NPASS Compound

Natural Product: NPC581172

Natural Product ID	NPC581172
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dihydroxyphenyl)-5-hydroxy-3-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-hydroxy-3-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-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 77 81 0 0 0 0 0 0 0 0999 V2000 -8.8369 -1.5562 0.3743 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9391 -1.0438 1.3757 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6227 -0.8553 1.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1587 0.3131 0.5318 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9596 1.5152 0.3599 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4153 2.5883 -0.3758 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0816 3.7708 -0.5520 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3265 3.9868 -0.0214 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9793 5.1923 -0.2149 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8791 2.9623 0.6982 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1288 3.1162 1.2580 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1957 1.7465 0.8811 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8619 0.3831 0.1897 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0300 -0.6203 0.2939 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7134 -0.4878 -0.0722 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7665 -1.5193 0.0127 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4714 -1.2925 -0.3773 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5363 -2.2217 -0.3383 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6217 -1.8397 0.4598 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7671 -1.5560 -0.2384 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7269 -0.8220 0.6715 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8954 -0.5277 -0.0171 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8028 0.1459 0.7816 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0972 1.3689 0.1931 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1530 2.0222 0.8042 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3527 3.3383 0.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4173 4.0598 0.6543 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4357 1.2646 0.7908 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0271 1.1670 2.0485 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2315 -0.1256 0.2131 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1385 -0.0824 -1.1666 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0398 -0.7366 0.8748 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3203 -0.9218 2.2235 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3877 -0.5479 -1.3323 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5066 0.1373 -1.7849 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6836 -1.3223 -2.3940 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8398 -0.5417 -3.1724 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.4824 -1.7741 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6612 -3.6694 -1.8508 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2301 -2.7171 0.4972 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5599 -2.8615 0.8702 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0110 -4.0863 1.3600 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4651 -1.8471 0.7803 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7793 -1.9598 1.1386 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1978 -3.0612 1.5820 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8800 -1.1820 0.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4750 -1.2421 -0.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8292 -2.6629 0.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4324 2.4493 -0.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6252 4.5784 -1.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8550 5.1636 -0.7368 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9024 3.3139 0.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6702 0.9843 1.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3720 0.4764 -0.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2291 -3.2101 0.0480 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2556 -2.4008 -0.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3197 0.1194 1.0504 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9845 -1.4522 1.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3339 0.2725 1.7820 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8513 2.2995 1.8570 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6000 3.1237 -0.9990 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4116 3.9077 0.0839 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0769 4.9797 0.7840 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1771 1.7632 0.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3791 1.0887 2.7822 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1174 -0.7206 0.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2894 -0.5510 -1.4235 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8701 -1.7424 0.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7696 -1.8076 2.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6318 0.1583 -0.8834 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3884 1.0938 -1.5474 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4759 -1.7360 -3.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9929 0.4007 -2.9330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0152 -2.6150 -2.3450 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5317 -4.1839 -1.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5750 -3.5831 0.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0926 -4.8566 0.7348 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 8 10 1 0 10 11 1 0 10 12 2 0 4 13 1 0 13 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 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 20 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 16 40 2 0 40 41 1 0 41 42 1 0 41 43 2 0 43 44 1 0 44 45 2 0 44 3 1 0 12 5 1 0 43 14 1 0 38 18 1 0 32 23 1 0 1 46 1 0 1 47 1 0 1 48 1 0 6 49 1 0 7 50 1 0 9 51 1 0 11 52 1 0 12 53 1 0 15 54 1 0 18 55 1 1 20 56 1 6 21 57 1 0 21 58 1 0 23 59 1 1 25 60 1 1 26 61 1 0 26 62 1 0 27 63 1 0 28 64 1 6 29 65 1 0 30 66 1 6 31 67 1 0 32 68 1 6 33 69 1 0 34 70 1 1 35 71 1 0 36 72 1 6 37 73 1 0 38 74 1 6 39 75 1 0 40 76 1 0 42 77 1 0 M END

Standard InCHIKey	CWHCBJYWFQQIOT-GZKNRDGBSA-N
Standard InCHI	InChI=1S/C28H32O17/c1-40-26-20(35)17-13(32)5-10(6-14(17)43-25(26)9-2-3-11(30)12(31)4-9)42-28-24(39)22(37)19(34)16(45-28)8-41-27-23(38)21(36)18(33)15(7-29)44-27/h2-6,15-16,18-19,21-24,27-34,36-39H,7-8H2,1H3/t15-,16-,18-,19-,21+,22+,23-,24-,27-,28-/m1/s1
SMILES	COC1=C(C2=CC=C(O)C(O)=C2)OC2=CC(O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	640.16	Volume:	578.404 ? Van der Waals volume.
Dense:	1.107	LogP:	-0.025 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.861 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.603 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	278.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.115	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.788	Fsp³:	0.464
MCE-18:	122.073 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.615	Fluc inhibitor:	0.278 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.927 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.624 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.535

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.538	MDCK Permeability:	-5.17
Pgp-inhibitor:	0.0	Pgp-substrate:	0.299
PAMPA:	0.996 ? 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):	0.991
20% Bioavailability (F20%):	0.309	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.15
Plasma Protein Binding (PPB):	78.65%	Volume Distribution (VD):	-0.208
Fu:	20.228% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.21
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	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:	0.754
HLM stability:	0.026 ? 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):

1.921

Half-life (T1/2):

4.964

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.055
Human Hepatotoxicity (H-HT):	0.45	Drug-induced Liver Injury (DILI):	0.983
AMES Toxicity:	0.953	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.01	Skin Sensitization:	0.999
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.06	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.99
Hematotoxicity:	0.084	Drug-induced Nephrotoxicity:	0.353
Genotoxicity:	0.877	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.776	Hek293 Cytotoxicity:	0.311
BCF:	0.442 ? 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:	2.966 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.586 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.66 ? 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
NPO50319	Lonicera implexa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC581172 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	23218
0.1-0.2	22133
0.2-0.3	3218
0.3-0.4	724
0.4-0.5	287
0.5-0.6	122
0.6-0.7	67
0.7-0.8	1
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
0.8333	Intermediate Similarity	NPC84362
0.775	Intermediate Similarity	NPC136042
0.766	Intermediate Similarity	NPC480441
0.7614	Intermediate Similarity	NPC488073
0.7586	Intermediate Similarity	NPC156869
0.7303	Intermediate Similarity	NPC186816
0.7294	Intermediate Similarity	NPC605784
0.7273	Intermediate Similarity	NPC275454
0.7079	Intermediate Similarity	NPC67105
0.7024	Intermediate Similarity	NPC271692
0.7	Intermediate Similarity	NPC210073
0.6957	Remote Similarity	NPC470443
0.6939	Remote Similarity	NPC25523
0.6905	Remote Similarity	NPC297987
0.6875	Remote Similarity	NPC14187
0.6809	Remote Similarity	NPC486577
0.6706	Remote Similarity	NPC277205
0.6706	Remote Similarity	NPC37919
0.6667	Remote Similarity	NPC126784
0.6667	Remote Similarity	NPC241423
0.663	Remote Similarity	NPC203259
0.663	Remote Similarity	NPC33054
0.663	Remote Similarity	NPC176740
0.663	Remote Similarity	NPC471725
0.663	Remote Similarity	NPC134532
0.663	Remote Similarity	NPC602582
0.6596	Remote Similarity	NPC65711
0.6588	Remote Similarity	NPC289667
0.6522	Remote Similarity	NPC67326
0.6517	Remote Similarity	NPC116458
0.6517	Remote Similarity	NPC246943
0.6512	Remote Similarity	NPC189142
0.6512	Remote Similarity	NPC77660
0.65	Remote Similarity	NPC292019
0.65	Remote Similarity	NPC202908
0.6489	Remote Similarity	NPC488074
0.6477	Remote Similarity	NPC488071
0.6392	Remote Similarity	NPC473073
0.6344	Remote Similarity	NPC44931
0.6344	Remote Similarity	NPC227508
0.6289	Remote Similarity	NPC142142
0.6277	Remote Similarity	NPC22062
0.6277	Remote Similarity	NPC479405
0.6277	Remote Similarity	NPC473634
0.6277	Remote Similarity	NPC138811
0.625	Remote Similarity	NPC46420
0.6214	Remote Similarity	NPC277532
0.6211	Remote Similarity	NPC479404
0.6186	Remote Similarity	NPC209296
0.6186	Remote Similarity	NPC35119
0.618	Remote Similarity	NPC42773
0.618	Remote Similarity	NPC45522
0.6146	Remote Similarity	NPC64425
0.6139	Remote Similarity	NPC121703
0.6136	Remote Similarity	NPC145038
0.6136	Remote Similarity	NPC56077
0.6136	Remote Similarity	NPC281131
0.6136	Remote Similarity	NPC253662
0.6136	Remote Similarity	NPC179950
0.6136	Remote Similarity	NPC158674
0.6136	Remote Similarity	NPC88789
0.6136	Remote Similarity	NPC491374
0.6129	Remote Similarity	NPC251417
0.61	Remote Similarity	NPC470446
0.61	Remote Similarity	NPC135358
0.6082	Remote Similarity	NPC479403
0.6023	Remote Similarity	NPC249281
0.6022	Remote Similarity	NPC116864
0.6022	Remote Similarity	NPC244776
0.602	Remote Similarity	NPC32641
0.602	Remote Similarity	NPC256188
0.6	Remote Similarity	NPC173582
0.6	Remote Similarity	NPC265885
0.6	Remote Similarity	NPC181465
0.6	Remote Similarity	NPC215710
0.6	Remote Similarity	NPC473438
0.6	Remote Similarity	NPC253788
0.6	Remote Similarity	NPC599850
0.5979	Remote Similarity	NPC240306
0.5974	Remote Similarity	NPC188871
0.5955	Remote Similarity	NPC323593
0.5955	Remote Similarity	NPC203500
0.5934	Remote Similarity	NPC611303
0.5922	Remote Similarity	NPC189564
0.5914	Remote Similarity	NPC276377
0.59	Remote Similarity	NPC476472
0.59	Remote Similarity	NPC294815
0.59	Remote Similarity	NPC16194
0.5895	Remote Similarity	NPC480466
0.5895	Remote Similarity	NPC471079
0.5876	Remote Similarity	NPC473571
0.5876	Remote Similarity	NPC110941
0.5872	Remote Similarity	NPC488078
0.5859	Remote Similarity	NPC473623
0.5859	Remote Similarity	NPC229409
0.5859	Remote Similarity	NPC473327
0.5843	Remote Similarity	NPC39360
0.5843	Remote Similarity	NPC29763
0.5843	Remote Similarity	NPC210003
0.5843	Remote Similarity	NPC238376
0.5833	Remote Similarity	NPC39834
0.5806	Remote Similarity	NPC311830
0.58	Remote Similarity	NPC488089
0.5789	Remote Similarity	NPC8856
0.5778	Remote Similarity	NPC95090
0.5778	Remote Similarity	NPC27408
0.5773	Remote Similarity	NPC65563
0.5773	Remote Similarity	NPC470949
0.5773	Remote Similarity	NPC102028
0.5773	Remote Similarity	NPC150164
0.5745	Remote Similarity	NPC601586
0.5729	Remote Similarity	NPC29958
0.5714	Remote Similarity	NPC24043
0.5714	Remote Similarity	NPC27640
0.5699	Remote Similarity	NPC22832
0.5699	Remote Similarity	NPC21666
0.5699	Remote Similarity	NPC486578
0.5686	Remote Similarity	NPC470445
0.567	Remote Similarity	NPC471748
0.5667	Remote Similarity	NPC19709
0.5652	Remote Similarity	NPC117260
0.5591	Remote Similarity	NPC285197
0.5579	Remote Similarity	NPC190003
0.5556	Remote Similarity	NPC223860
0.5545	Remote Similarity	NPC122467
0.5543	Remote Similarity	NPC45638
0.5534	Remote Similarity	NPC292929
0.5534	Remote Similarity	NPC101636
0.5532	Remote Similarity	NPC243930
0.5532	Remote Similarity	NPC601144
0.5532	Remote Similarity	NPC609478
0.5524	Remote Similarity	NPC203145
0.5521	Remote Similarity	NPC254855
0.5521	Remote Similarity	NPC94610
0.5514	Remote Similarity	NPC164704
0.5495	Remote Similarity	NPC261866
0.5495	Remote Similarity	NPC470719
0.5495	Remote Similarity	NPC77672
0.5495	Remote Similarity	NPC133671
0.5495	Remote Similarity	NPC135391
0.5495	Remote Similarity	NPC78263
0.5495	Remote Similarity	NPC250069
0.5495	Remote Similarity	NPC470717
0.5484	Remote Similarity	NPC472459
0.5484	Remote Similarity	NPC59534
0.5484	Remote Similarity	NPC201292
0.5481	Remote Similarity	NPC602448
0.5474	Remote Similarity	NPC607707
0.5472	Remote Similarity	NPC470451
0.5464	Remote Similarity	NPC254540
0.5463	Remote Similarity	NPC311850
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC295625
0.5455	Remote Similarity	NPC303913
0.5446	Remote Similarity	NPC470720
0.5444	Remote Similarity	NPC67037
0.5444	Remote Similarity	NPC255615
0.5437	Remote Similarity	NPC471669
0.5437	Remote Similarity	NPC89127
0.5426	Remote Similarity	NPC307938
0.5426	Remote Similarity	NPC175107
0.5417	Remote Similarity	NPC203050
0.5417	Remote Similarity	NPC488072
0.5417	Remote Similarity	NPC225434
0.5413	Remote Similarity	NPC488083
0.5405	Remote Similarity	NPC198199
0.54	Remote Similarity	NPC115674
0.54	Remote Similarity	NPC255157
0.54	Remote Similarity	NPC259896
0.5392	Remote Similarity	NPC37668
0.5392	Remote Similarity	NPC72016
0.5392	Remote Similarity	NPC606657
0.5385	Remote Similarity	NPC470449
0.5376	Remote Similarity	NPC245014
0.5376	Remote Similarity	NPC305811
0.5376	Remote Similarity	NPC488080
0.5376	Remote Similarity	NPC169977
0.5376	Remote Similarity	NPC603655
0.537	Remote Similarity	NPC470715
0.5368	Remote Similarity	NPC120099
0.5361	Remote Similarity	NPC265115
0.5347	Remote Similarity	NPC46202
0.5347	Remote Similarity	NPC153755
0.5347	Remote Similarity	NPC64051
0.5333	Remote Similarity	NPC223426
0.5326	Remote Similarity	NPC127546
0.5326	Remote Similarity	NPC19388
0.5326	Remote Similarity	NPC240431
0.5326	Remote Similarity	NPC57625
0.5326	Remote Similarity	NPC55786
0.5326	Remote Similarity	NPC173637
0.5326	Remote Similarity	NPC317489
0.5326	Remote Similarity	NPC223424
0.5326	Remote Similarity	NPC600591
0.5315	Remote Similarity	NPC68592
0.53	Remote Similarity	NPC233994
0.53	Remote Similarity	NPC129827
0.5283	Remote Similarity	NPC244875
0.5283	Remote Similarity	NPC81042
0.5273	Remote Similarity	NPC470716

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC581172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5713
0.1-0.2	3362
0.2-0.3	64
0.3-0.4	4
0.4-0.5	3
0.5-0.6	0
0.6-0.7	3
0.7-0.8	1
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
0.7667	Intermediate Similarity	NPD7251	Phase 2
0.663	Remote Similarity	NPD6797	Phase 2
0.63	Remote Similarity	NPD7808	Phase 3
0.6186	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