NPASS Compound

Natural Product: NPC165256

Natural Product ID	NPC165256
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZTIZEXUIEBLYBL-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	53395135
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 72 76 0 0 0 0 0 0 0 0999 V2000 -10.1715 -0.7771 -0.8648 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3958 -0.3916 0.2489 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0180 -0.3392 0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4072 -0.6646 -1.0882 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0375 -0.5914 -1.1403 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2410 -0.2173 -0.0688 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9169 0.0909 1.1017 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2735 0.0372 1.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9257 0.3480 2.3896 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1491 0.7345 3.5057 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7855 -0.1651 -0.1990 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0861 0.4741 0.9587 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4631 -0.5196 1.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3317 -1.0219 1.3118 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0460 -0.2801 0.1657 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3915 -0.1705 -0.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3263 -0.0228 0.9307 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6748 0.0744 0.6067 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1476 0.0304 -0.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1860 -0.1210 -1.6924 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8598 -0.2159 -1.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0746 -0.3674 -2.3987 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3638 -0.4173 -3.7331 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4865 0.1253 -1.0271 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5575 0.2773 -0.1651 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4421 1.4647 -0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8420 1.2480 -0.0582 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9560 0.2648 1.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1127 -0.9679 0.8455 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9231 -2.2269 0.7635 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8058 -2.2247 -0.2988 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3874 -0.8574 -0.3455 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5493 0.9207 2.2449 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7016 0.8553 -1.0872 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4492 1.5541 -1.9282 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8151 0.9820 0.2407 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4522 1.4448 -1.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3416 0.4254 -1.3578 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9546 -0.1213 -1.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2409 -0.6841 -0.6454 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8778 -1.8010 -1.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9997 -0.9601 -1.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5745 -0.8478 -2.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3501 0.3868 1.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8022 0.9484 4.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5933 1.6571 3.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3949 -0.0604 3.7447 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4302 -1.2381 -0.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6153 1.2958 1.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1889 -1.2947 2.2135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1613 0.0346 2.8177 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4775 -0.8912 -0.6791 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9709 0.0135 1.9482 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3761 0.1906 1.4330 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5240 -0.1590 -2.7145 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4738 -0.3347 -4.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9767 -1.3228 -3.8964 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0455 0.4480 -3.9788 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2949 0.3404 0.9052 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0134 2.4134 -0.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2380 2.2254 0.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0284 0.0072 1.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3705 -1.0721 1.6601 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4484 -2.4515 1.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2091 -3.0642 0.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3296 -2.6018 -1.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8968 0.3598 2.7226 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3233 1.0854 -1.9845 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0804 0.7351 -2.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3365 1.7881 0.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7697 1.7045 -1.8397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1152 2.3154 -0.7424 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 6 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 19 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 15 36 1 0 36 37 1 0 37 38 1 0 8 3 1 0 38 11 1 0 36 12 1 0 21 16 1 0 32 25 1 0 1 39 1 0 1 40 1 0 1 41 1 0 4 42 1 0 5 43 1 0 7 44 1 0 10 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 15 52 1 0 17 53 1 0 18 54 1 0 20 55 1 0 23 56 1 0 23 57 1 0 23 58 1 0 25 59 1 0 26 60 1 0 27 61 1 0 28 62 1 0 29 63 1 0 30 64 1 0 30 65 1 0 31 66 1 0 33 67 1 0 34 68 1 0 35 69 1 0 36 70 1 0 37 71 1 0 37 72 1 0 M END

Standard InCHIKey	ZTIZEXUIEBLYBL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C27H34O11/c1-32-18-7-4-13(8-20(18)34-3)25-16-11-36-26(17(16)12-35-25)15-6-5-14(9-19(15)33-2)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,16-17,21-31H,10-12H2,1-3H3
SMILES	COc1ccc(cc1OC)C1C2COC(c3ccc(cc3OC)OC3C(C(C(C(CO)O3)O)O)O)C2CO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.21	Volume:	513.64 ? Van der Waals volume.
Dense:	1.04	LogP:	0.123 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.846 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.883 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	27.0
TPSA:	145.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.384	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.429	Fsp³:	0.556
MCE-18:	105.714 ? 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:	0.043	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.39 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.145	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.835	MDCK Permeability:	-5.208
Pgp-inhibitor:	0.0	Pgp-substrate:	0.144
PAMPA:	0.153 ? 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):	0.875
20% Bioavailability (F20%):	0.128	30% Bioavailability (F30%):	0.506
50% Bioavailability (F50%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.939
Plasma Protein Binding (PPB):	69.079%	Volume Distribution (VD):	-0.35
Fu:	30.239% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.101
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.625
BSEP inhibitor:	0.876

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.986	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.975	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.507	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.0
HLM stability:	0.003 ? 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):

2.824

Half-life (T1/2):

3.24

ADMET: Toxicity

hERG Blockers:	0.15	hERG Blockers (10um):	0.427
Human Hepatotoxicity (H-HT):	0.637	Drug-induced Liver Injury (DILI):	0.885
AMES Toxicity:	0.725	Rat Oral Acute Toxicity:	0.332
Maximum Recommended Daily Dose:	0.255	Skin Sensitization:	0.063
Carcinogencity:	0.277	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.14
Drug-induced Neurotoxicity:	0.503	Ototoxicity:	0.961
Hematotoxicity:	0.133	Drug-induced Nephrotoxicity:	0.165
Genotoxicity:	0.272	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.049	Hek293 Cytotoxicity:	0.449
BCF:	0.971 ? 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:	3.507 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.585 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.32 ? 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
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17156960]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422318]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28218000]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2681	Phillyrea latifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2681	Phillyrea latifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2681	Phillyrea latifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21387	Forsythia suspensa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2681	Phillyrea latifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21387	Forsythia suspensa	Species	Oleaceae	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 NPC165256 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	18994
0.1-0.2	26900
0.2-0.3	3095
0.3-0.4	643
0.4-0.5	174
0.5-0.6	28
0.6-0.7	20
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC246947
0.7846	Intermediate Similarity	NPC276753
0.7846	Intermediate Similarity	NPC205796
0.6986	Remote Similarity	NPC286235
0.6892	Remote Similarity	NPC38041
0.6892	Remote Similarity	NPC22150
0.6892	Remote Similarity	NPC279298
0.6866	Remote Similarity	NPC95392
0.6866	Remote Similarity	NPC84013
0.6866	Remote Similarity	NPC55715
0.6866	Remote Similarity	NPC35877
0.6795	Remote Similarity	NPC486098
0.6575	Remote Similarity	NPC486104
0.6386	Remote Similarity	NPC486097
0.6316	Remote Similarity	NPC51328
0.6316	Remote Similarity	NPC55158
0.625	Remote Similarity	NPC486107
0.6216	Remote Similarity	NPC216129
0.6216	Remote Similarity	NPC130449
0.6216	Remote Similarity	NPC248132
0.6133	Remote Similarity	NPC486102
0.6076	Remote Similarity	NPC486100
0.6076	Remote Similarity	NPC486101
0.5976	Remote Similarity	NPC186316
0.5949	Remote Similarity	NPC471063
0.5833	Remote Similarity	NPC478055
0.5647	Remote Similarity	NPC486099
0.5556	Remote Similarity	NPC486109
0.5556	Remote Similarity	NPC486108
0.5556	Remote Similarity	NPC486106
0.5488	Remote Similarity	NPC486105
0.5465	Remote Similarity	NPC185307
0.5455	Remote Similarity	NPC153149
0.5402	Remote Similarity	NPC112861
0.5278	Remote Similarity	NPC479028
0.5278	Remote Similarity	NPC479031
0.525	Remote Similarity	NPC108674
0.5244	Remote Similarity	NPC18979
0.5227	Remote Similarity	NPC470235
0.5195	Remote Similarity	NPC479030
0.5172	Remote Similarity	NPC486103
0.5165	Remote Similarity	NPC11411
0.5147	Remote Similarity	NPC25817
0.5139	Remote Similarity	NPC218685
0.5135	Remote Similarity	NPC479029
0.5114	Remote Similarity	NPC470950
0.5079	Remote Similarity	NPC121783
0.5079	Remote Similarity	NPC34902
0.5079	Remote Similarity	NPC18449
0.507	Remote Similarity	NPC166040
0.5057	Remote Similarity	NPC39657

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4764
0.1-0.2	4225
0.2-0.3	152
0.3-0.4	8
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