NPASS Compound

Natural Product: NPC549892

Natural Product ID	NPC549892
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dihydroxyphenyl)-5-hydroxy-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	2-(3,4-dihydroxyphenyl)-5-hydroxy-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 80 84 0 0 0 0 0 0 0 0999 V2000 -6.6711 5.1175 0.0481 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5935 4.9186 -0.7987 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7755 3.8109 -0.8846 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9069 2.6743 -0.1170 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0642 1.5804 -0.2341 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0384 1.6336 -1.1701 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8776 2.7556 -1.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8532 2.8113 -2.8919 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7470 3.8306 -1.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5971 4.9667 -2.5852 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3024 4.9934 -3.8219 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1991 0.5496 -1.2884 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2575 0.5559 -2.1217 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3820 -0.5950 -0.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4620 -1.6333 -0.6749 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1915 -1.5821 0.0100 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6496 -0.9781 -0.9503 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0037 -1.2178 -0.7279 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7514 -0.5706 -1.8694 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1111 -0.6634 -1.8390 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7590 -0.0745 -0.7783 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4758 1.0181 -1.3376 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1094 1.7812 -0.3868 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1648 2.5767 0.4828 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0891 0.9810 0.4505 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1546 0.6175 -0.3693 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4744 -0.2720 0.9966 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6122 -0.0597 2.0414 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7978 -0.9655 -0.1913 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3833 -2.1856 0.2588 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3141 -2.7043 -0.8199 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1118 -3.0445 -1.8793 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0209 -3.5123 -0.7893 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3299 -3.2752 -1.9463 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2519 -2.9153 0.4066 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1220 -2.9091 1.5169 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4035 -0.5701 0.4087 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6852 -1.7020 1.2931 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2450 -2.9718 1.1510 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5388 -3.9416 2.1009 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2875 -3.6423 3.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5702 -4.6379 4.1577 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7525 -2.3627 3.3894 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5154 -2.0219 4.5044 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4476 -1.4210 2.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1787 0.5069 0.4788 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5833 6.0336 0.6766 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5669 5.3216 -0.6121 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9444 4.2157 0.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7002 2.6183 0.6161 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9127 3.1293 -2.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3910 4.9008 -3.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0446 5.8749 -4.4193 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0567 4.1051 -4.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3349 -0.8950 0.8631 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3280 -0.7487 0.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4209 0.5087 -1.9802 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4135 -1.0552 -2.8232 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0120 0.3382 -0.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7324 2.5203 -0.9377 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3100 2.3452 1.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1296 2.3622 0.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3064 3.6868 0.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4208 1.5980 1.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4044 -0.3283 -0.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2787 -0.9576 1.3286 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6725 0.0322 1.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6144 -1.0438 -0.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0320 -2.8722 -0.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8294 -2.9766 0.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6242 -3.2112 -2.7276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2087 -4.5845 -0.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0218 -4.1117 -2.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5246 -3.6105 0.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4894 -3.8431 1.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6945 -3.2183 0.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -4.9442 1.9447 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4940 -4.7982 4.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1291 -1.2334 4.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8069 -0.4087 2.5587 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 1 0 43 45 2 0 37 46 1 0 9 3 1 0 35 16 1 0 45 38 1 0 46 5 1 0 29 21 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 8 51 1 0 11 52 1 0 11 53 1 0 11 54 1 0 16 55 1 1 18 56 1 1 19 57 1 0 19 58 1 0 21 59 1 1 23 60 1 6 24 61 1 0 24 62 1 0 24 63 1 0 25 64 1 1 26 65 1 0 27 66 1 1 28 67 1 0 29 68 1 6 30 69 1 0 31 70 1 1 32 71 1 0 33 72 1 1 34 73 1 0 35 74 1 1 36 75 1 0 39 76 1 0 40 77 1 0 42 78 1 0 44 79 1 0 45 80 1 0 M END

Standard InCHIKey	USZQOCYTRJLIOF-JRHXFWIGSA-N
Standard InCHI	InChI=1S/C29H34O17/c1-9-17(32)21(36)23(38)28(43-9)42-8-15-18(33)22(37)24(39)29(45-15)46-27-20(35)16-13(7-14(40-2)26(41-3)19(16)34)44-25(27)10-4-5-11(30)12(31)6-10/h4-7,9,15,17-18,21-24,28-34,36-39H,8H2,1-3H3/t9-,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(O)=C1)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.18	Volume:	595.7 ? Van der Waals volume.
Dense:	1.098	LogP:	0.454 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.026 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.182 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	267.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.127	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.833	Fsp³:	0.483
MCE-18:	124.744 ? 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:	1
Colloidal aggregators:	0.592	Fluc inhibitor:	0.251 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.784 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.582 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.049	Promiscuous compounds:	0.442

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.272	MDCK Permeability:	-5.412
Pgp-inhibitor:	0.0	Pgp-substrate:	0.759
PAMPA:	0.998 ? 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):	0.872
20% Bioavailability (F20%):	0.861	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.612
Plasma Protein Binding (PPB):	82.912%	Volume Distribution (VD):	-0.059
Fu:	15.514% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.981
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.098
BSEP inhibitor:	0.002

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:	0.027
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.751
HLM stability:	0.424 ? 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):

1.821

Half-life (T1/2):

3.529

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.268
Human Hepatotoxicity (H-HT):	0.402	Drug-induced Liver Injury (DILI):	0.88
AMES Toxicity:	0.866	Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	0.999
Carcinogencity:	0.041	Eye Corrosion:	0.0
Eye Irritation:	0.216	Respiratory Toxicity:	0.009
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.96
Hematotoxicity:	0.155	Drug-induced Nephrotoxicity:	0.283
Genotoxicity:	0.514	RPMI-8226 Immunitoxicity:	0.097
A549 Cytotoxicity:	0.86	Hek293 Cytotoxicity:	0.398
BCF:	0.489 ? 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:	3.16 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.753 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.906 ? 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 NPC549892 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	20199
0.1-0.2	25949
0.2-0.3	2773
0.3-0.4	482
0.4-0.5	246
0.5-0.6	125
0.6-0.7	51
0.7-0.8	2
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
0.8605	High Similarity	NPC473073
0.8353	Intermediate Similarity	NPC126784
0.8353	Intermediate Similarity	NPC241423
0.8256	Intermediate Similarity	NPC470443
0.8228	Intermediate Similarity	NPC27640
0.7701	Intermediate Similarity	NPC203259
0.7701	Intermediate Similarity	NPC33054
0.7701	Intermediate Similarity	NPC176740
0.7701	Intermediate Similarity	NPC471725
0.7701	Intermediate Similarity	NPC134532
0.7701	Intermediate Similarity	NPC602582
0.7416	Intermediate Similarity	NPC473571
0.7416	Intermediate Similarity	NPC110941
0.7333	Intermediate Similarity	NPC488073
0.7222	Intermediate Similarity	NPC186816
0.7143	Intermediate Similarity	NPC488074
0.7065	Intermediate Similarity	NPC483414
0.7065	Intermediate Similarity	NPC483415
0.7	Intermediate Similarity	NPC173582
0.7	Intermediate Similarity	NPC265885
0.7	Intermediate Similarity	NPC181465
0.7	Intermediate Similarity	NPC215710
0.7	Intermediate Similarity	NPC473438
0.7	Intermediate Similarity	NPC253788
0.6989	Remote Similarity	NPC483416
0.6977	Remote Similarity	NPC488071
0.6941	Remote Similarity	NPC271692
0.6923	Remote Similarity	NPC65563
0.6923	Remote Similarity	NPC470949
0.6875	Remote Similarity	NPC470446
0.6842	Remote Similarity	NPC476472
0.6842	Remote Similarity	NPC294815
0.6842	Remote Similarity	NPC16194
0.6813	Remote Similarity	NPC39834
0.6809	Remote Similarity	NPC473327
0.6771	Remote Similarity	NPC470445
0.6744	Remote Similarity	NPC305811
0.6739	Remote Similarity	NPC156869
0.6667	Remote Similarity	NPC204693
0.663	Remote Similarity	NPC67326
0.663	Remote Similarity	NPC67105
0.6559	Remote Similarity	NPC210073
0.6535	Remote Similarity	NPC480441
0.6413	Remote Similarity	NPC254540
0.6364	Remote Similarity	NPC24043
0.6304	Remote Similarity	NPC116864
0.6304	Remote Similarity	NPC244776
0.6289	Remote Similarity	NPC122467
0.6275	Remote Similarity	NPC292019
0.6275	Remote Similarity	NPC202908
0.6264	Remote Similarity	NPC99957
0.6262	Remote Similarity	NPC488078
0.6224	Remote Similarity	NPC142142
0.6224	Remote Similarity	NPC486577
0.6211	Remote Similarity	NPC233994
0.618	Remote Similarity	NPC46420
0.6176	Remote Similarity	NPC470451
0.6162	Remote Similarity	NPC483412
0.6162	Remote Similarity	NPC89127
0.6136	Remote Similarity	NPC127546
0.6136	Remote Similarity	NPC57625
0.6136	Remote Similarity	NPC173637
0.6136	Remote Similarity	NPC317489
0.6136	Remote Similarity	NPC223424
0.6136	Remote Similarity	NPC600591
0.6111	Remote Similarity	NPC59534
0.61	Remote Similarity	NPC470449
0.6087	Remote Similarity	NPC605784
0.6067	Remote Similarity	NPC158674
0.602	Remote Similarity	NPC211532
0.602	Remote Similarity	NPC488364
0.6	Remote Similarity	NPC470447
0.6	Remote Similarity	NPC471079
0.6	Remote Similarity	NPC473071
0.6	Remote Similarity	NPC483413
0.5957	Remote Similarity	NPC265115
0.5938	Remote Similarity	NPC44931
0.5938	Remote Similarity	NPC227508
0.5934	Remote Similarity	NPC42773
0.5934	Remote Similarity	NPC45522
0.5905	Remote Similarity	NPC25523
0.5876	Remote Similarity	NPC22062
0.5876	Remote Similarity	NPC473634
0.5876	Remote Similarity	NPC138811
0.5851	Remote Similarity	NPC488072
0.5825	Remote Similarity	NPC14187
0.5823	Remote Similarity	NPC18772
0.58	Remote Similarity	NPC209296
0.5789	Remote Similarity	NPC172807
0.5778	Remote Similarity	NPC249281
0.5755	Remote Similarity	NPC303694
0.5714	Remote Similarity	NPC136042
0.5714	Remote Similarity	NPC189564
0.5714	Remote Similarity	NPC605592
0.57	Remote Similarity	NPC12013
0.57	Remote Similarity	NPC11432
0.57	Remote Similarity	NPC477613
0.5699	Remote Similarity	NPC611303
0.5686	Remote Similarity	NPC471669
0.5684	Remote Similarity	NPC276377
0.5673	Remote Similarity	NPC470455
0.567	Remote Similarity	NPC480466
0.5652	Remote Similarity	NPC84362
0.5644	Remote Similarity	NPC37668
0.5638	Remote Similarity	NPC21666
0.5625	Remote Similarity	NPC241781
0.5619	Remote Similarity	NPC89052
0.5619	Remote Similarity	NPC203145
0.56	Remote Similarity	NPC153755
0.5591	Remote Similarity	NPC117260
0.5567	Remote Similarity	NPC473682
0.5536	Remote Similarity	NPC488079
0.5532	Remote Similarity	NPC175107
0.5514	Remote Similarity	NPC173837
0.551	Remote Similarity	NPC187379
0.5495	Remote Similarity	NPC111929
0.5495	Remote Similarity	NPC320283
0.5495	Remote Similarity	NPC41121
0.549	Remote Similarity	NPC483707
0.5484	Remote Similarity	NPC45638
0.5481	Remote Similarity	NPC221342
0.5481	Remote Similarity	NPC476470
0.5472	Remote Similarity	NPC121703
0.5464	Remote Similarity	NPC95866
0.5464	Remote Similarity	NPC211594
0.5446	Remote Similarity	NPC156785
0.5446	Remote Similarity	NPC162394
0.5446	Remote Similarity	NPC475366
0.5429	Remote Similarity	NPC223426
0.5429	Remote Similarity	NPC602448
0.5426	Remote Similarity	NPC201292
0.5426	Remote Similarity	NPC599850
0.5417	Remote Similarity	NPC223747
0.5417	Remote Similarity	NPC116458
0.5417	Remote Similarity	NPC246943
0.54	Remote Similarity	NPC150164
0.5377	Remote Similarity	NPC81042
0.5376	Remote Similarity	NPC145038
0.5376	Remote Similarity	NPC56077
0.5376	Remote Similarity	NPC281131
0.5376	Remote Similarity	NPC253662
0.5376	Remote Similarity	NPC179950
0.5376	Remote Similarity	NPC88789
0.5376	Remote Similarity	NPC491374
0.5368	Remote Similarity	NPC219904
0.5354	Remote Similarity	NPC609888
0.5333	Remote Similarity	NPC36138
0.5326	Remote Similarity	NPC135599
0.5326	Remote Similarity	NPC73855
0.5326	Remote Similarity	NPC113968
0.5326	Remote Similarity	NPC328940
0.5326	Remote Similarity	NPC277174
0.5326	Remote Similarity	NPC606877
0.5319	Remote Similarity	NPC349108
0.5319	Remote Similarity	NPC603655
0.5294	Remote Similarity	NPC240306
0.5283	Remote Similarity	NPC470450
0.5278	Remote Similarity	NPC473072
0.5269	Remote Similarity	NPC238376
0.5248	Remote Similarity	NPC155877
0.5243	Remote Similarity	NPC65711
0.5213	Remote Similarity	NPC265530
0.5204	Remote Similarity	NPC355481
0.5196	Remote Similarity	NPC129264
0.5192	Remote Similarity	NPC32641
0.5192	Remote Similarity	NPC256188
0.5192	Remote Similarity	NPC270448
0.5192	Remote Similarity	NPC72016
0.5192	Remote Similarity	NPC606657
0.5172	Remote Similarity	NPC192539
0.5161	Remote Similarity	NPC114740
0.5158	Remote Similarity	NPC488080
0.5158	Remote Similarity	NPC169977
0.5155	Remote Similarity	NPC181616
0.5149	Remote Similarity	NPC471748
0.5149	Remote Similarity	NPC275454
0.5146	Remote Similarity	NPC154741
0.5143	Remote Similarity	NPC64755
0.5138	Remote Similarity	NPC470416
0.5135	Remote Similarity	NPC277532
0.513	Remote Similarity	NPC480444
0.5126	Remote Similarity	NPC487499
0.5118	Remote Similarity	NPC482520
0.5118	Remote Similarity	NPC482521
0.5118	Remote Similarity	NPC482519
0.5109	Remote Similarity	NPC276222
0.5109	Remote Similarity	NPC274618
0.5109	Remote Similarity	NPC118284
0.5109	Remote Similarity	NPC608147
0.5106	Remote Similarity	NPC19709
0.51	Remote Similarity	NPC251417
0.5098	Remote Similarity	NPC473512
0.5098	Remote Similarity	NPC475155
0.5098	Remote Similarity	NPC303913
0.5086	Remote Similarity	NPC209550
0.5057	Remote Similarity	NPC469622
0.5054	Remote Similarity	NPC67037
0.5054	Remote Similarity	NPC255615
0.5053	Remote Similarity	NPC297987
0.505	Remote Similarity	NPC29958

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC549892 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5327
0.1-0.2	3770
0.2-0.3	44
0.3-0.4	3
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	2
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
0.7701	Intermediate Similarity	NPD6797	Phase 2
0.7582	Intermediate Similarity	NPD7251	Phase 2
0.64	Remote Similarity	NPD7808	Phase 3
0.58	Remote Similarity	NPD7054	Phase 4
0.5185	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