NPASS Compound

Natural Product: NPC580995

Natural Product ID	NPC580995
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-2-(4-methoxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-2-(4-methoxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
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 55 58 0 0 0 0 0 0 0 0999 V2000 3.6302 -4.7769 2.7169 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7184 -4.6097 1.6362 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4703 -3.3129 1.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6009 -3.1007 0.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3597 -1.7918 -0.2719 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9475 -0.6919 0.2878 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 0.6978 -0.0914 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6221 1.0761 -0.8253 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3593 0.2608 -1.2972 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5855 0.0435 -0.6146 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8012 -1.3032 -0.4558 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9192 -1.5265 0.3717 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1224 -2.9995 0.5368 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3464 -3.6583 -0.6673 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1157 -0.7800 -0.1163 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3053 -1.4752 -0.0022 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8235 -0.3541 -1.5479 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3709 -1.4253 -2.3159 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7155 0.6773 -1.4578 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2496 1.7725 -0.7787 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5011 2.4291 -1.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4576 2.8344 -1.7935 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4188 3.3518 -0.6875 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2526 4.6862 -1.0065 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1374 5.0696 -1.7755 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1719 5.5924 -0.5679 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2439 5.1469 0.1837 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1775 6.0925 0.6250 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4092 3.8150 0.5017 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4743 2.8776 0.0582 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5917 1.6125 0.3345 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8225 -0.9406 1.3343 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0697 -2.2081 1.7676 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8047 -5.8701 2.8581 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2516 -4.3383 3.6595 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6058 -4.3157 2.4877 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1104 -3.9336 -0.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6981 -1.6796 -1.1124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5950 0.5174 0.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6055 -1.1338 1.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2150 -3.4206 1.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9627 -3.2233 1.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1726 -4.6396 -0.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2124 0.1803 0.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6345 -1.6797 -0.9305 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7253 0.0820 -2.0184 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1486 -1.9441 -2.6610 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3275 0.9462 -2.4648 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1407 2.6224 -1.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7759 5.2123 -1.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0255 6.6352 -0.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5798 5.9728 1.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2339 3.4431 1.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3043 -0.1027 1.7994 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7635 -2.4114 2.5979 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 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 8 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 24 26 1 0 26 27 2 0 27 28 1 0 27 29 1 0 29 30 2 0 30 31 1 0 6 32 1 0 32 33 2 0 33 3 1 0 31 7 1 0 19 10 1 0 30 23 1 0 1 34 1 0 1 35 1 0 1 36 1 0 4 37 1 0 5 38 1 0 10 39 1 1 12 40 1 1 13 41 1 0 13 42 1 0 14 43 1 0 15 44 1 1 16 45 1 0 17 46 1 6 18 47 1 0 19 48 1 6 20 49 1 0 25 50 1 0 26 51 1 0 28 52 1 0 29 53 1 0 32 54 1 0 33 55 1 0 M END

Standard InCHIKey	MQVRGDZCYDEQML-UVHBULKNSA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-11-4-2-9(3-5-11)20-21(17(27)15-12(25)6-10(24)7-13(15)31-20)33-22-19(29)18(28)16(26)14(8-23)32-22/h2-7,14,16,18-19,22-26,28-29H,8H2,1H3/t14-,16+,18+,19-,22+/m1/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.12	Volume:	430.443 ? Van der Waals volume.
Dense:	1.074	LogP:	1.488 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.801 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.287 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	179.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.302	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.812	Fsp³:	0.318
MCE-18:	86.966 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.597	Fluc inhibitor:	0.372 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.854 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.814 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.11	Promiscuous compounds:	0.589

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.201	MDCK Permeability:	-5.256
Pgp-inhibitor:	0.0	Pgp-substrate:	0.544
PAMPA:	0.919 ? 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):	0.909
20% Bioavailability (F20%):	0.655	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.467
Plasma Protein Binding (PPB):	91.976%	Volume Distribution (VD):	-0.028
Fu:	7.475% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.799
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.396
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.155	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.006	CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.981 ? 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):

2.33

Half-life (T1/2):

2.133

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.153
Human Hepatotoxicity (H-HT):	0.663	Drug-induced Liver Injury (DILI):	0.958
AMES Toxicity:	0.946	Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.218	Skin Sensitization:	0.998
Carcinogencity:	0.532	Eye Corrosion:	0.001
Eye Irritation:	0.867	Respiratory Toxicity:	0.238
Drug-induced Neurotoxicity:	0.036	Ototoxicity:	0.569
Hematotoxicity:	0.306	Drug-induced Nephrotoxicity:	0.309
Genotoxicity:	0.943	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.776	Hek293 Cytotoxicity:	0.769
BCF:	0.506 ? 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:	3.281 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.709 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.895 ? 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
NPO29231	Prosopis juliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29231	Prosopis juliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29231	Prosopis juliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29231	Prosopis juliflora	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 NPC580995 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	18605
0.1-0.2	26828
0.2-0.3	2921
0.3-0.4	890
0.4-0.5	292
0.5-0.6	69
0.6-0.7	93
0.7-0.8	0
0.8-0.85	17
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472459
0.9412	High Similarity	NPC64305
0.863	High Similarity	NPC120099
0.8451	Intermediate Similarity	NPC77672
0.8451	Intermediate Similarity	NPC133671
0.8451	Intermediate Similarity	NPC135391
0.8451	Intermediate Similarity	NPC78263
0.8451	Intermediate Similarity	NPC250069
0.8243	Intermediate Similarity	NPC60735
0.8243	Intermediate Similarity	NPC26230
0.8133	Intermediate Similarity	NPC609478
0.8108	Intermediate Similarity	NPC325555
0.8108	Intermediate Similarity	NPC226304
0.8082	Intermediate Similarity	NPC145038
0.8082	Intermediate Similarity	NPC56077
0.8082	Intermediate Similarity	NPC281131
0.8082	Intermediate Similarity	NPC253662
0.8082	Intermediate Similarity	NPC179950
0.8082	Intermediate Similarity	NPC88789
0.8082	Intermediate Similarity	NPC491374
0.7945	Intermediate Similarity	NPC19388
0.7945	Intermediate Similarity	NPC240431
0.7945	Intermediate Similarity	NPC55786
0.7922	Intermediate Similarity	NPC203050
0.7922	Intermediate Similarity	NPC225434
0.7534	Intermediate Similarity	NPC288084
0.7467	Intermediate Similarity	NPC289667
0.7326	Intermediate Similarity	NPC76831
0.7308	Intermediate Similarity	NPC219904
0.7237	Intermediate Similarity	NPC143851
0.72	Intermediate Similarity	NPC67037
0.72	Intermediate Similarity	NPC255615
0.7105	Intermediate Similarity	NPC111929
0.7105	Intermediate Similarity	NPC320283
0.7105	Intermediate Similarity	NPC41121
0.7067	Intermediate Similarity	NPC34531
0.7051	Intermediate Similarity	NPC488080
0.7051	Intermediate Similarity	NPC169977
0.6988	Remote Similarity	NPC139320
0.6923	Remote Similarity	NPC297987
0.6923	Remote Similarity	NPC265530
0.6875	Remote Similarity	NPC175107
0.6829	Remote Similarity	NPC170052
0.6829	Remote Similarity	NPC135846
0.6824	Remote Similarity	NPC156869
0.6795	Remote Similarity	NPC127546
0.6795	Remote Similarity	NPC57625
0.6795	Remote Similarity	NPC173637
0.6795	Remote Similarity	NPC317489
0.6795	Remote Similarity	NPC223424
0.6795	Remote Similarity	NPC600591
0.6786	Remote Similarity	NPC29958
0.6774	Remote Similarity	NPC470712
0.6771	Remote Similarity	NPC470713
0.675	Remote Similarity	NPC42773
0.675	Remote Similarity	NPC21100
0.675	Remote Similarity	NPC45522
0.6707	Remote Similarity	NPC223747
0.6707	Remote Similarity	NPC88023
0.6707	Remote Similarity	NPC309025
0.6706	Remote Similarity	NPC471748
0.6667	Remote Similarity	NPC48984
0.6667	Remote Similarity	NPC191306
0.6667	Remote Similarity	NPC135599
0.6667	Remote Similarity	NPC73855
0.6667	Remote Similarity	NPC113968
0.6667	Remote Similarity	NPC328940
0.6667	Remote Similarity	NPC277174
0.6667	Remote Similarity	NPC606877
0.6625	Remote Similarity	NPC24043
0.6618	Remote Similarity	NPC59951
0.6548	Remote Similarity	NPC254855
0.6548	Remote Similarity	NPC94610
0.6543	Remote Similarity	NPC599850
0.6512	Remote Similarity	NPC470405
0.6506	Remote Similarity	NPC116458
0.6506	Remote Similarity	NPC246943
0.65	Remote Similarity	NPC8573
0.65	Remote Similarity	NPC136042
0.642	Remote Similarity	NPC84362
0.6395	Remote Similarity	NPC609888
0.6386	Remote Similarity	NPC101026
0.6386	Remote Similarity	NPC488077
0.6386	Remote Similarity	NPC224530
0.6353	Remote Similarity	NPC116864
0.6353	Remote Similarity	NPC244776
0.6333	Remote Similarity	NPC473327
0.6322	Remote Similarity	NPC163242
0.6322	Remote Similarity	NPC272068
0.6296	Remote Similarity	NPC156457
0.6292	Remote Similarity	NPC153755
0.6282	Remote Similarity	NPC54802
0.6282	Remote Similarity	NPC197304
0.6279	Remote Similarity	NPC251417
0.6265	Remote Similarity	NPC159579
0.6265	Remote Similarity	NPC488071
0.6211	Remote Similarity	NPC189564
0.6207	Remote Similarity	NPC471079
0.619	Remote Similarity	NPC148710
0.619	Remote Similarity	NPC21666
0.618	Remote Similarity	NPC129264
0.6146	Remote Similarity	NPC219043
0.6145	Remote Similarity	NPC138540
0.6136	Remote Similarity	NPC173582
0.6136	Remote Similarity	NPC265885
0.6136	Remote Similarity	NPC181465
0.6136	Remote Similarity	NPC215710
0.6136	Remote Similarity	NPC473438
0.6136	Remote Similarity	NPC253788
0.6122	Remote Similarity	NPC470718
0.6118	Remote Similarity	NPC206123
0.6118	Remote Similarity	NPC209023
0.6118	Remote Similarity	NPC605784
0.6111	Remote Similarity	NPC64425
0.6104	Remote Similarity	NPC78697
0.6098	Remote Similarity	NPC95090
0.6098	Remote Similarity	NPC27408
0.6087	Remote Similarity	NPC5319
0.6067	Remote Similarity	NPC155877
0.6067	Remote Similarity	NPC304741
0.6067	Remote Similarity	NPC605592
0.6049	Remote Similarity	NPC476771
0.6024	Remote Similarity	NPC46420
0.6022	Remote Similarity	NPC220173
0.602	Remote Similarity	NPC277532
0.6	Remote Similarity	NPC276222
0.6	Remote Similarity	NPC274618
0.6	Remote Similarity	NPC197285
0.6	Remote Similarity	NPC118284
0.6	Remote Similarity	NPC601710
0.6	Remote Similarity	NPC608147
0.5979	Remote Similarity	NPC292019
0.5979	Remote Similarity	NPC202908
0.5978	Remote Similarity	NPC270448
0.5976	Remote Similarity	NPC254306
0.5957	Remote Similarity	NPC292929
0.5955	Remote Similarity	NPC67326
0.5938	Remote Similarity	NPC203145
0.5934	Remote Similarity	NPC470125
0.593	Remote Similarity	NPC136761
0.5909	Remote Similarity	NPC278419
0.5909	Remote Similarity	NPC179198
0.5895	Remote Similarity	NPC602448
0.5889	Remote Similarity	NPC203259
0.5889	Remote Similarity	NPC33054
0.5889	Remote Similarity	NPC176740
0.5889	Remote Similarity	NPC471725
0.5889	Remote Similarity	NPC134532
0.5889	Remote Similarity	NPC602582
0.5882	Remote Similarity	NPC182121
0.5882	Remote Similarity	NPC611303
0.5862	Remote Similarity	NPC488072
0.5862	Remote Similarity	NPC476215
0.5851	Remote Similarity	NPC476472
0.5851	Remote Similarity	NPC294815
0.5851	Remote Similarity	NPC85751
0.5851	Remote Similarity	NPC16194
0.5851	Remote Similarity	NPC19240
0.5833	Remote Similarity	NPC186807
0.5824	Remote Similarity	NPC255157
0.5824	Remote Similarity	NPC259896
0.5816	Remote Similarity	NPC477895
0.5814	Remote Similarity	NPC486578
0.5806	Remote Similarity	NPC37668
0.58	Remote Similarity	NPC279473
0.5783	Remote Similarity	NPC58053
0.5783	Remote Similarity	NPC249281
0.5778	Remote Similarity	NPC39834
0.5765	Remote Similarity	NPC216496
0.5761	Remote Similarity	NPC61904
0.5761	Remote Similarity	NPC488073
0.5698	Remote Similarity	NPC168584
0.5698	Remote Similarity	NPC481043
0.5698	Remote Similarity	NPC129217
0.5673	Remote Similarity	NPC470720
0.567	Remote Similarity	NPC214621
0.567	Remote Similarity	NPC34267
0.5667	Remote Similarity	NPC480466
0.5647	Remote Similarity	NPC305811
0.5647	Remote Similarity	NPC52550
0.5647	Remote Similarity	NPC271692
0.5647	Remote Similarity	NPC603655
0.5644	Remote Similarity	NPC470716
0.5638	Remote Similarity	NPC35119
0.5632	Remote Similarity	NPC22832
0.5632	Remote Similarity	NPC85707
0.5625	Remote Similarity	NPC287889
0.5618	Remote Similarity	NPC95866
0.56	Remote Similarity	NPC217520
0.56	Remote Similarity	NPC470715
0.5595	Remote Similarity	NPC112755
0.5595	Remote Similarity	NPC170675
0.5595	Remote Similarity	NPC476772
0.5591	Remote Similarity	NPC253521
0.5591	Remote Similarity	NPC296018
0.5591	Remote Similarity	NPC113836
0.5579	Remote Similarity	NPC205824
0.5567	Remote Similarity	NPC223426
0.5566	Remote Similarity	NPC192539
0.5556	Remote Similarity	NPC480463

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC580995 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4915
0.1-0.2	4122
0.2-0.3	93
0.3-0.4	13
0.4-0.5	5
0.5-0.6	1
0.6-0.7	1
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
0.6087	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6797	Phase 2

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