NPASS Compound

Natural Product: NPC493109

Natural Product ID	NPC493109
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},3~{S},4~{S},5~{R},6~{R})-6-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-carboxy-4,5-dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
IUPAC Name	(2~{R},3~{S},4~{S},5~{R},6~{R})-6-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-carboxy-4,5-dihydroxy-2-[5-hydroxy-2-(4-methoxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 73 77 0 0 0 0 0 0 0 0999 V2000 9.6800 2.3230 -3.3343 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4097 1.8491 -3.7310 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4779 1.5310 -2.7382 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7900 1.6748 -1.3977 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8470 1.3526 -0.4254 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6014 0.8910 -0.7512 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5885 0.5429 0.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8021 0.6460 1.5797 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8310 0.3125 2.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0500 0.4150 3.7559 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6164 -0.1357 2.0743 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6053 -0.4845 2.9459 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8449 -0.3723 4.2955 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3739 -0.9388 2.4508 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1750 -1.0364 1.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0164 -1.4763 0.5923 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1072 -1.8566 1.3197 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4474 -3.1828 1.0057 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4694 -3.6937 1.7569 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1268 -4.0096 3.1528 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9822 -3.8286 3.6173 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1055 -4.5246 3.9790 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7346 -2.8712 1.7604 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5351 -3.3480 2.7920 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3749 -1.3997 2.0048 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4893 -0.6087 2.0413 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3709 -1.0479 0.9361 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0715 0.2931 0.8449 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2645 0.7963 -0.4372 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0416 1.2382 -0.9854 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1800 1.3110 -2.3463 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2109 -0.0213 -3.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3445 -0.0610 -4.2578 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0986 -1.2274 -2.3430 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2747 2.2099 -2.8164 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6817 1.7449 -4.0881 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4875 2.2510 -1.9555 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0799 3.5093 -2.1036 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1788 1.9954 -0.4905 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3446 1.8634 0.2166 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2273 -0.6722 0.2624 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4469 -0.2229 0.7076 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3978 0.1053 -0.1332 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2886 0.7467 -2.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2218 1.0654 -3.0642 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3726 2.4180 -4.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1749 1.6374 -2.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6391 3.3292 -2.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7787 2.0412 -1.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1416 1.4830 0.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7585 0.9993 1.9597 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8178 0.5684 4.6875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3724 -1.1939 3.1960 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0240 -1.8338 2.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7616 -4.6646 1.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9683 -4.8659 4.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2214 -2.9431 0.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4179 -3.5675 2.3852 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8046 -1.3901 2.9762 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7872 -0.5195 2.9864 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7259 -1.4491 -0.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6393 0.0499 -1.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2200 1.7824 -2.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2164 -2.1079 -2.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9045 3.2576 -3.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4551 2.2846 -4.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1742 1.4318 -2.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9222 4.1048 -1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5609 2.8667 -0.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1269 2.0448 1.1796 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0292 -0.7638 -0.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3229 0.3884 -2.3807 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0108 0.9640 -4.1306 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 19 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 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 2 0 32 34 1 0 31 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 15 41 1 0 41 42 2 0 42 43 1 0 6 44 1 0 44 45 2 0 45 3 1 0 43 7 1 0 42 11 1 0 27 17 1 0 39 29 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 5 50 1 0 8 51 1 0 13 52 1 0 14 53 1 0 17 54 1 1 19 55 1 6 22 56 1 0 23 57 1 6 24 58 1 0 25 59 1 1 26 60 1 0 27 61 1 6 29 62 1 6 31 63 1 6 34 64 1 0 35 65 1 6 36 66 1 0 37 67 1 6 38 68 1 0 39 69 1 1 40 70 1 0 41 71 1 0 44 72 1 0 45 73 1 0 M END

Standard InCHIKey	JNGIOHRDWMHQEK-PKIYDHPSSA-N
Standard InCHI	InChI=1S/C28H28O17/c1-40-10-4-2-9(3-5-10)14-8-13(30)16-12(29)6-11(7-15(16)42-14)41-28-24(20(34)19(33)23(44-28)26(38)39)45-27-21(35)17(31)18(32)22(43-27)25(36)37/h2-8,17-24,27-29,31-35H,1H3,(H,36,37)(H,38,39)/t17-,18-,19-,20-,21+,22+,23+,24+,27-,28+/m0/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.13	Volume:	573.131 ? Van der Waals volume.
Dense:	1.11	LogP:	0.718 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.417 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.199 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	272.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.691	Fsp³:	0.393
MCE-18:	122.949 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.433	Fluc inhibitor:	0.482 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.922 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.648 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.236	Promiscuous compounds:	0.349

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.297	MDCK Permeability:	-5.232
Pgp-inhibitor:	0.0	Pgp-substrate:	0.502
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):	0.766
20% Bioavailability (F20%):	0.163	30% Bioavailability (F30%):	0.205
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.997
Plasma Protein Binding (PPB):	77.79%	Volume Distribution (VD):	-0.429
Fu:	19.997% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.008
OATP1B3 inhibitor:	0.66	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.898
HLM stability:	0.0 ? 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):

0.569

Half-life (T1/2):

4.902

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.345	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.784	Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	0.991
Carcinogencity:	0.017	Eye Corrosion:	0.0
Eye Irritation:	0.246	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.84
Hematotoxicity:	0.126	Drug-induced Nephrotoxicity:	0.863
Genotoxicity:	0.965	RPMI-8226 Immunitoxicity:	0.08
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.039
BCF:	0.1 ? 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:	2.899 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.326 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.446 ? 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
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	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 NPC493109 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	19106
0.1-0.2	27846
0.2-0.3	2166
0.3-0.4	557
0.4-0.5	126
0.5-0.6	46
0.6-0.7	8
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
0.7738	Intermediate Similarity	NPC608742
0.7447	Intermediate Similarity	NPC253685
0.6629	Remote Similarity	NPC282169
0.6444	Remote Similarity	NPC20505
0.6289	Remote Similarity	NPC46202
0.6117	Remote Similarity	NPC11468
0.6111	Remote Similarity	NPC95090
0.6111	Remote Similarity	NPC27408
0.61	Remote Similarity	NPC479766
0.6044	Remote Similarity	NPC181712
0.5918	Remote Similarity	NPC22062
0.5918	Remote Similarity	NPC473634
0.5918	Remote Similarity	NPC138811
0.5851	Remote Similarity	NPC80188
0.5833	Remote Similarity	NPC488087
0.5794	Remote Similarity	NPC473644
0.5773	Remote Similarity	NPC8856
0.5741	Remote Similarity	NPC311850
0.5727	Remote Similarity	NPC68592
0.5688	Remote Similarity	NPC488083
0.56	Remote Similarity	NPC65003
0.5586	Remote Similarity	NPC488086
0.5577	Remote Similarity	NPC475382
0.5577	Remote Similarity	NPC479765
0.5545	Remote Similarity	NPC115674
0.5534	Remote Similarity	NPC473623
0.5534	Remote Similarity	NPC229409
0.5495	Remote Similarity	NPC488088
0.549	Remote Similarity	NPC64051
0.5481	Remote Similarity	NPC488089
0.5432	Remote Similarity	NPC29353
0.5429	Remote Similarity	NPC195257
0.5361	Remote Similarity	NPC22832
0.5361	Remote Similarity	NPC243930
0.5354	Remote Similarity	NPC600989
0.5312	Remote Similarity	NPC27942
0.5306	Remote Similarity	NPC220169
0.53	Remote Similarity	NPC606546
0.5258	Remote Similarity	NPC237435
0.5238	Remote Similarity	NPC209296
0.5213	Remote Similarity	NPC331652
0.5204	Remote Similarity	NPC43211
0.5169	Remote Similarity	NPC262222
0.5158	Remote Similarity	NPC39360
0.5158	Remote Similarity	NPC19709
0.5158	Remote Similarity	NPC29763
0.5158	Remote Similarity	NPC210003
0.5152	Remote Similarity	NPC607707
0.513	Remote Similarity	NPC298666
0.513	Remote Similarity	NPC198199
0.5128	Remote Similarity	NPC120952
0.5104	Remote Similarity	NPC189142
0.5104	Remote Similarity	NPC77660
0.5096	Remote Similarity	NPC122809
0.5053	Remote Similarity	NPC473043
0.5049	Remote Similarity	NPC44931

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC493109 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3984
0.1-0.2	5069
0.2-0.3	86
0.3-0.4	9
0.4-0.5	0
0.5-0.6	2
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
0.5258	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5238	Remote Similarity	NPD7054	Phase 4

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