NPASS Compound

Natural Product: NPC586071

Natural Product ID	NPC586071
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(4-hydroxyphenyl)-7-methoxy-5-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{S},4~{S},5~{S})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(4-hydroxyphenyl)-7-methoxy-5-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{S},4~{S},5~{S})-3,4,5-trihydroxytetrahydropyran-2-yl]oxymethyl]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 71 75 0 0 0 0 0 0 0 0999 V2000 -4.6474 -3.0957 3.3062 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3677 -3.0252 2.7214 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1477 -2.1670 1.6764 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8514 -2.1559 1.1512 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5536 -1.3236 0.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3340 -1.2111 -0.5038 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7852 -1.9344 -0.1427 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8198 -1.0874 0.3458 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8656 -1.9294 0.6762 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8305 -1.4238 1.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5068 -0.2789 1.3668 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7907 0.8614 1.1843 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0215 1.3104 -0.1228 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3730 1.1527 -0.3923 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1151 2.2274 0.3719 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2820 1.7725 0.9552 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2388 2.9059 1.3921 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0834 3.4969 2.3442 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3126 1.9700 2.0965 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9056 1.3426 3.1903 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6408 -2.3465 -0.5857 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8423 -3.7359 -0.5417 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6412 -2.1162 -1.7287 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4382 -0.7409 -1.8193 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3534 -2.7647 -1.2750 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5575 -4.0862 -0.8873 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5677 -0.4887 -0.4266 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2724 0.3497 -1.4794 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1237 0.3591 -1.9444 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2893 1.1672 -1.9897 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5234 1.0690 -1.3919 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6175 1.9118 -1.8999 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4887 2.7944 -2.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5931 3.5341 -3.3213 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7930 3.3709 -2.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9098 4.1008 -3.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9432 2.4824 -1.6251 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8489 1.7599 -1.2500 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7428 0.2464 -0.3869 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8295 -0.5365 0.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1506 -1.3804 1.1949 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7503 -3.9804 3.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3877 -3.1718 2.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8689 -2.1478 3.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0885 -2.7800 1.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6101 -2.6355 0.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3937 -2.8603 1.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6235 -2.2265 1.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3566 -1.3868 2.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7068 0.7346 1.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5473 1.2628 -1.4805 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7693 0.1817 -0.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4263 3.0243 -0.3654 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6929 1.0651 0.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6966 3.7421 0.9056 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6721 4.1876 1.9355 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4408 2.5263 2.4739 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7958 1.8801 4.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5613 -1.7803 -0.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6396 -3.9230 0.0260 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0150 -2.5503 -2.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8606 -0.5008 -2.5842 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6846 -2.7913 -2.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9303 -4.2791 -0.1532 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 1.8192 -2.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5408 2.9057 -3.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4918 4.2429 -4.1484 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0651 5.0327 -2.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8891 2.3453 -1.1031 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9615 1.0594 -0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1493 -1.3528 1.5587 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 1 0 6 7 1 0 7 8 1 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 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 9 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 5 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 31 39 1 0 39 40 1 0 40 41 2 0 41 3 1 0 25 7 1 0 40 27 1 0 19 12 1 0 38 32 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 7 46 1 1 9 47 1 1 10 48 1 0 10 49 1 0 12 50 1 6 14 51 1 0 14 52 1 0 15 53 1 6 16 54 1 0 17 55 1 6 18 56 1 0 19 57 1 1 20 58 1 0 21 59 1 6 22 60 1 0 23 61 1 6 24 62 1 0 25 63 1 6 26 64 1 0 30 65 1 0 33 66 1 0 34 67 1 0 36 68 1 0 37 69 1 0 38 70 1 0 41 71 1 0 M END

Standard InCHIKey	ZKIXACXWZQFVAB-ZTJOTJIESA-N
Standard InCHI	InChI=1S/C27H30O14/c1-36-13-6-17-20(14(29)8-16(39-17)11-2-4-12(28)5-3-11)18(7-13)40-27-25(35)23(33)22(32)19(41-27)10-38-26-24(34)21(31)15(30)9-37-26/h2-8,15,19,21-28,30-35H,9-10H2,1H3/t15-,19+,21-,22+,23-,24-,25+,26-,27+/m0/s1
SMILES	COC1=CC(O[C@@H]2O[C@H](CO[C@@H]3OC[C@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H](O)[C@H]2O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	0.952 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.412 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.575 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	217.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.176	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.545	Fsp³:	0.444
MCE-18:	112.41 ? 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:	0.641	Fluc inhibitor:	0.311 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.954 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.88 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.048	Promiscuous compounds:	0.244

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.368	MDCK Permeability:	-5.159
Pgp-inhibitor:	0.0	Pgp-substrate:	0.799
PAMPA:	0.997 ? 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):	0.842
20% Bioavailability (F20%):	0.838	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.388
Plasma Protein Binding (PPB):	78.084%	Volume Distribution (VD):	-0.154
Fu:	21.244% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.226
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.81
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.163 ? 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):

1.594

Half-life (T1/2):

3.225

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.077
Human Hepatotoxicity (H-HT):	0.623	Drug-induced Liver Injury (DILI):	0.963
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.101	Skin Sensitization:	0.999
Carcinogencity:	0.282	Eye Corrosion:	0.0
Eye Irritation:	0.455	Respiratory Toxicity:	0.029
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.889
Hematotoxicity:	0.417	Drug-induced Nephrotoxicity:	0.608
Genotoxicity:	0.957	RPMI-8226 Immunitoxicity:	0.179
A549 Cytotoxicity:	0.883	Hek293 Cytotoxicity:	0.864
BCF:	0.43 ? 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:	3.084 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.536 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.717 ? 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
NPO22809	Gnidia involucrata	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47865	Struthiola argentea	Genus	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22809	Gnidia involucrata	Species	Thymelaeaceae	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 NPC586071 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	22293
0.1-0.2	23726
0.2-0.3	2824
0.3-0.4	685
0.4-0.5	255
0.5-0.6	53
0.6-0.7	12
0.7-0.8	0
0.8-0.85	3
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	NPC129827
0.9487	High Similarity	NPC473512
0.875	High Similarity	NPC295613
0.8293	Intermediate Similarity	NPC473657
0.8193	Intermediate Similarity	NPC15358
0.8118	Intermediate Similarity	NPC284277
0.7701	Intermediate Similarity	NPC475497
0.6905	Remote Similarity	NPC610763
0.6593	Remote Similarity	NPC44931
0.6559	Remote Similarity	NPC475366
0.6484	Remote Similarity	NPC236191
0.6444	Remote Similarity	NPC52353
0.6413	Remote Similarity	NPC301683
0.6404	Remote Similarity	NPC293004
0.6304	Remote Similarity	NPC51774
0.6087	Remote Similarity	NPC172807
0.6	Remote Similarity	NPC22062
0.6	Remote Similarity	NPC473634
0.6	Remote Similarity	NPC138811
0.5957	Remote Similarity	NPC471079
0.59	Remote Similarity	NPC101636
0.5833	Remote Similarity	NPC210073
0.5773	Remote Similarity	NPC204693
0.5761	Remote Similarity	NPC284960
0.573	Remote Similarity	NPC110349
0.573	Remote Similarity	NPC83283
0.5729	Remote Similarity	NPC142996
0.5714	Remote Similarity	NPC182045
0.5714	Remote Similarity	NPC488074
0.5714	Remote Similarity	NPC64051
0.57	Remote Similarity	NPC488089
0.5657	Remote Similarity	NPC65711
0.56	Remote Similarity	NPC473623
0.56	Remote Similarity	NPC483707
0.56	Remote Similarity	NPC209296
0.5588	Remote Similarity	NPC298171
0.5567	Remote Similarity	NPC67326
0.5545	Remote Similarity	NPC270675
0.5545	Remote Similarity	NPC195685
0.5543	Remote Similarity	NPC27942
0.551	Remote Similarity	NPC102028
0.549	Remote Similarity	NPC231194
0.5474	Remote Similarity	NPC194483
0.5472	Remote Similarity	NPC472993
0.5455	Remote Similarity	NPC186816
0.5446	Remote Similarity	NPC51326
0.5444	Remote Similarity	NPC331652
0.5417	Remote Similarity	NPC211594
0.5385	Remote Similarity	NPC39360
0.5385	Remote Similarity	NPC29763
0.5385	Remote Similarity	NPC210003
0.5385	Remote Similarity	NPC472994
0.5361	Remote Similarity	NPC254540
0.5354	Remote Similarity	NPC245059
0.5333	Remote Similarity	NPC244875
0.5326	Remote Similarity	NPC93337
0.5312	Remote Similarity	NPC61791
0.53	Remote Similarity	NPC473571
0.53	Remote Similarity	NPC110941
0.5269	Remote Similarity	NPC105025
0.5248	Remote Similarity	NPC46202
0.5146	Remote Similarity	NPC229409
0.51	Remote Similarity	NPC173582
0.51	Remote Similarity	NPC265885
0.51	Remote Similarity	NPC181465
0.51	Remote Similarity	NPC215710
0.51	Remote Similarity	NPC67105
0.51	Remote Similarity	NPC473438
0.51	Remote Similarity	NPC253788
0.5096	Remote Similarity	NPC600130
0.505	Remote Similarity	NPC65563
0.505	Remote Similarity	NPC470949

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC586071 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5465
0.1-0.2	3612
0.2-0.3	60
0.3-0.4	8
0.4-0.5	3
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
0.6531	Remote Similarity	NPD7472	Pre-clinical
0.56	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