NPASS Compound

Natural Product: NPC522164

Natural Product ID	NPC522164
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-hydroxyphenyl)-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-hydroxyphenyl)-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 79 83 0 0 0 0 0 0 0 0999 V2000 -8.7732 -0.7299 1.3597 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9137 -0.1516 2.3264 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5565 0.0211 1.9827 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0772 -0.3593 0.7523 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7500 -0.2112 0.3628 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8760 0.3511 1.2747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3438 0.7431 2.5289 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4588 1.3055 3.4322 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6686 0.5791 2.8761 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1003 0.9799 4.1309 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5445 2.3085 4.3075 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5571 0.5146 0.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7152 1.0185 1.7248 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1388 0.0950 -0.3487 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7961 0.2676 -0.6673 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1514 -0.6371 -0.1339 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1504 0.0794 0.5346 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1337 -0.7093 1.0798 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8689 -0.0477 2.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5369 1.0970 1.9978 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6145 1.2283 1.2080 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7784 1.5554 2.0102 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9280 1.2725 1.2958 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4813 -0.0433 1.8194 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8170 1.3368 -0.1789 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0137 1.7988 -0.7802 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7138 2.1990 -0.7226 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1805 1.7142 -1.9243 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5938 2.4172 0.2496 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4004 2.6232 -0.3759 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8993 -1.3127 -0.0550 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0351 -0.3105 -1.0545 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9323 -2.3531 -0.6545 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5047 -3.0714 -1.6786 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6405 -1.6595 -1.0699 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3248 -2.6693 -1.3242 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0370 -0.4475 -1.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7188 -0.8969 -2.5575 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6518 -1.7187 -3.2160 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4658 -2.1372 -4.5157 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3412 -1.7618 -5.2369 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1617 -2.1875 -6.5454 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4204 -0.9593 -4.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6293 -0.5418 -3.2785 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3055 -0.5665 -0.7867 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7946 -0.8994 1.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3815 -1.6549 0.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9254 -0.0055 0.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7457 -0.8031 0.0179 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6103 1.3144 4.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3744 2.3944 5.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6466 2.8953 4.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8472 2.7113 3.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3989 -1.2070 0.6857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5687 -1.5995 1.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1289 0.0174 3.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6011 -0.8219 2.5980 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9470 0.3235 0.6654 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6835 2.0515 1.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8797 -0.4081 2.7051 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5171 0.0474 2.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4737 -0.8514 1.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6719 0.3109 -0.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8134 2.1695 -1.6687 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1240 3.2182 -0.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3512 0.7551 -2.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8512 3.3556 0.8200 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4882 2.4167 -1.3249 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8471 -1.7534 0.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2290 0.2322 -1.1305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -3.0392 0.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9240 -3.0374 -2.4696 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8718 -1.2096 -2.0504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9777 -2.6531 -0.5808 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5298 -2.0123 -2.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1772 -2.7702 -5.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8863 -3.1150 -6.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5272 -0.6492 -5.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8813 0.1060 -2.8446 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 1 0 7 9 2 0 9 10 1 0 10 11 1 0 6 12 1 0 12 13 2 0 12 14 1 0 14 15 1 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 23 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 18 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 14 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 41 43 1 0 43 44 2 0 37 45 1 0 9 3 1 0 35 16 1 0 44 38 1 0 45 5 1 0 29 21 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 8 50 1 0 11 51 1 0 11 52 1 0 11 53 1 0 16 54 1 1 18 55 1 1 19 56 1 0 19 57 1 0 21 58 1 6 23 59 1 1 24 60 1 0 24 61 1 0 24 62 1 0 25 63 1 6 26 64 1 0 27 65 1 6 28 66 1 0 29 67 1 1 30 68 1 0 31 69 1 1 32 70 1 0 33 71 1 1 34 72 1 0 35 73 1 6 36 74 1 0 39 75 1 0 40 76 1 0 42 77 1 0 43 78 1 0 44 79 1 0 M END

Standard InCHIKey	MJXUYBKVKAWSGM-JRSLIQOASA-N
Standard InCHI	InChI=1S/C29H34O16/c1-10-17(31)21(35)23(37)28(42-10)41-9-15-18(32)22(36)24(38)29(44-15)45-27-20(34)16-13(8-14(39-2)26(40-3)19(16)33)43-25(27)11-4-6-12(30)7-5-11/h4-8,10,15,17-18,21-24,28-33,35-38H,9H2,1-3H3/t10-,15+,17-,18-,21+,22-,23+,24+,28+,29-/m0/s1
SMILES	COC1=CC2=C(C(O)=C1OC)C(=O)C(O[C@@H]1O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H](O)[C@H]1O)=C(C1=CC=C(O)C=C1)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.18	Volume:	586.91 ? Van der Waals volume.
Dense:	1.087	LogP:	0.723 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.159 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.514 ? 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:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.734	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:	0.571	Fluc inhibitor:	0.221 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.712 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.55 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.04	Promiscuous compounds:	0.323

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.247	MDCK Permeability:	-5.353
Pgp-inhibitor:	0.001	Pgp-substrate:	0.965
PAMPA:	0.999 ? 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):	0.491
20% Bioavailability (F20%):	0.252	30% Bioavailability (F30%):	0.844
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.54
Plasma Protein Binding (PPB):	85.069%	Volume Distribution (VD):	-0.004
Fu:	12.831% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.971
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.165
BSEP inhibitor:	0.027

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:	0.031
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.911
HLM stability:	0.422 ? 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):

1.512

Half-life (T1/2):

3.129

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.214
Human Hepatotoxicity (H-HT):	0.459	Drug-induced Liver Injury (DILI):	0.836
AMES Toxicity:	0.847	Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.04	Skin Sensitization:	0.996
Carcinogencity:	0.069	Eye Corrosion:	0.0
Eye Irritation:	0.196	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.9
Hematotoxicity:	0.207	Drug-induced Nephrotoxicity:	0.409
Genotoxicity:	0.561	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.59	Hek293 Cytotoxicity:	0.632
BCF:	0.415 ? 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:	3.007 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.579 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.682 ? 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 NPC522164 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	19239
0.1-0.2	26678
0.2-0.3	2959
0.3-0.4	519
0.4-0.5	260
0.5-0.6	135
0.6-0.7	42
0.7-0.8	1
0.8-0.85	2
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	NPC473571
0.8333	Intermediate Similarity	NPC110941
0.7907	Intermediate Similarity	NPC186816
0.7674	Intermediate Similarity	NPC173582
0.7674	Intermediate Similarity	NPC265885
0.7674	Intermediate Similarity	NPC181465
0.7674	Intermediate Similarity	NPC215710
0.7674	Intermediate Similarity	NPC473438
0.7674	Intermediate Similarity	NPC253788
0.7667	Intermediate Similarity	NPC473073
0.7586	Intermediate Similarity	NPC65563
0.7586	Intermediate Similarity	NPC470949
0.7416	Intermediate Similarity	NPC126784
0.7416	Intermediate Similarity	NPC241423
0.7333	Intermediate Similarity	NPC470443
0.7229	Intermediate Similarity	NPC24043
0.7229	Intermediate Similarity	NPC27640
0.7	Intermediate Similarity	NPC203259
0.7	Intermediate Similarity	NPC33054
0.7	Intermediate Similarity	NPC176740
0.7	Intermediate Similarity	NPC471725
0.7	Intermediate Similarity	NPC134532
0.7	Intermediate Similarity	NPC602582
0.6915	Remote Similarity	NPC476472
0.6915	Remote Similarity	NPC294815
0.6915	Remote Similarity	NPC16194
0.6842	Remote Similarity	NPC470449
0.6824	Remote Similarity	NPC46420
0.6809	Remote Similarity	NPC142142
0.6739	Remote Similarity	NPC204693
0.6737	Remote Similarity	NPC470447
0.6702	Remote Similarity	NPC473327
0.6593	Remote Similarity	NPC471079
0.6522	Remote Similarity	NPC44931
0.6522	Remote Similarity	NPC39834
0.6489	Remote Similarity	NPC488073
0.6489	Remote Similarity	NPC488074
0.6436	Remote Similarity	NPC25523
0.6395	Remote Similarity	NPC249281
0.6374	Remote Similarity	NPC172807
0.6364	Remote Similarity	NPC470455
0.6333	Remote Similarity	NPC99957
0.6304	Remote Similarity	NPC473682
0.6264	Remote Similarity	NPC276377
0.625	Remote Similarity	NPC12013
0.625	Remote Similarity	NPC483414
0.625	Remote Similarity	NPC11432
0.625	Remote Similarity	NPC483415
0.625	Remote Similarity	NPC477613
0.6238	Remote Similarity	NPC189564
0.6186	Remote Similarity	NPC483416
0.6139	Remote Similarity	NPC203145
0.6111	Remote Similarity	NPC488071
0.6105	Remote Similarity	NPC156869
0.61	Remote Similarity	NPC470446
0.6092	Remote Similarity	NPC111929
0.6092	Remote Similarity	NPC320283
0.6092	Remote Similarity	NPC41121
0.6067	Remote Similarity	NPC271692
0.6	Remote Similarity	NPC67326
0.6	Remote Similarity	NPC36138
0.6	Remote Similarity	NPC67105
0.6	Remote Similarity	NPC221342
0.6	Remote Similarity	NPC470445
0.6	Remote Similarity	NPC476470
0.598	Remote Similarity	NPC121703
0.5978	Remote Similarity	NPC116458
0.5978	Remote Similarity	NPC246943
0.5941	Remote Similarity	NPC470450
0.5941	Remote Similarity	NPC602448
0.5938	Remote Similarity	NPC22062
0.5938	Remote Similarity	NPC473634
0.5938	Remote Similarity	NPC210073
0.5938	Remote Similarity	NPC138811
0.5938	Remote Similarity	NPC150164
0.5914	Remote Similarity	NPC488072
0.5889	Remote Similarity	NPC305811
0.5889	Remote Similarity	NPC488080
0.5889	Remote Similarity	NPC169977
0.5816	Remote Similarity	NPC240306
0.581	Remote Similarity	NPC480441
0.5789	Remote Similarity	NPC254540
0.5769	Remote Similarity	NPC470416
0.5769	Remote Similarity	NPC101830
0.5729	Remote Similarity	NPC187379
0.5714	Remote Similarity	NPC292019
0.5714	Remote Similarity	NPC129264
0.5714	Remote Similarity	NPC202908
0.5714	Remote Similarity	NPC470444
0.57	Remote Similarity	NPC122467
0.57	Remote Similarity	NPC32641
0.57	Remote Similarity	NPC256188
0.57	Remote Similarity	NPC209296
0.57	Remote Similarity	NPC72016
0.5684	Remote Similarity	NPC116864
0.5684	Remote Similarity	NPC244776
0.5673	Remote Similarity	NPC89052
0.5657	Remote Similarity	NPC153755
0.5612	Remote Similarity	NPC233994
0.5612	Remote Similarity	NPC303913
0.5604	Remote Similarity	NPC297987
0.5604	Remote Similarity	NPC158674
0.5588	Remote Similarity	NPC89127
0.5586	Remote Similarity	NPC488079
0.5586	Remote Similarity	NPC488078
0.5566	Remote Similarity	NPC173837
0.5545	Remote Similarity	NPC270448
0.5545	Remote Similarity	NPC483707
0.5545	Remote Similarity	NPC35119
0.5536	Remote Similarity	NPC209550
0.5521	Remote Similarity	NPC211594
0.5517	Remote Similarity	NPC483159
0.5517	Remote Similarity	NPC483160
0.551	Remote Similarity	NPC227508
0.55	Remote Similarity	NPC470125
0.5495	Remote Similarity	NPC127546
0.5495	Remote Similarity	NPC57625
0.5495	Remote Similarity	NPC173637
0.5495	Remote Similarity	NPC317489
0.5495	Remote Similarity	NPC223424
0.5495	Remote Similarity	NPC600591
0.549	Remote Similarity	NPC486577
0.5474	Remote Similarity	NPC223747
0.5472	Remote Similarity	NPC470451
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC129827
0.5446	Remote Similarity	NPC211532
0.5446	Remote Similarity	NPC488364
0.5437	Remote Similarity	NPC85751
0.5437	Remote Similarity	NPC19240
0.5437	Remote Similarity	NPC483412
0.5435	Remote Similarity	NPC93337
0.5426	Remote Similarity	NPC611303
0.5417	Remote Similarity	NPC476215
0.5408	Remote Similarity	NPC609888
0.5385	Remote Similarity	NPC101636
0.5385	Remote Similarity	NPC473554
0.5376	Remote Similarity	NPC105025
0.5376	Remote Similarity	NPC603655
0.5368	Remote Similarity	NPC21666
0.5357	Remote Similarity	NPC474522
0.5347	Remote Similarity	NPC475366
0.5327	Remote Similarity	NPC473072
0.5326	Remote Similarity	NPC77672
0.5326	Remote Similarity	NPC133671
0.5326	Remote Similarity	NPC135391
0.5326	Remote Similarity	NPC78263
0.5326	Remote Similarity	NPC250069
0.5321	Remote Similarity	NPC277532
0.5319	Remote Similarity	NPC59534
0.5312	Remote Similarity	NPC605784
0.5294	Remote Similarity	NPC469622
0.5288	Remote Similarity	NPC473071
0.5288	Remote Similarity	NPC483413
0.5283	Remote Similarity	NPC214621
0.5283	Remote Similarity	NPC34267
0.5269	Remote Similarity	NPC265530
0.5263	Remote Similarity	NPC138990
0.5263	Remote Similarity	NPC219904
0.5263	Remote Similarity	NPC241781
0.5258	Remote Similarity	NPC66087
0.5238	Remote Similarity	NPC292929
0.5229	Remote Similarity	NPC303694
0.5217	Remote Similarity	NPC192539
0.5217	Remote Similarity	NPC114740
0.5208	Remote Similarity	NPC181616
0.5204	Remote Similarity	NPC265115
0.5204	Remote Similarity	NPC477848
0.52	Remote Similarity	NPC163242
0.52	Remote Similarity	NPC272068
0.5161	Remote Similarity	NPC108831
0.5161	Remote Similarity	NPC182634
0.5158	Remote Similarity	NPC42773
0.5158	Remote Similarity	NPC45522
0.5149	Remote Similarity	NPC475155
0.5149	Remote Similarity	NPC605592
0.5143	Remote Similarity	NPC471669
0.514	Remote Similarity	NPC14187
0.5138	Remote Similarity	NPC477895
0.5133	Remote Similarity	NPC480445
0.51	Remote Similarity	NPC139320
0.5096	Remote Similarity	NPC37668
0.5091	Remote Similarity	NPC217520
0.5088	Remote Similarity	NPC156785
0.5088	Remote Similarity	NPC162394
0.5086	Remote Similarity	NPC175429
0.5055	Remote Similarity	NPC54802
0.5055	Remote Similarity	NPC197304
0.5054	Remote Similarity	NPC135599
0.5054	Remote Similarity	NPC73855
0.5054	Remote Similarity	NPC331652
0.5054	Remote Similarity	NPC113968
0.5054	Remote Similarity	NPC328940
0.5054	Remote Similarity	NPC277174
0.5054	Remote Similarity	NPC606877
0.5052	Remote Similarity	NPC101026
0.5052	Remote Similarity	NPC488077
0.5049	Remote Similarity	NPC296018
0.5049	Remote Similarity	NPC64425
0.5047	Remote Similarity	NPC223426

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC522164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5195
0.1-0.2	3895
0.2-0.3	51
0.3-0.4	3
0.4-0.5	1
0.5-0.6	2
0.6-0.7	2
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
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6737	Remote Similarity	NPD7251	Phase 2
0.63	Remote Similarity	NPD7808	Phase 3
0.57	Remote Similarity	NPD7054	Phase 4
0.5093	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