NPASS Compound

Natural Product: NPC575138

Natural Product ID	NPC575138
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-methoxyphenyl)-3,7-bis[[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy]chromen-4-one
IUPAC Name	5-hydroxy-2-(4-methoxyphenyl)-3,7-bis[[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-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 74 78 0 0 0 0 0 0 0 0999 V2000 -5.0882 5.1142 3.5203 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7285 4.7590 3.8030 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1302 3.8584 2.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7679 3.2996 1.8600 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1724 2.3969 0.9960 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8782 2.0255 1.2132 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1600 1.0604 0.4274 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7262 0.1773 -0.4319 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0871 0.0440 -0.6830 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8583 -0.9462 0.0134 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9727 -2.0885 -0.7974 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9281 -1.9969 -1.7651 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9271 -3.1651 -1.7100 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5948 -0.6850 -1.9623 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8826 0.1308 -2.8673 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9455 0.0698 -0.7077 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3031 0.0052 -0.4027 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1617 -0.4535 0.4775 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9211 -1.4397 1.1313 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9051 -0.7095 -1.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3987 -1.5462 -1.9581 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4541 -0.6839 -0.9671 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3143 -1.5252 -1.6312 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7784 -2.4388 -2.5200 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6974 -1.4574 -1.4119 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2183 -0.5473 -0.5283 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5532 -0.4324 -0.2724 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5666 -1.1848 -0.8310 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2938 -1.8650 0.1642 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8566 -0.8849 1.0081 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2821 -1.5782 2.2871 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0679 -0.3097 0.2805 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0784 1.0664 0.4448 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9204 -0.6008 -1.2105 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1136 -1.9806 -1.4040 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5086 -0.2753 -1.6029 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3433 -0.4710 -2.9642 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3129 0.2922 0.1288 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9572 0.2320 -0.0803 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1685 1.0278 0.5501 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2354 2.5903 2.3053 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8100 3.4815 3.1650 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1997 5.4399 2.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7236 4.2110 3.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4148 5.8661 4.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7980 3.5817 1.6701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7467 2.0085 0.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2391 -1.2800 0.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3774 -2.1884 -2.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1641 -3.4715 -0.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4717 -4.0766 -2.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8088 -2.9195 -2.3402 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5768 -0.8955 -2.4823 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9156 -0.2377 -3.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7162 1.1383 -0.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6511 -0.8878 -0.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0584 0.3524 1.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6869 -1.4619 2.0704 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2596 -3.2718 -2.8323 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2787 -2.1474 -1.9703 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1992 -1.9682 -1.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0913 -0.1317 1.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5477 -1.3451 3.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3350 -2.6769 2.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2693 -1.1804 2.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0170 -0.7590 0.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3307 1.5291 -0.4045 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6553 0.0025 -1.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3886 -2.3677 -1.9386 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2683 0.7799 -1.3780 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7528 -1.2559 -3.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7259 1.0119 0.8281 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1874 2.3263 2.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2858 3.9095 4.0150 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 12 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 8 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 26 38 1 0 38 39 2 0 39 40 1 0 6 41 1 0 41 42 2 0 42 3 1 0 40 7 1 0 18 10 1 0 39 22 1 0 36 28 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 5 47 1 0 10 48 1 1 12 49 1 6 13 50 1 0 13 51 1 0 13 52 1 0 14 53 1 6 15 54 1 0 16 55 1 6 17 56 1 0 18 57 1 1 19 58 1 0 24 59 1 0 25 60 1 0 28 61 1 6 30 62 1 1 31 63 1 0 31 64 1 0 31 65 1 0 32 66 1 1 33 67 1 0 34 68 1 6 35 69 1 0 36 70 1 6 37 71 1 0 38 72 1 0 41 73 1 0 42 74 1 0 M END

Standard InCHIKey	YJFHLDPUBWHTMO-OTRCQNDTSA-N
Standard InCHI	InChI=1S/C28H32O14/c1-10-18(30)21(33)23(35)27(38-10)40-14-8-15(29)17-16(9-14)41-25(12-4-6-13(37-3)7-5-12)26(20(17)32)42-28-24(36)22(34)19(31)11(2)39-28/h4-11,18-19,21-24,27-31,33-36H,1-3H3/t10-,11-,18-,19-,21+,22+,23+,24+,27-,28-/m0/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C(=O)C3=C(O)C=C(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	592.18	Volume:	552.033 ? Van der Waals volume.
Dense:	1.073	LogP:	1.518 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.855 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.723 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	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:	0.194	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.593	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0.632	Fluc inhibitor:	0.321 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.871 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.649 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.115	Promiscuous compounds:	0.382

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.23	MDCK Permeability:	-5.245
Pgp-inhibitor:	0.005	Pgp-substrate:	0.974
PAMPA:	1.0 ? 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):	0.4
20% Bioavailability (F20%):	0.035	30% Bioavailability (F30%):	0.308
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.064
Plasma Protein Binding (PPB):	87.272%	Volume Distribution (VD):	-0.047
Fu:	12.189% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.966
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.461
BSEP inhibitor:	0.343

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.673 ? 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):

1.783

Half-life (T1/2):

4.26

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.26
Human Hepatotoxicity (H-HT):	0.518	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.88	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	0.926
Carcinogencity:	0.043	Eye Corrosion:	0.0
Eye Irritation:	0.035	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.959
Hematotoxicity:	0.11	Drug-induced Nephrotoxicity:	0.679
Genotoxicity:	0.339	RPMI-8226 Immunitoxicity:	0.202
A549 Cytotoxicity:	0.117	Hek293 Cytotoxicity:	0.171
BCF:	0.563 ? 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:	3.347 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.846 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.104 ? 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
NPO47091	Asplenium bulbiferum	Species	Aspleniaceae	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 NPC575138 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	17178
0.1-0.2	28635
0.2-0.3	2969
0.3-0.4	545
0.4-0.5	299
0.5-0.6	126
0.6-0.7	58
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8732	High Similarity	NPC611303
0.8451	Intermediate Similarity	NPC46420
0.8429	Intermediate Similarity	NPC249281
0.8194	Intermediate Similarity	NPC271692
0.8056	Intermediate Similarity	NPC158674
0.7917	Intermediate Similarity	NPC289667
0.7763	Intermediate Similarity	NPC116458
0.7763	Intermediate Similarity	NPC246943
0.7692	Intermediate Similarity	NPC251417
0.7662	Intermediate Similarity	NPC276377
0.7532	Intermediate Similarity	NPC605784
0.747	Intermediate Similarity	NPC606657
0.7195	Intermediate Similarity	NPC150164
0.7108	Intermediate Similarity	NPC186816
0.7105	Intermediate Similarity	NPC297987
0.7059	Intermediate Similarity	NPC72016
0.6883	Remote Similarity	NPC136042
0.686	Remote Similarity	NPC32641
0.686	Remote Similarity	NPC256188
0.686	Remote Similarity	NPC35119
0.6835	Remote Similarity	NPC219904
0.6795	Remote Similarity	NPC84362
0.6795	Remote Similarity	NPC27640
0.6709	Remote Similarity	NPC472459
0.6627	Remote Similarity	NPC278419
0.6627	Remote Similarity	NPC179198
0.6623	Remote Similarity	NPC111929
0.6623	Remote Similarity	NPC320283
0.6623	Remote Similarity	NPC41121
0.6538	Remote Similarity	NPC19709
0.6538	Remote Similarity	NPC238376
0.65	Remote Similarity	NPC59534
0.6456	Remote Similarity	NPC95090
0.6456	Remote Similarity	NPC265530
0.6456	Remote Similarity	NPC27408
0.6437	Remote Similarity	NPC240306
0.6437	Remote Similarity	NPC64425
0.6418	Remote Similarity	NPC262094
0.641	Remote Similarity	NPC473043
0.641	Remote Similarity	NPC331652
0.6404	Remote Similarity	NPC5319
0.6395	Remote Similarity	NPC22062
0.6395	Remote Similarity	NPC473634
0.6395	Remote Similarity	NPC138811
0.6375	Remote Similarity	NPC305811
0.6375	Remote Similarity	NPC181712
0.6375	Remote Similarity	NPC349108
0.6329	Remote Similarity	NPC127546
0.6329	Remote Similarity	NPC57625
0.6329	Remote Similarity	NPC108831
0.6329	Remote Similarity	NPC173637
0.6329	Remote Similarity	NPC317489
0.6329	Remote Similarity	NPC223424
0.6329	Remote Similarity	NPC182634
0.6329	Remote Similarity	NPC600591
0.631	Remote Similarity	NPC265115
0.6265	Remote Similarity	NPC223747
0.625	Remote Similarity	NPC64305
0.6222	Remote Similarity	NPC142142
0.6203	Remote Similarity	NPC135599
0.6203	Remote Similarity	NPC73855
0.6203	Remote Similarity	NPC113968
0.6203	Remote Similarity	NPC328940
0.6203	Remote Similarity	NPC277174
0.6203	Remote Similarity	NPC160515
0.6203	Remote Similarity	NPC606877
0.619	Remote Similarity	NPC355481
0.618	Remote Similarity	NPC483414
0.6146	Remote Similarity	NPC277532
0.6129	Remote Similarity	NPC14187
0.6064	Remote Similarity	NPC121703
0.6044	Remote Similarity	NPC486577
0.6042	Remote Similarity	NPC25523
0.6	Remote Similarity	NPC483415
0.5977	Remote Similarity	NPC480466
0.5952	Remote Similarity	NPC22832
0.5934	Remote Similarity	NPC483416
0.5934	Remote Similarity	NPC209296
0.5876	Remote Similarity	NPC480441
0.5862	Remote Similarity	NPC480463
0.5806	Remote Similarity	NPC475382
0.58	Remote Similarity	NPC295625
0.5783	Remote Similarity	NPC24043
0.5765	Remote Similarity	NPC243930
0.5765	Remote Similarity	NPC120099
0.5765	Remote Similarity	NPC486578
0.5761	Remote Similarity	NPC473327
0.5758	Remote Similarity	NPC470716
0.5732	Remote Similarity	NPC348541
0.573	Remote Similarity	NPC267680
0.5714	Remote Similarity	NPC46202
0.5714	Remote Similarity	NPC470715
0.5694	Remote Similarity	NPC153758
0.5682	Remote Similarity	NPC487212
0.5667	Remote Similarity	NPC293626
0.5652	Remote Similarity	NPC470443
0.5647	Remote Similarity	NPC285197
0.5647	Remote Similarity	NPC488071
0.5631	Remote Similarity	NPC470720
0.5591	Remote Similarity	NPC473623
0.5581	Remote Similarity	NPC21666
0.5577	Remote Similarity	NPC209550
0.5556	Remote Similarity	NPC173582
0.5556	Remote Similarity	NPC265885
0.5556	Remote Similarity	NPC181465
0.5556	Remote Similarity	NPC215710
0.5556	Remote Similarity	NPC67105
0.5556	Remote Similarity	NPC473438
0.5556	Remote Similarity	NPC164704
0.5556	Remote Similarity	NPC253788
0.5542	Remote Similarity	NPC77672
0.5542	Remote Similarity	NPC133671
0.5542	Remote Similarity	NPC135391
0.5542	Remote Similarity	NPC78263
0.5542	Remote Similarity	NPC250069
0.5534	Remote Similarity	NPC470717
0.5532	Remote Similarity	NPC488089
0.5529	Remote Similarity	NPC27942
0.5524	Remote Similarity	NPC175429
0.5517	Remote Similarity	NPC607707
0.5495	Remote Similarity	NPC210073
0.5493	Remote Similarity	NPC103904
0.5479	Remote Similarity	NPC270620
0.5476	Remote Similarity	NPC277205
0.5476	Remote Similarity	NPC37919
0.5476	Remote Similarity	NPC189142
0.5476	Remote Similarity	NPC77660
0.5465	Remote Similarity	NPC60735
0.5465	Remote Similarity	NPC175107
0.5465	Remote Similarity	NPC26230
0.5455	Remote Similarity	NPC66087
0.5455	Remote Similarity	NPC190003
0.5435	Remote Similarity	NPC473571
0.5435	Remote Similarity	NPC110941
0.5429	Remote Similarity	NPC138990
0.5426	Remote Similarity	NPC482026
0.5417	Remote Similarity	NPC146679
0.5412	Remote Similarity	NPC488080
0.5412	Remote Similarity	NPC169977
0.5405	Remote Similarity	NPC236769
0.5402	Remote Similarity	NPC148710
0.5402	Remote Similarity	NPC609478
0.5385	Remote Similarity	NPC44931
0.5385	Remote Similarity	NPC470719
0.5385	Remote Similarity	NPC227508
0.5376	Remote Similarity	NPC126784
0.5376	Remote Similarity	NPC241423
0.5361	Remote Similarity	NPC135358
0.5357	Remote Similarity	NPC261866
0.5357	Remote Similarity	NPC39360
0.5357	Remote Similarity	NPC29763
0.5357	Remote Similarity	NPC210003
0.5349	Remote Similarity	NPC42773
0.5349	Remote Similarity	NPC45522
0.5349	Remote Similarity	NPC325555
0.5349	Remote Similarity	NPC226304
0.5349	Remote Similarity	NPC599850
0.5341	Remote Similarity	NPC311830
0.5326	Remote Similarity	NPC203259
0.5326	Remote Similarity	NPC33054
0.5326	Remote Similarity	NPC176740
0.5326	Remote Similarity	NPC471725
0.5326	Remote Similarity	NPC134532
0.5326	Remote Similarity	NPC602582
0.5312	Remote Similarity	NPC476472
0.5312	Remote Similarity	NPC294815
0.5312	Remote Similarity	NPC470447
0.5312	Remote Similarity	NPC16194
0.5294	Remote Similarity	NPC145038
0.5294	Remote Similarity	NPC56077
0.5294	Remote Similarity	NPC281131
0.5294	Remote Similarity	NPC253662
0.5294	Remote Similarity	NPC179950
0.5294	Remote Similarity	NPC323593
0.5294	Remote Similarity	NPC88789
0.5294	Remote Similarity	NPC203500
0.5294	Remote Similarity	NPC491374
0.5281	Remote Similarity	NPC203050
0.5281	Remote Similarity	NPC488072
0.5281	Remote Similarity	NPC225434
0.5281	Remote Similarity	NPC476215
0.5275	Remote Similarity	NPC609888
0.5269	Remote Similarity	NPC204693
0.5258	Remote Similarity	NPC470445
0.5253	Remote Similarity	NPC11468
0.5233	Remote Similarity	NPC186807
0.5233	Remote Similarity	NPC73511
0.5227	Remote Similarity	NPC80188
0.5227	Remote Similarity	NPC608742
0.5222	Remote Similarity	NPC116864
0.5222	Remote Similarity	NPC244776
0.5217	Remote Similarity	NPC39834
0.5213	Remote Similarity	NPC153755
0.5205	Remote Similarity	NPC110070
0.5205	Remote Similarity	NPC188871
0.5181	Remote Similarity	NPC288084
0.5176	Remote Similarity	NPC19388
0.5176	Remote Similarity	NPC58053
0.5176	Remote Similarity	NPC240431
0.5176	Remote Similarity	NPC55786

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC575138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4462
0.1-0.2	4585
0.2-0.3	91
0.3-0.4	6
0.4-0.5	1
0.5-0.6	2
0.6-0.7	3
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
0.6404	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7808	Phase 3
0.6154	Remote Similarity	NPD7251	Phase 2
0.5934	Remote Similarity	NPD7054	Phase 4
0.5326	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