NPASS Compound

Natural Product: NPC584331

Natural Product ID	NPC584331
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)-6,7-dimethoxy-3-[(2~{S},3~{R},4~{S},5~{R},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-(4-hydroxy-3-methoxy-phenyl)-6,7-dimethoxy-3-[(2~{S},3~{R},4~{S},5~{R},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 83 87 0 0 0 0 0 0 0 0999 V2000 -0.7241 3.4657 -3.7932 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7862 2.7071 -4.3079 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6799 2.0035 -3.6146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7435 1.8007 -2.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6835 1.0690 -1.5980 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7095 0.7260 -0.1877 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6349 0.8668 0.6310 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4214 1.3226 0.2377 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2889 0.4924 -0.0081 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8282 1.2375 0.2596 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9469 0.4545 0.4717 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2014 1.1213 -0.1042 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2921 0.3045 0.1130 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4631 0.8046 -0.4220 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9689 -0.0704 -1.3931 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5254 -1.1983 -0.8221 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8349 -2.1953 -1.9111 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8284 -0.8710 -0.1150 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9599 -1.6919 1.0149 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8584 0.5974 0.2752 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2628 1.3791 -0.8060 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4678 1.0350 0.6848 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5134 2.3996 0.9425 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7917 -0.9375 -0.1100 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0534 -1.4916 -0.3194 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1083 -0.8962 -1.4476 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9676 -0.3984 -2.3913 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2104 -0.1120 -1.3664 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2735 -0.9883 -1.6300 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 0.4896 1.9751 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8509 0.6068 2.7537 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9986 -0.0056 2.4406 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1894 -0.4161 3.7681 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1473 -0.3012 4.6535 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4228 -0.9372 4.1910 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5504 -1.3252 5.4969 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2297 -2.6755 5.8762 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4179 -1.0299 3.2933 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7072 -1.5331 3.5782 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7226 -1.5160 2.6403 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2411 -0.6272 1.9859 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0262 -0.1136 1.5409 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8638 0.2410 0.3052 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6714 0.4798 -2.4200 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6766 0.6349 -3.7852 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7037 1.3783 -4.3707 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7132 1.5306 -5.7629 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3886 3.0293 -2.8155 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0413 4.5322 -3.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1758 3.5109 -4.4296 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9394 2.3099 -1.6820 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3205 -0.3764 0.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0792 0.3375 1.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0509 1.2539 -1.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3257 2.1301 0.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2313 1.7595 -0.9288 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8075 -1.7116 -0.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9083 -2.7817 -2.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2423 -1.6401 -2.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6173 -2.8862 -1.5236 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6789 -1.0857 -0.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8768 -1.1154 1.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5189 0.7242 1.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2998 0.7827 -1.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1585 0.5161 1.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6102 2.6892 1.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2626 -1.6401 0.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3905 -2.0120 0.4420 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8760 -1.9522 -1.7272 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3790 -1.0856 -2.9864 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1471 0.6299 -2.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1565 -1.8475 -1.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2693 -0.7751 4.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9900 -2.7322 6.9367 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3741 -3.0513 5.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1054 -3.2849 5.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4230 -2.0390 1.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6966 -1.8558 2.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8703 -0.4471 2.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0188 -0.6799 1.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4458 -0.1111 -1.9560 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4638 0.1603 -4.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6209 1.6197 -6.2017 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 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 16 17 1 0 16 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 11 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 7 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 0 35 38 2 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 2 0 42 43 1 0 5 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 46 3 1 0 43 6 1 0 28 9 1 0 42 32 1 0 22 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 4 51 1 0 9 52 1 1 11 53 1 1 12 54 1 0 12 55 1 0 14 56 1 6 16 57 1 1 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 6 19 62 1 0 20 63 1 1 21 64 1 0 22 65 1 1 23 66 1 0 24 67 1 1 25 68 1 0 26 69 1 6 27 70 1 0 28 71 1 6 29 72 1 0 34 73 1 0 37 74 1 0 37 75 1 0 37 76 1 0 40 77 1 0 40 78 1 0 40 79 1 0 41 80 1 0 44 81 1 0 45 82 1 0 47 83 1 0 M END

Standard InCHIKey	BFPKTWLXEAVKBG-KFKQZHGQSA-N
Standard InCHI	InChI=1S/C30H36O17/c1-10-18(32)22(36)24(38)29(44-10)43-9-16-19(33)23(37)25(39)30(46-16)47-28-21(35)17-14(8-15(41-3)27(42-4)20(17)34)45-26(28)11-5-6-12(31)13(7-11)40-2/h5-8,10,16,18-19,22-25,29-34,36-39H,9H2,1-4H3/t10-,16+,18-,19-,22+,23-,24+,25+,29+,30-/m0/s1
SMILES	COC1=CC(C2=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@H](O)[C@H](O)[C@H]3O)C(=O)C3=C(O)C(OC)=C(OC)C=C3O2)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	668.2	Volume:	612.996 ? Van der Waals volume.
Dense:	1.09	LogP:	0.678 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.197 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.232 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	256.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.135	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.806	Fsp³:	0.5
MCE-18:	124.0 ? 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:	0.587	Fluc inhibitor:	0.239 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.744 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.568 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.033	Promiscuous compounds:	0.36

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.18	MDCK Permeability:	-5.386
Pgp-inhibitor:	0.003	Pgp-substrate:	0.914
PAMPA:	0.989 ? 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):	0.895
20% Bioavailability (F20%):	0.267	30% Bioavailability (F30%):	0.853
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.583
Plasma Protein Binding (PPB):	83.999%	Volume Distribution (VD):	-0.088
Fu:	14.347% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.584
BSEP inhibitor:	0.058

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:	0.045
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.891
HLM stability:	0.238 ? 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):

1.431

Half-life (T1/2):

3.359

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.207
Human Hepatotoxicity (H-HT):	0.447	Drug-induced Liver Injury (DILI):	0.844
AMES Toxicity:	0.866	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.025	Skin Sensitization:	0.997
Carcinogencity:	0.057	Eye Corrosion:	0.0
Eye Irritation:	0.138	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.916
Hematotoxicity:	0.312	Drug-induced Nephrotoxicity:	0.599
Genotoxicity:	0.223	RPMI-8226 Immunitoxicity:	0.25
A549 Cytotoxicity:	0.629	Hek293 Cytotoxicity:	0.478
BCF:	0.419 ? 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:	4.478 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.699 ? 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
NPO24561	Sesuvium portulacastrum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24561	Sesuvium portulacastrum	Species	Aizoaceae	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 NPC584331 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	20504
0.1-0.2	25760
0.2-0.3	2650
0.3-0.4	534
0.4-0.5	263
0.5-0.6	100
0.6-0.7	35
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	Natural Product ID
0.7912	Intermediate Similarity	NPC476472
0.7912	Intermediate Similarity	NPC294815
0.7912	Intermediate Similarity	NPC16194
0.7363	Intermediate Similarity	NPC473571
0.7363	Intermediate Similarity	NPC110941
0.734	Intermediate Similarity	NPC473073
0.7283	Intermediate Similarity	NPC126784
0.7283	Intermediate Similarity	NPC241423
0.7204	Intermediate Similarity	NPC470443
0.7079	Intermediate Similarity	NPC488072
0.6897	Remote Similarity	NPC27640
0.6809	Remote Similarity	NPC186816
0.6598	Remote Similarity	NPC473327
0.6596	Remote Similarity	NPC173582
0.6596	Remote Similarity	NPC265885
0.6596	Remote Similarity	NPC181465
0.6596	Remote Similarity	NPC215710
0.6596	Remote Similarity	NPC473438
0.6596	Remote Similarity	NPC253788
0.6562	Remote Similarity	NPC153755
0.6542	Remote Similarity	NPC488079
0.6535	Remote Similarity	NPC89052
0.6526	Remote Similarity	NPC203259
0.6526	Remote Similarity	NPC65563
0.6526	Remote Similarity	NPC33054
0.6526	Remote Similarity	NPC470949
0.6526	Remote Similarity	NPC176740
0.6526	Remote Similarity	NPC471725
0.6526	Remote Similarity	NPC134532
0.6526	Remote Similarity	NPC602582
0.6458	Remote Similarity	NPC204693
0.6413	Remote Similarity	NPC223747
0.6408	Remote Similarity	NPC173837
0.6392	Remote Similarity	NPC488073
0.6311	Remote Similarity	NPC473072
0.6224	Remote Similarity	NPC488074
0.6154	Remote Similarity	NPC24043
0.6129	Remote Similarity	NPC101026
0.6129	Remote Similarity	NPC488077
0.6082	Remote Similarity	NPC39834
0.6078	Remote Similarity	NPC470449
0.6064	Remote Similarity	NPC99957
0.6019	Remote Similarity	NPC470446
0.6	Remote Similarity	NPC483414
0.6	Remote Similarity	NPC483415
0.598	Remote Similarity	NPC470447
0.5976	Remote Similarity	NPC261004
0.5941	Remote Similarity	NPC483416
0.5922	Remote Similarity	NPC470445
0.5882	Remote Similarity	NPC142142
0.5851	Remote Similarity	NPC488071
0.5841	Remote Similarity	NPC192539
0.5806	Remote Similarity	NPC305811
0.5806	Remote Similarity	NPC46420
0.5806	Remote Similarity	NPC271692
0.5804	Remote Similarity	NPC488078
0.5784	Remote Similarity	NPC209296
0.5758	Remote Similarity	NPC44931
0.5758	Remote Similarity	NPC67105
0.5741	Remote Similarity	NPC217520
0.57	Remote Similarity	NPC22062
0.57	Remote Similarity	NPC473634
0.57	Remote Similarity	NPC210073
0.57	Remote Similarity	NPC138811
0.57	Remote Similarity	NPC156869
0.567	Remote Similarity	NPC203050
0.567	Remote Similarity	NPC225434
0.566	Remote Similarity	NPC470455
0.5657	Remote Similarity	NPC471079
0.5638	Remote Similarity	NPC603655
0.5636	Remote Similarity	NPC139571
0.5612	Remote Similarity	NPC172807
0.56	Remote Similarity	NPC67326
0.5596	Remote Similarity	NPC480441
0.5596	Remote Similarity	NPC25523
0.5567	Remote Similarity	NPC602805
0.5556	Remote Similarity	NPC254540
0.5524	Remote Similarity	NPC220173
0.5521	Remote Similarity	NPC611303
0.55	Remote Similarity	NPC609888
0.5464	Remote Similarity	NPC21666
0.5463	Remote Similarity	NPC121703
0.5426	Remote Similarity	NPC249281
0.5413	Remote Similarity	NPC470451
0.5413	Remote Similarity	NPC470416
0.5413	Remote Similarity	NPC189564
0.5408	Remote Similarity	NPC206123
0.54	Remote Similarity	NPC473682
0.5392	Remote Similarity	NPC233994
0.5385	Remote Similarity	NPC12013
0.5385	Remote Similarity	NPC11432
0.5385	Remote Similarity	NPC477613
0.5368	Remote Similarity	NPC158674
0.5364	Remote Similarity	NPC292019
0.5364	Remote Similarity	NPC202908
0.5354	Remote Similarity	NPC276377
0.5347	Remote Similarity	NPC187379
0.5333	Remote Similarity	NPC122467
0.5333	Remote Similarity	NPC483707
0.5327	Remote Similarity	NPC36138
0.5321	Remote Similarity	NPC203145
0.53	Remote Similarity	NPC116864
0.53	Remote Similarity	NPC244776
0.53	Remote Similarity	NPC211594
0.5294	Remote Similarity	NPC227508
0.5288	Remote Similarity	NPC475366
0.5283	Remote Similarity	NPC486577
0.5278	Remote Similarity	NPC470450
0.5258	Remote Similarity	NPC59534
0.5238	Remote Similarity	NPC211532
0.5238	Remote Similarity	NPC488364
0.5234	Remote Similarity	NPC483412
0.5234	Remote Similarity	NPC89127
0.5204	Remote Similarity	NPC219904
0.5185	Remote Similarity	NPC221342
0.5185	Remote Similarity	NPC476470
0.5158	Remote Similarity	NPC111929
0.5158	Remote Similarity	NPC320283
0.5158	Remote Similarity	NPC41121
0.5155	Remote Similarity	NPC488080
0.5155	Remote Similarity	NPC169977
0.5152	Remote Similarity	NPC181616
0.5152	Remote Similarity	NPC606560
0.5138	Remote Similarity	NPC602448
0.5133	Remote Similarity	NPC277532
0.5104	Remote Similarity	NPC127546
0.5104	Remote Similarity	NPC57625
0.5104	Remote Similarity	NPC173637
0.5104	Remote Similarity	NPC317489
0.5104	Remote Similarity	NPC223424
0.5104	Remote Similarity	NPC600591
0.5102	Remote Similarity	NPC42773
0.5102	Remote Similarity	NPC45522
0.51	Remote Similarity	NPC116458
0.51	Remote Similarity	NPC246943
0.51	Remote Similarity	NPC605784
0.5096	Remote Similarity	NPC150164
0.5093	Remote Similarity	NPC473071
0.5093	Remote Similarity	NPC483413
0.5089	Remote Similarity	NPC477895
0.5085	Remote Similarity	NPC209550
0.5056	Remote Similarity	NPC469622
0.5052	Remote Similarity	NPC265530
0.5048	Remote Similarity	NPC470444
0.5047	Remote Similarity	NPC606657

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC584331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5430
0.1-0.2	3669
0.2-0.3	42
0.3-0.4	3
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
0.6526	Remote Similarity	NPD6797	Phase 2
0.6465	Remote Similarity	NPD7251	Phase 2
0.6373	Remote Similarity	NPD7808	Phase 3
0.5784	Remote Similarity	NPD7054	Phase 4
0.5182	Remote Similarity	NPD7472	Pre-clinical

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