7436	Intermediate Similarity	NPC57628
0.7375	Intermediate Similarity	NPC481062
0.7375	Intermediate Similarity	NPC481058
0.7375	Intermediate Similarity	NPC481060
0.7349	Intermediate Similarity	NPC301368
0.7349	Intermediate Similarity	NPC84815
0.7024	Intermediate Similarity	NPC610927
0.6951	Remote Similarity	NPC294803
0.6742	Remote Similarity	NPC483885
0.6667	Remote Similarity	NPC473115
0.6585	Remote Similarity	NPC11685
0.6522	Remote Similarity	NPC471013
0.6374	Remote Similarity	NPC479045
0.6341	Remote Similarity	NPC171207
0.619	Remote Similarity	NPC472569
0.619	Remote Similarity	NPC16912
0.6118	Remote Similarity	NPC481063
0.6067	Remote Similarity	NPC611111
0.6022	Remote Similarity	NPC176413
0.6022	Remote Similarity	NPC294512
0.593	Remote Similarity	NPC127720
0.5904	Remote Similarity	NPC163719
0.5904	Remote Similarity	NPC483845
0.5904	Remote Similarity	NPC95810
0.5876	Remote Similarity	NPC294579
0.5876	Remote Similarity	NPC144779
0.5843	Remote Similarity	NPC4421
0.5824	Remote Similarity	NPC6576
0.5814	Remote Similarity	NPC472570
0.5795	Remote Similarity	NPC481489
0.5778	Remote Similarity	NPC488900
0.5761	Remote Similarity	NPC127026
0.5761	Remote Similarity	NPC483890
0.573	Remote Similarity	NPC481488
0.573	Remote Similarity	NPC481486
0.567	Remote Similarity	NPC488902
0.567	Remote Similarity	NPC488903
0.5667	Remote Similarity	NPC212768
0.5604	Remote Similarity	NPC488899
0.5595	Remote Similarity	NPC281717
0.5591	Remote Similarity	NPC75600
0.5591	Remote Similarity	NPC483884
0.5568	Remote Similarity	NPC70716
0.5568	Remote Similarity	NPC97667
0.5567	Remote Similarity	NPC96801
0.5567	Remote Similarity	NPC150698
0.5556	Remote Similarity	NPC271460
0.5556	Remote Similarity	NPC483887
0.5556	Remote Similarity	NPC158020
0.5543	Remote Similarity	NPC125106
0.5543	Remote Similarity	NPC472573
0.5529	Remote Similarity	NPC90257
0.5529	Remote Similarity	NPC69357
0.5495	Remote Similarity	NPC479049
0.5474	Remote Similarity	NPC253738
0.5464	Remote Similarity	NPC483868
0.5444	Remote Similarity	NPC483849
0.5444	Remote Similarity	NPC479042
0.5402	Remote Similarity	NPC471104
0.5393	Remote Similarity	NPC95265
0.5376	Remote Similarity	NPC479048
0.5361	Remote Similarity	NPC479046
0.5341	Remote Similarity	NPC483844
0.5333	Remote Similarity	NPC282239
0.5333	Remote Similarity	NPC471102
0.5326	Remote Similarity	NPC608007
0.53	Remote Similarity	NPC471980
0.5281	Remote Similarity	NPC252314
0.5281	Remote Similarity	NPC481059
0.5233	Remote Similarity	NPC51314
0.5233	Remote Similarity	NPC483886
0.5213	Remote Similarity	NPC483881
0.5172	Remote Similarity	NPC147880
0.5165	Remote Similarity	NPC147340
0.5165	Remote Similarity	NPC483848
0.5161	Remote Similarity	NPC6815
0.5158	Remote Similarity	NPC473089
0.5158	Remote Similarity	NPC479041
0.5146	Remote Similarity	NPC483880
0.5146	Remote Similarity	NPC156941
0.5114	Remote Similarity	NPC137718
0.5114	Remote Similarity	NPC148062
0.5106	Remote Similarity	NPC483889
0.5056	Remote Similarity	NPC473088
0.5055	Remote Similarity	NPC96903

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC26676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3184
0.1-0.2	5825
0.2-0.3	136
0.3-0.4	5
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