NPASS Compound

Natural Product: NPC564370

Natural Product ID	NPC564370
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-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},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-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},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 10.3273 2.7267 0.7874 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7845 2.8818 2.0848 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4781 2.4719 2.2928 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7085 1.9183 1.2568 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4154 1.5151 1.4716 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5645 0.9249 0.4281 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0083 0.7154 -0.8590 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2315 0.1657 -1.8472 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6049 -0.0365 -3.0218 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9327 -0.1964 -1.5295 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0947 -0.7569 -2.4719 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5389 -0.9677 -3.7616 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7841 -1.1115 -2.1066 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0012 -1.6652 -3.0790 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0559 -3.0709 -3.3892 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3609 -0.8949 -0.8306 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1165 -1.2050 -0.4082 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0433 -1.7020 -0.9249 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1483 -0.8423 -0.7122 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1794 -1.3655 -1.4964 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2939 -0.4343 -1.7869 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9566 0.2033 -0.8364 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6706 -0.2813 0.1649 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0508 0.0994 0.0647 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0429 1.4911 -0.0451 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3151 1.9795 -0.6736 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7864 2.0996 1.3195 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7689 3.0300 1.2749 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3105 0.9455 2.2063 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9522 1.4759 3.4256 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1495 0.2938 1.4942 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1776 1.2561 1.2263 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6451 -2.7237 -1.0847 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3138 -3.6779 -2.0980 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7725 -3.0884 0.1322 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9269 -2.1737 1.1387 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3560 -3.1157 -0.3882 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3112 -4.0638 -1.4058 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2512 -0.3153 0.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5281 0.0301 -0.2312 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3322 0.5693 0.6862 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9016 1.6739 2.7405 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6451 2.2187 3.7788 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9508 2.6241 3.5558 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7079 3.1756 4.6006 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4253 1.6441 0.5070 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3262 3.1667 0.6732 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6524 3.1674 0.0297 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1518 1.8172 0.2958 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0198 0.9943 -1.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8512 -0.9322 -4.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7614 -3.1486 -4.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4069 -3.6710 -2.5453 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0477 -3.3868 -3.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0111 -1.8115 -2.0274 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6533 -1.4912 -2.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0739 -1.0921 -2.3374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9989 0.2508 -2.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7465 -1.3675 0.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2030 1.7941 -0.7084 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1277 2.0463 0.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1908 2.9910 -1.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6296 1.2613 -1.4741 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7083 2.5036 1.7875 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0196 3.8568 0.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1360 0.2160 2.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5551 1.1567 4.1399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7887 -0.5025 2.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7424 1.4910 2.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6978 -2.8754 -0.9241 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1298 -3.2018 -2.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0486 -4.1193 0.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3727 -2.6067 1.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6258 -3.3758 0.4168 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8842 -4.8945 -1.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8892 -0.1603 1.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8882 1.3692 2.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2595 2.3509 4.7805 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5106 3.7633 4.3713 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 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 13 16 2 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 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 20 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 16 39 1 0 39 40 2 0 40 41 1 0 5 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 44 3 1 0 41 6 1 0 40 10 1 0 37 18 1 0 31 23 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 7 50 1 0 12 51 1 0 15 52 1 0 15 53 1 0 15 54 1 0 18 55 1 6 20 56 1 6 21 57 1 0 21 58 1 0 23 59 1 1 25 60 1 6 26 61 1 0 26 62 1 0 26 63 1 0 27 64 1 1 28 65 1 0 29 66 1 1 30 67 1 0 31 68 1 1 32 69 1 0 33 70 1 1 34 71 1 0 35 72 1 1 36 73 1 0 37 74 1 1 38 75 1 0 39 76 1 0 42 77 1 0 43 78 1 0 45 79 1 0 M END

Standard InCHIKey	PYPKJBUJNZMSTH-KXZPRJKRSA-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)7-14(43-16)11-4-5-12(30)15(6-11)39-2/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(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)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.18	Volume:	586.91 ? Van der Waals volume.
Dense:	1.087	LogP:	0.708 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.117 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.393 ? 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:	4.772	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:	0.589	Fluc inhibitor:	0.259 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.922 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.756 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.044	Promiscuous compounds:	0.387

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.229	MDCK Permeability:	-5.414
Pgp-inhibitor:	0.0	Pgp-substrate:	0.899
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):	0.925
20% Bioavailability (F20%):	0.629	30% Bioavailability (F30%):	0.978
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.736
Plasma Protein Binding (PPB):	84.669%	Volume Distribution (VD):	-0.095
Fu:	13.339% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.783
BSEP inhibitor:	0.003

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:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.031 ? 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):

1.525

Half-life (T1/2):

3.779

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.091
Human Hepatotoxicity (H-HT):	0.454	Drug-induced Liver Injury (DILI):	0.949
AMES Toxicity:	0.963	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.048	Skin Sensitization:	0.998
Carcinogencity:	0.154	Eye Corrosion:	0.0
Eye Irritation:	0.216	Respiratory Toxicity:	0.046
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.897
Hematotoxicity:	0.428	Drug-induced Nephrotoxicity:	0.619
Genotoxicity:	0.869	RPMI-8226 Immunitoxicity:	0.366
A549 Cytotoxicity:	0.879	Hek293 Cytotoxicity:	0.744
BCF:	0.344 ? 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:	2.939 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.399 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.624 ? 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
NPO5586	Kickxia elatine	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5586	Kickxia elatine	Species	Plantaginaceae	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 NPC564370 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	18537
0.1-0.2	27280
0.2-0.3	3053
0.3-0.4	638
0.4-0.5	241
0.5-0.6	80
0.6-0.7	19
0.7-0.8	0
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
0.8161	Intermediate Similarity	NPC204693
0.7356	Intermediate Similarity	NPC602805
0.6813	Remote Similarity	NPC211594
0.6778	Remote Similarity	NPC99957
0.6774	Remote Similarity	NPC44931
0.6771	Remote Similarity	NPC483707
0.6771	Remote Similarity	NPC209296
0.6702	Remote Similarity	NPC22062
0.6702	Remote Similarity	NPC473634
0.6702	Remote Similarity	NPC210073
0.6702	Remote Similarity	NPC138811
0.663	Remote Similarity	NPC172807
0.6559	Remote Similarity	NPC254540
0.6465	Remote Similarity	NPC476472
0.6465	Remote Similarity	NPC294815
0.6465	Remote Similarity	NPC16194
0.6224	Remote Similarity	NPC475366
0.6154	Remote Similarity	NPC105025
0.6129	Remote Similarity	NPC606560
0.6087	Remote Similarity	NPC201292
0.6	Remote Similarity	NPC470443
0.598	Remote Similarity	NPC473073
0.5976	Remote Similarity	NPC47781
0.596	Remote Similarity	NPC473571
0.596	Remote Similarity	NPC110941
0.59	Remote Similarity	NPC126784
0.59	Remote Similarity	NPC241423
0.5895	Remote Similarity	NPC311830
0.5851	Remote Similarity	NPC609451
0.5833	Remote Similarity	NPC488072
0.5825	Remote Similarity	NPC195257
0.5806	Remote Similarity	NPC186807
0.5758	Remote Similarity	NPC67105
0.5745	Remote Similarity	NPC475942
0.57	Remote Similarity	NPC233994
0.5699	Remote Similarity	NPC93337
0.5644	Remote Similarity	NPC186816
0.5638	Remote Similarity	NPC45638
0.5631	Remote Similarity	NPC473623
0.5625	Remote Similarity	NPC605067
0.5619	Remote Similarity	NPC101636
0.5591	Remote Similarity	NPC58053
0.5577	Remote Similarity	NPC488089
0.5545	Remote Similarity	NPC473512
0.5545	Remote Similarity	NPC129827
0.5534	Remote Similarity	NPC211532
0.5534	Remote Similarity	NPC488364
0.5526	Remote Similarity	NPC488079
0.5481	Remote Similarity	NPC473327
0.5464	Remote Similarity	NPC601144
0.5463	Remote Similarity	NPC89052
0.5463	Remote Similarity	NPC11468
0.5446	Remote Similarity	NPC173582
0.5446	Remote Similarity	NPC265885
0.5446	Remote Similarity	NPC181465
0.5446	Remote Similarity	NPC215710
0.5446	Remote Similarity	NPC473438
0.5446	Remote Similarity	NPC253788
0.5392	Remote Similarity	NPC203259
0.5392	Remote Similarity	NPC65563
0.5392	Remote Similarity	NPC33054
0.5392	Remote Similarity	NPC470949
0.5392	Remote Similarity	NPC176740
0.5392	Remote Similarity	NPC471725
0.5392	Remote Similarity	NPC134532
0.5392	Remote Similarity	NPC602582
0.5385	Remote Similarity	NPC65711
0.5364	Remote Similarity	NPC173837
0.5347	Remote Similarity	NPC187379
0.5319	Remote Similarity	NPC331652
0.5312	Remote Similarity	NPC27640
0.5306	Remote Similarity	NPC181616
0.53	Remote Similarity	NPC4390
0.5294	Remote Similarity	NPC15358
0.5294	Remote Similarity	NPC227508
0.5288	Remote Similarity	NPC284277
0.5288	Remote Similarity	NPC475497
0.5288	Remote Similarity	NPC153755
0.5263	Remote Similarity	NPC19709
0.5225	Remote Similarity	NPC472993
0.5217	Remote Similarity	NPC198199
0.5185	Remote Similarity	NPC298171
0.5179	Remote Similarity	NPC473644
0.5158	Remote Similarity	NPC114740
0.5152	Remote Similarity	NPC601710
0.5143	Remote Similarity	NPC46202
0.5143	Remote Similarity	NPC488073
0.5143	Remote Similarity	NPC64051
0.5135	Remote Similarity	NPC473072
0.5133	Remote Similarity	NPC311850
0.5102	Remote Similarity	NPC117260
0.51	Remote Similarity	NPC223747
0.51	Remote Similarity	NPC607707
0.5094	Remote Similarity	NPC483415
0.5093	Remote Similarity	NPC231194
0.5085	Remote Similarity	NPC120952
0.5056	Remote Similarity	NPC469622
0.5049	Remote Similarity	NPC295613
0.5049	Remote Similarity	NPC473657
0.5047	Remote Similarity	NPC483416
0.5047	Remote Similarity	NPC229409

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC564370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5297
0.1-0.2	3794
0.2-0.3	48
0.3-0.4	6
0.4-0.5	0
0.5-0.6	4
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
0.6771	Remote Similarity	NPD7054	Phase 4
0.5905	Remote Similarity	NPD7472	Pre-clinical
0.5392	Remote Similarity	NPD6797	Phase 2
0.5377	Remote Similarity	NPD7251	Phase 2
0.5182	Remote Similarity	NPD7808	Phase 3

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