NPASS Compound

Natural Product: NPC324108

Natural Product ID	NPC324108
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DLIKSSGEMUFQOK-RINAGGJESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	25243883
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 53 56 0 0 0 0 0 0 0 0999 V2000 3.7595 1.8671 2.3483 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6263 2.0256 0.8710 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2562 1.9884 0.5158 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 1.0530 1.0249 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1385 0.8043 0.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7611 -0.1195 0.8881 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3738 -0.8055 2.0409 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 -0.5611 2.6469 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7353 0.3676 2.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0191 0.6346 2.7898 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4597 -0.1483 3.6603 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2361 -1.2421 3.8016 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9796 -0.3745 0.2902 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5466 0.1818 -0.8337 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7194 -0.8841 -1.8742 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7206 -1.8801 -1.3550 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9709 -1.1681 -0.9964 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8167 0.1239 -0.2928 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6972 0.8322 -0.4836 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0193 1.0429 -0.5581 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9340 2.0949 0.3380 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7826 -2.0765 -0.2754 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0170 -2.7507 -2.4271 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0532 -0.4052 -3.1156 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4453 1.0934 0.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3671 0.2975 0.7310 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1684 -0.6051 0.0192 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0087 -0.6785 -1.3563 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0888 0.1104 -2.0200 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3155 0.9925 -1.2675 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7966 -1.5721 -2.0922 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7593 1.9526 2.7506 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1804 2.7275 2.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9756 3.0650 0.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0878 1.3834 -0.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0503 -1.5290 2.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7951 -2.0764 3.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8640 0.9376 -1.2655 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7420 -1.4123 -1.9677 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3050 -2.5122 -0.5612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5528 -0.9790 -1.9443 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9013 -0.0977 0.8153 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9744 0.5173 -0.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0493 1.3650 -1.6150 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6861 2.9027 -0.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9425 -1.7236 0.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9649 -3.0077 -2.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5903 -1.0733 -3.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4966 0.3453 1.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8943 -1.2315 0.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9932 0.0243 -3.0959 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5988 1.6095 -1.7710 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7769 -1.4262 -2.2229 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 8 12 1 0 6 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 1 0 18 20 1 0 20 21 1 0 17 22 1 0 16 23 1 0 15 24 1 0 2 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 28 31 1 0 10 1 1 0 9 4 1 0 19 14 1 0 30 25 1 0 1 32 1 0 1 33 1 0 2 34 1 0 5 35 1 0 7 36 1 0 12 37 1 0 14 38 1 0 15 39 1 0 16 40 1 0 17 41 1 0 18 42 1 0 20 43 1 0 20 44 1 0 21 45 1 0 22 46 1 0 23 47 1 0 24 48 1 0 26 49 1 0 27 50 1 0 29 51 1 0 30 52 1 0 31 53 1 0 M END

Standard InCHIKey	DLIKSSGEMUFQOK-RINAGGJESA-N
Standard InCHI	InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,21?/m0/s1
SMILES	C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	434.12	Volume:	406.993 ? Van der Waals volume.
Dense:	1.067	LogP:	-0.017 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.752 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.888 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.385	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.002	Fsp³:	0.381
MCE-18:	87.069 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.278	Fluc inhibitor:	0.061 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.285 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.593 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.275	Promiscuous compounds:	0.21

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.421	MDCK Permeability:	-4.984
Pgp-inhibitor:	0.019	Pgp-substrate:	0.412
PAMPA:	0.989 ? 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):	0.428
20% Bioavailability (F20%):	0.022	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.806
Plasma Protein Binding (PPB):	81.258%	Volume Distribution (VD):	-0.084
Fu:	18.458% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.119
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.996
BSEP inhibitor:	0.503

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.579	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.625
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.028
HLM stability:	0.037 ? 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):

3.145

Half-life (T1/2):

2.552

ADMET: Toxicity

hERG Blockers:	0.101	hERG Blockers (10um):	0.448
Human Hepatotoxicity (H-HT):	0.719	Drug-induced Liver Injury (DILI):	0.631
AMES Toxicity:	0.728	Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.38	Skin Sensitization:	0.286
Carcinogencity:	0.365	Eye Corrosion:	0.0
Eye Irritation:	0.287	Respiratory Toxicity:	0.122
Drug-induced Neurotoxicity:	0.224	Ototoxicity:	0.942
Hematotoxicity:	0.091	Drug-induced Nephrotoxicity:	0.38
Genotoxicity:	0.62	RPMI-8226 Immunitoxicity:	0.097
A549 Cytotoxicity:	0.28	Hek293 Cytotoxicity:	0.848
BCF:	0.432 ? 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:	2.903 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.526 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.653 ? 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
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35268681]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38308284]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39410132]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31056	Mentha haplocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	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 NPC324108 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	17284
0.1-0.2	26787
0.2-0.3	4365
0.3-0.4	1090
0.4-0.5	249
0.5-0.6	49
0.6-0.7	16
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC39351
0.8615	High Similarity	NPC97052
0.8507	High Similarity	NPC29830
0.8485	Intermediate Similarity	NPC219163
0.8143	Intermediate Similarity	NPC236934
0.7571	Intermediate Similarity	NPC206378
0.7429	Intermediate Similarity	NPC26195
0.7391	Intermediate Similarity	NPC169248
0.7391	Intermediate Similarity	NPC72649
0.7179	Intermediate Similarity	NPC142860
0.7179	Intermediate Similarity	NPC152538
0.7179	Intermediate Similarity	NPC246469
0.7179	Intermediate Similarity	NPC89088
0.7051	Intermediate Similarity	NPC271270
0.7042	Intermediate Similarity	NPC170475
0.6986	Remote Similarity	NPC181014
0.6944	Remote Similarity	NPC471457
0.6709	Remote Similarity	NPC105283
0.6575	Remote Similarity	NPC163191
0.6517	Remote Similarity	NPC321916
0.64	Remote Similarity	NPC106625
0.625	Remote Similarity	NPC329203
0.625	Remote Similarity	NPC222342
0.6235	Remote Similarity	NPC168789
0.619	Remote Similarity	NPC291124
0.619	Remote Similarity	NPC131157
0.6164	Remote Similarity	NPC99233
0.6145	Remote Similarity	NPC97285
0.6133	Remote Similarity	NPC308265
0.6119	Remote Similarity	NPC23084
0.6071	Remote Similarity	NPC43587
0.5934	Remote Similarity	NPC318119
0.589	Remote Similarity	NPC121001
0.5875	Remote Similarity	NPC479540
0.5823	Remote Similarity	NPC5778
0.5747	Remote Similarity	NPC105095
0.5747	Remote Similarity	NPC177731
0.5747	Remote Similarity	NPC725
0.573	Remote Similarity	NPC67134
0.5714	Remote Similarity	NPC45400
0.5714	Remote Similarity	NPC259182
0.5714	Remote Similarity	NPC603902
0.5632	Remote Similarity	NPC44328
0.5632	Remote Similarity	NPC79056
0.5625	Remote Similarity	NPC300537
0.5568	Remote Similarity	NPC293629
0.5556	Remote Similarity	NPC472381
0.5556	Remote Similarity	NPC472383
0.5526	Remote Similarity	NPC57587
0.5479	Remote Similarity	NPC199335
0.5444	Remote Similarity	NPC47140
0.5422	Remote Similarity	NPC259834
0.5405	Remote Similarity	NPC190217
0.5385	Remote Similarity	NPC261254
0.5375	Remote Similarity	NPC149244
0.5375	Remote Similarity	NPC225445
0.5316	Remote Similarity	NPC88484
0.5312	Remote Similarity	NPC483821
0.5312	Remote Similarity	NPC142319
0.527	Remote Similarity	NPC477240
0.5224	Remote Similarity	NPC32441
0.5224	Remote Similarity	NPC6407
0.5224	Remote Similarity	NPC79943
0.5224	Remote Similarity	NPC545184
0.5217	Remote Similarity	NPC214454
0.519	Remote Similarity	NPC271479
0.5185	Remote Similarity	NPC472353
0.5185	Remote Similarity	NPC257963
0.5181	Remote Similarity	NPC477502
0.5152	Remote Similarity	NPC483820
0.5147	Remote Similarity	NPC150648
0.5139	Remote Similarity	NPC214910
0.5132	Remote Similarity	NPC479374
0.5104	Remote Similarity	NPC241196
0.5072	Remote Similarity	NPC73028
0.5072	Remote Similarity	NPC145900
0.5065	Remote Similarity	NPC604892
0.5063	Remote Similarity	NPC148273
0.506	Remote Similarity	NPC472320
0.5056	Remote Similarity	NPC472876

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC324108 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4328
0.1-0.2	4696
0.2-0.3	103
0.3-0.4	18
0.4-0.5	3
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
0.5632	Remote Similarity	NPD7074	Phase 3
0.5224	Remote Similarity	NPD1552	Clinical (unspecified phase)

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