NPASS Compound

Natural Product: NPC557159

Natural Product ID	NPC557159
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-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 79 83 0 0 0 0 0 0 0 0999 V2000 10.8452 0.1152 -3.9026 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7780 -0.4316 -2.6139 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6422 -0.5146 -1.8316 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4024 -0.0482 -2.2586 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2840 -0.1393 -1.4663 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3656 -0.7122 -0.1902 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1504 -0.7935 0.6375 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2380 -1.3445 1.8877 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1175 -1.4388 2.6973 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1202 -1.9278 3.8454 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9236 -0.9442 2.1601 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7607 -0.9828 2.8653 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8155 -1.5402 4.1486 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5594 -0.5018 2.3678 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4496 -0.6091 3.2132 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2080 0.3684 4.2224 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5015 0.0420 1.1133 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4051 0.5465 0.4932 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9316 0.6702 0.8058 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6437 -0.0053 -0.1818 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0251 -0.0680 0.0247 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6318 -0.1392 -1.3261 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9268 -0.1966 -1.5479 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8488 0.7250 -1.3241 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7859 0.2316 -0.4089 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3583 -0.9490 -0.7520 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6461 -1.0807 0.0693 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5981 -1.2132 -2.1827 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0835 -2.4805 -2.5534 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1759 -0.1711 -3.1513 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1940 0.1572 -4.0757 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7019 1.0981 -2.5334 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8133 1.7748 -2.0260 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5312 0.8678 1.0280 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2811 0.3085 2.3245 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8317 2.2057 1.0463 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3766 3.1034 0.1032 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3434 2.1300 0.9360 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7058 2.6149 2.0846 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7177 0.0770 0.3902 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8928 -0.4004 0.8968 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0081 -0.3446 0.1807 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5955 -1.1614 0.2028 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7236 -1.0735 -0.5873 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9666 -1.5471 -0.1447 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8668 0.4782 -4.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5228 -0.6651 -4.6397 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1903 1.0055 -3.9359 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3748 0.3922 -3.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3387 0.2295 -1.8215 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1536 -1.7321 2.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9029 -0.9280 4.9269 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4949 -0.0149 5.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8672 0.6263 4.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7717 1.2753 3.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1116 0.2122 1.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1633 -1.1160 0.4663 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1871 -1.1053 -1.7770 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0730 0.6287 -1.9487 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4708 1.6781 -0.9265 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6981 -1.7687 -0.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2508 -1.9414 -0.2778 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3638 -1.2499 1.1314 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2684 -0.1800 -0.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7143 -1.3421 -2.3256 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5234 -3.2087 -2.0833 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3645 -0.6089 -3.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7329 0.6097 -4.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1984 1.7698 -3.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 2.6964 -1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6156 0.9510 1.0114 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6113 -0.6080 2.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0644 2.6996 2.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8967 2.9139 -0.7396 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9337 2.7405 0.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8682 3.5645 2.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7040 0.5061 -0.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7373 -1.6135 1.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3831 -1.1723 0.6995 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 14 17 2 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 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 21 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 17 40 1 0 40 41 2 0 41 42 1 0 6 43 1 0 43 44 2 0 44 45 1 0 44 3 1 0 42 7 1 0 41 11 1 0 38 19 1 0 32 24 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 5 50 1 0 8 51 1 0 13 52 1 0 16 53 1 0 16 54 1 0 16 55 1 0 19 56 1 1 21 57 1 1 22 58 1 0 22 59 1 0 24 60 1 1 26 61 1 1 27 62 1 0 27 63 1 0 27 64 1 0 28 65 1 1 29 66 1 0 30 67 1 6 31 68 1 0 32 69 1 6 33 70 1 0 34 71 1 6 35 72 1 0 36 73 1 1 37 74 1 0 38 75 1 6 39 76 1 0 40 77 1 0 43 78 1 0 45 79 1 0 M END

Standard InCHIKey	DEDMNYYOJUBPSV-BREQBEEASA-N
Standard InCHI	InChI=1S/C29H34O16/c1-10-20(32)23(35)25(37)28(42-10)41-9-18-21(33)24(36)26(38)29(45-18)44-17-8-16-19(22(34)27(17)40-3)13(31)7-15(43-16)11-4-5-14(39-2)12(30)6-11/h4-8,10,18,20-21,23-26,28-30,32-38H,9H2,1-3H3/t10-,18+,20-,21+,23+,24-,25+,26+,28+,29+/m0/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=C(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.18	Volume:	586.91 ? Van der Waals volume.
Dense:	1.087	LogP:	0.507 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.058 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.517 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	247.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.781	Fsp³:	0.483
MCE-18:	121.279 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.582	Fluc inhibitor:	0.268 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.883 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.667 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.047	Promiscuous compounds:	0.389

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.191	MDCK Permeability:	-5.388
Pgp-inhibitor:	0.003	Pgp-substrate:	0.911
PAMPA:	0.993 ? 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):	0.774
20% Bioavailability (F20%):	0.148	30% Bioavailability (F30%):	0.931
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.513
Plasma Protein Binding (PPB):	82.243%	Volume Distribution (VD):	-0.144
Fu:	14.63% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.489
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.012
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.944
HLM stability:	0.017 ? 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):

1.408

Half-life (T1/2):

4.672

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.157
Human Hepatotoxicity (H-HT):	0.34	Drug-induced Liver Injury (DILI):	0.81
AMES Toxicity:	0.829	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.026	Skin Sensitization:	0.948
Carcinogencity:	0.047	Eye Corrosion:	0.0
Eye Irritation:	0.117	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.944
Hematotoxicity:	0.102	Drug-induced Nephrotoxicity:	0.399
Genotoxicity:	0.311	RPMI-8226 Immunitoxicity:	0.244
A549 Cytotoxicity:	0.259	Hek293 Cytotoxicity:	0.34
BCF:	0.273 ? 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:	2.86 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.387 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.575 ? 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
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19299148]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22210168]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[22210168]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[2691636]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2691636]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2865	Abrus precatorius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2865	Abrus precatorius	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 NPC557159 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	15826
0.1-0.2	29590
0.2-0.3	3422
0.3-0.4	667
0.4-0.5	248
0.5-0.6	79
0.6-0.7	14
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.869	High Similarity	NPC204693
0.8182	Intermediate Similarity	NPC209296
0.7273	Intermediate Similarity	NPC211594
0.7204	Intermediate Similarity	NPC483707
0.7143	Intermediate Similarity	NPC22062
0.7143	Intermediate Similarity	NPC473634
0.7143	Intermediate Similarity	NPC138811
0.6813	Remote Similarity	NPC254540
0.6774	Remote Similarity	NPC210073
0.6742	Remote Similarity	NPC605067
0.6667	Remote Similarity	NPC99957
0.6522	Remote Similarity	NPC172807
0.6495	Remote Similarity	NPC473327
0.6489	Remote Similarity	NPC44931
0.6289	Remote Similarity	NPC475366
0.6262	Remote Similarity	NPC198199
0.6222	Remote Similarity	NPC186807
0.6154	Remote Similarity	NPC201292
0.6091	Remote Similarity	NPC120952
0.6	Remote Similarity	NPC58053
0.6	Remote Similarity	NPC473623
0.5957	Remote Similarity	NPC602805
0.5941	Remote Similarity	NPC488089
0.5926	Remote Similarity	NPC160951
0.5914	Remote Similarity	NPC609451
0.59	Remote Similarity	NPC470443
0.5882	Remote Similarity	NPC473073
0.587	Remote Similarity	NPC105025
0.5851	Remote Similarity	NPC22832
0.5851	Remote Similarity	NPC21666
0.581	Remote Similarity	NPC11468
0.58	Remote Similarity	NPC126784
0.58	Remote Similarity	NPC241423
0.5758	Remote Similarity	NPC233994
0.5714	Remote Similarity	NPC187379
0.57	Remote Similarity	NPC473571
0.57	Remote Similarity	NPC110941
0.5699	Remote Similarity	NPC45638
0.5657	Remote Similarity	NPC67105
0.5588	Remote Similarity	NPC211532
0.5588	Remote Similarity	NPC488364
0.5577	Remote Similarity	NPC476472
0.5577	Remote Similarity	NPC294815
0.5577	Remote Similarity	NPC16194
0.5545	Remote Similarity	NPC186816
0.5524	Remote Similarity	NPC101636
0.5505	Remote Similarity	NPC473644
0.55	Remote Similarity	NPC227508
0.5455	Remote Similarity	NPC311850
0.5437	Remote Similarity	NPC65711
0.5426	Remote Similarity	NPC93337
0.5417	Remote Similarity	NPC611303
0.54	Remote Similarity	NPC295613
0.54	Remote Similarity	NPC473657
0.5347	Remote Similarity	NPC173582
0.5347	Remote Similarity	NPC265885
0.5347	Remote Similarity	NPC181465
0.5347	Remote Similarity	NPC215710
0.5347	Remote Similarity	NPC473438
0.5347	Remote Similarity	NPC253788
0.534	Remote Similarity	NPC46202
0.534	Remote Similarity	NPC284277
0.534	Remote Similarity	NPC475497
0.5319	Remote Similarity	NPC19709
0.531	Remote Similarity	NPC68592
0.5294	Remote Similarity	NPC473512
0.5294	Remote Similarity	NPC203259
0.5294	Remote Similarity	NPC129827
0.5294	Remote Similarity	NPC475155
0.5294	Remote Similarity	NPC33054
0.5294	Remote Similarity	NPC176740
0.5294	Remote Similarity	NPC471725
0.5294	Remote Similarity	NPC134532
0.5294	Remote Similarity	NPC602582
0.5238	Remote Similarity	NPC51326
0.5213	Remote Similarity	NPC473043
0.5213	Remote Similarity	NPC114740
0.5208	Remote Similarity	NPC27640
0.5204	Remote Similarity	NPC181616
0.5196	Remote Similarity	NPC15358
0.5196	Remote Similarity	NPC39834
0.5185	Remote Similarity	NPC135358
0.5169	Remote Similarity	NPC262222
0.5152	Remote Similarity	NPC607707
0.5146	Remote Similarity	NPC65563
0.5146	Remote Similarity	NPC470949
0.5143	Remote Similarity	NPC483414
0.5143	Remote Similarity	NPC483415
0.514	Remote Similarity	NPC475382
0.5114	Remote Similarity	NPC469622
0.5102	Remote Similarity	NPC191306
0.5102	Remote Similarity	NPC219904
0.5094	Remote Similarity	NPC483416
0.5094	Remote Similarity	NPC229409
0.5093	Remote Similarity	NPC298171
0.5053	Remote Similarity	NPC331652
0.5052	Remote Similarity	NPC181712
0.5048	Remote Similarity	NPC488073
0.5047	Remote Similarity	NPC142142
0.5043	Remote Similarity	NPC488086

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC557159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4749
0.1-0.2	4326
0.2-0.3	64
0.3-0.4	5
0.4-0.5	1
0.5-0.6	3
0.6-0.7	0
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	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD7054	Phase 4
0.7113	Intermediate Similarity	NPD7472	Pre-clinical
0.5514	Remote Similarity	NPD7808	Phase 3
0.5294	Remote Similarity	NPD6797	Phase 2
0.5283	Remote Similarity	NPD7251	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