NPASS Compound

Natural Product: NPC513929

Natural Product ID	NPC513929
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-7-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 77 81 0 0 0 0 0 0 0 0999 V2000 -9.5256 3.5497 2.1244 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2018 3.6835 2.5888 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2086 2.9229 1.9938 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4920 2.0388 0.9578 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5129 1.2689 0.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8468 0.4167 -0.6589 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1982 1.3734 0.7811 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2164 0.6211 0.1851 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4214 -0.1815 -0.7433 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8898 0.7465 0.6350 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9596 0.0058 0.0256 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3753 0.0780 -1.2119 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6937 -1.0993 -1.4763 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6669 -0.9857 -1.3963 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3534 -2.3491 -1.2969 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7455 -2.1259 -1.2300 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4302 -3.3157 -1.1218 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1674 -3.4507 0.0403 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2727 -2.6538 0.1274 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4543 -3.3421 0.7792 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1517 -3.7395 2.0905 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7217 -1.9881 -1.1219 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1862 -0.7012 -1.1858 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4921 -2.7703 -2.3699 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4642 -1.8359 -3.4299 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2467 -3.5794 -2.3632 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4677 -4.9413 -2.5739 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2005 -0.2129 -2.5684 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4851 0.3121 -2.2931 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2299 0.8937 -2.8876 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6916 0.5092 -3.8462 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5005 1.2360 -1.5682 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3880 1.7013 -0.6370 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6483 1.6072 1.6496 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3370 1.8059 2.2153 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0549 2.9270 3.0089 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1667 3.0743 3.6361 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1413 2.1342 3.5038 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3820 2.2905 4.1436 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9029 1.0205 2.7331 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9124 0.0785 2.6133 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3397 0.8959 2.1114 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6554 2.3341 2.2030 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8954 2.2407 1.8018 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8866 2.9949 2.3898 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5297 3.7025 1.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8781 2.5148 2.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1834 4.2875 2.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5228 1.9758 0.6466 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5717 0.6313 -1.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2652 0.2200 -1.9451 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0112 -0.4717 -0.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0216 -2.9094 -0.4209 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1369 -2.8868 -2.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6613 -4.1374 -1.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0004 -1.8259 0.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3143 -2.6474 0.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8036 -4.2097 0.1811 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5645 -3.0833 2.5426 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8361 -1.8220 -1.0309 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1630 -0.3625 -0.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3673 -3.4476 -2.5399 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0941 -0.9888 -3.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5914 -3.2370 -3.2169 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7698 -5.4081 -2.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3570 -0.8956 -3.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9102 0.6319 -3.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8302 1.7810 -3.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2898 0.4537 -4.7471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1058 2.1422 -1.8671 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6007 2.6528 -0.7937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8053 3.6790 3.1273 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3514 3.9588 4.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0114 1.4957 4.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7108 -0.9195 2.5587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4269 -0.0260 1.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6061 3.6632 3.1895 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 5 7 2 0 7 8 1 0 8 9 2 0 8 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 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 14 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 10 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 38 40 1 0 40 41 1 0 40 42 2 0 34 43 1 0 43 44 1 0 44 45 2 0 45 3 1 0 44 7 1 0 32 12 1 0 42 35 1 0 26 17 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 6 50 1 0 12 51 1 6 14 52 1 1 15 53 1 0 15 54 1 0 17 55 1 1 19 56 1 1 20 57 1 0 20 58 1 0 21 59 1 0 22 60 1 1 23 61 1 0 24 62 1 6 25 63 1 0 26 64 1 6 27 65 1 0 28 66 1 6 29 67 1 0 30 68 1 6 31 69 1 0 32 70 1 6 33 71 1 0 36 72 1 0 37 73 1 0 39 74 1 0 41 75 1 0 42 76 1 0 45 77 1 0 M END

Standard InCHIKey	VVNAVFMRGMPHSJ-XNMIZZHOSA-N
Standard InCHI	InChI=1S/C28H32O17/c1-40-10-5-13(32)17-14(6-10)42-25(9-2-3-11(30)12(31)4-9)26(20(17)35)45-28-24(39)22(37)19(34)16(44-28)8-41-27-23(38)21(36)18(33)15(7-29)43-27/h2-6,15-16,18-19,21-24,27-34,36-39H,7-8H2,1H3/t15-,16-,18-,19-,21-,22+,23+,24-,27+,28-/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C(O[C@@H]3O[C@@H](CO[C@@H]4O[C@@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)=C(C3=CC=C(O)C(O)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	640.16	Volume:	578.404 ? Van der Waals volume.
Dense:	1.107	LogP:	0.425 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.23 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.953 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	278.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.115	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.762	Fsp³:	0.464
MCE-18:	122.073 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.639	Fluc inhibitor:	0.28 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.883 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.62 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.096	Promiscuous compounds:	0.505

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.588	MDCK Permeability:	-5.177
Pgp-inhibitor:	0.0	Pgp-substrate:	0.124
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):	0.992
20% Bioavailability (F20%):	0.896	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.065
Plasma Protein Binding (PPB):	80.928%	Volume Distribution (VD):	-0.063
Fu:	17.694% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.806
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.028
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.198 ? 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):

1.954

Half-life (T1/2):

2.586

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.116
Human Hepatotoxicity (H-HT):	0.598	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.971	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.033	Skin Sensitization:	1.0
Carcinogencity:	0.123	Eye Corrosion:	0.0
Eye Irritation:	0.439	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.938
Hematotoxicity:	0.187	Drug-induced Nephrotoxicity:	0.457
Genotoxicity:	0.885	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.972	Hek293 Cytotoxicity:	0.448
BCF:	0.504 ? 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:	3.149 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.864 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.002 ? 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
NPO57520	Senna septemtrionalis	Species	Fabaceae	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 NPC513929 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	23089
0.1-0.2	22294
0.2-0.3	3199
0.3-0.4	705
0.4-0.5	268
0.5-0.6	102
0.6-0.7	78
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
0.8023	Intermediate Similarity	NPC488073
0.8	Intermediate Similarity	NPC156869
0.7975	Intermediate Similarity	NPC136042
0.7875	Intermediate Similarity	NPC84362
0.766	Intermediate Similarity	NPC480441
0.75	Intermediate Similarity	NPC186816
0.75	Intermediate Similarity	NPC605784
0.7439	Intermediate Similarity	NPC271692
0.7333	Intermediate Similarity	NPC470443
0.7174	Intermediate Similarity	NPC486577
0.7108	Intermediate Similarity	NPC297987
0.7079	Intermediate Similarity	NPC275454
0.7033	Intermediate Similarity	NPC126784
0.7033	Intermediate Similarity	NPC241423
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
0.6939	Remote Similarity	NPC25523
0.6889	Remote Similarity	NPC67326
0.6889	Remote Similarity	NPC67105
0.6875	Remote Similarity	NPC14187
0.686	Remote Similarity	NPC488071
0.6848	Remote Similarity	NPC488074
0.6837	Remote Similarity	NPC292019
0.6837	Remote Similarity	NPC202908
0.6813	Remote Similarity	NPC210073
0.6786	Remote Similarity	NPC289667
0.6737	Remote Similarity	NPC473073
0.6705	Remote Similarity	NPC116458
0.6705	Remote Similarity	NPC246943
0.6628	Remote Similarity	NPC46420
0.6552	Remote Similarity	NPC42773
0.6552	Remote Similarity	NPC45522
0.6535	Remote Similarity	NPC277532
0.6512	Remote Similarity	NPC145038
0.6512	Remote Similarity	NPC56077
0.6512	Remote Similarity	NPC281131
0.6512	Remote Similarity	NPC253662
0.6512	Remote Similarity	NPC179950
0.6512	Remote Similarity	NPC277205
0.6512	Remote Similarity	NPC158674
0.6512	Remote Similarity	NPC37919
0.6512	Remote Similarity	NPC88789
0.6512	Remote Similarity	NPC491374
0.6465	Remote Similarity	NPC121703
0.6458	Remote Similarity	NPC142142
0.6429	Remote Similarity	NPC470446
0.6421	Remote Similarity	NPC65711
0.6374	Remote Similarity	NPC116864
0.6374	Remote Similarity	NPC244776
0.6364	Remote Similarity	NPC599850
0.6344	Remote Similarity	NPC173582
0.6344	Remote Similarity	NPC265885
0.6344	Remote Similarity	NPC181465
0.6344	Remote Similarity	NPC215710
0.6344	Remote Similarity	NPC473438
0.6344	Remote Similarity	NPC253788
0.6322	Remote Similarity	NPC189142
0.6322	Remote Similarity	NPC77660
0.6304	Remote Similarity	NPC251417
0.6238	Remote Similarity	NPC189564
0.6237	Remote Similarity	NPC480466
0.6237	Remote Similarity	NPC471079
0.6224	Remote Similarity	NPC476472
0.6224	Remote Similarity	NPC294815
0.6224	Remote Similarity	NPC16194
0.6211	Remote Similarity	NPC473571
0.6211	Remote Similarity	NPC110941
0.6207	Remote Similarity	NPC249281
0.6186	Remote Similarity	NPC35119
0.6186	Remote Similarity	NPC473327
0.617	Remote Similarity	NPC44931
0.617	Remote Similarity	NPC39834
0.617	Remote Similarity	NPC227508
0.6168	Remote Similarity	NPC488078
0.6146	Remote Similarity	NPC240306
0.6146	Remote Similarity	NPC64425
0.6111	Remote Similarity	NPC611303
0.6105	Remote Similarity	NPC22062
0.6105	Remote Similarity	NPC479405
0.6105	Remote Similarity	NPC65563
0.6105	Remote Similarity	NPC473634
0.6105	Remote Similarity	NPC470949
0.6105	Remote Similarity	NPC138811
0.61	Remote Similarity	NPC135358
0.6087	Remote Similarity	NPC276377
0.6067	Remote Similarity	NPC24043
0.6067	Remote Similarity	NPC27640
0.6064	Remote Similarity	NPC29958
0.6042	Remote Similarity	NPC479404
0.602	Remote Similarity	NPC32641
0.602	Remote Similarity	NPC256188
0.602	Remote Similarity	NPC209296
0.6	Remote Similarity	NPC471748
0.6	Remote Similarity	NPC470445
0.5938	Remote Similarity	NPC150164
0.5918	Remote Similarity	NPC479403
0.5859	Remote Similarity	NPC229409
0.5843	Remote Similarity	NPC77672
0.5843	Remote Similarity	NPC133671
0.5843	Remote Similarity	NPC135391
0.5843	Remote Similarity	NPC78263
0.5843	Remote Similarity	NPC250069
0.5825	Remote Similarity	NPC203145
0.5824	Remote Similarity	NPC472459
0.5824	Remote Similarity	NPC59534
0.5795	Remote Similarity	NPC67037
0.5795	Remote Similarity	NPC255615
0.5778	Remote Similarity	NPC323593
0.5778	Remote Similarity	NPC203500
0.5773	Remote Similarity	NPC102028
0.5769	Remote Similarity	NPC470451
0.5769	Remote Similarity	NPC188871
0.5761	Remote Similarity	NPC175107
0.5745	Remote Similarity	NPC203050
0.5745	Remote Similarity	NPC488072
0.5745	Remote Similarity	NPC225434
0.5745	Remote Similarity	NPC601586
0.5743	Remote Similarity	NPC471669
0.5714	Remote Similarity	NPC305811
0.5714	Remote Similarity	NPC488080
0.5714	Remote Similarity	NPC169977
0.57	Remote Similarity	NPC122467
0.57	Remote Similarity	NPC37668
0.57	Remote Similarity	NPC473623
0.5699	Remote Similarity	NPC120099
0.5699	Remote Similarity	NPC486578
0.5686	Remote Similarity	NPC292929
0.5686	Remote Similarity	NPC470449
0.5684	Remote Similarity	NPC254855
0.5684	Remote Similarity	NPC94610
0.5684	Remote Similarity	NPC265115
0.5667	Remote Similarity	NPC127546
0.5667	Remote Similarity	NPC19388
0.5667	Remote Similarity	NPC240431
0.5667	Remote Similarity	NPC39360
0.5667	Remote Similarity	NPC57625
0.5667	Remote Similarity	NPC55786
0.5667	Remote Similarity	NPC29763
0.5667	Remote Similarity	NPC173637
0.5667	Remote Similarity	NPC210003
0.5667	Remote Similarity	NPC317489
0.5667	Remote Similarity	NPC238376
0.5667	Remote Similarity	NPC223424
0.5667	Remote Similarity	NPC600591
0.5657	Remote Similarity	NPC153755
0.5652	Remote Similarity	NPC117260
0.5644	Remote Similarity	NPC488089
0.5638	Remote Similarity	NPC311830
0.5631	Remote Similarity	NPC223426
0.5631	Remote Similarity	NPC602448
0.5625	Remote Similarity	NPC8856
0.5604	Remote Similarity	NPC64305
0.5604	Remote Similarity	NPC95090
0.5604	Remote Similarity	NPC27408
0.5588	Remote Similarity	NPC89127
0.5586	Remote Similarity	NPC470720
0.5577	Remote Similarity	NPC81042
0.5556	Remote Similarity	NPC223860
0.5556	Remote Similarity	NPC255157
0.5556	Remote Similarity	NPC259896
0.5545	Remote Similarity	NPC72016
0.5545	Remote Similarity	NPC606657
0.5543	Remote Similarity	NPC45638
0.5532	Remote Similarity	NPC101026
0.5532	Remote Similarity	NPC22832
0.5532	Remote Similarity	NPC21666
0.5532	Remote Similarity	NPC488077
0.5514	Remote Similarity	NPC164704
0.5495	Remote Similarity	NPC470719
0.5495	Remote Similarity	NPC19709
0.5495	Remote Similarity	NPC470717
0.5484	Remote Similarity	NPC325555
0.5484	Remote Similarity	NPC226304
0.5484	Remote Similarity	NPC201292
0.5474	Remote Similarity	NPC607707
0.5464	Remote Similarity	NPC254540
0.5464	Remote Similarity	NPC480463
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC295625
0.5455	Remote Similarity	NPC605592
0.5446	Remote Similarity	NPC483414
0.5446	Remote Similarity	NPC483415
0.5446	Remote Similarity	NPC488079
0.5426	Remote Similarity	NPC60735
0.5426	Remote Similarity	NPC26230
0.5426	Remote Similarity	NPC285197
0.5417	Remote Similarity	NPC190003
0.5413	Remote Similarity	NPC470716
0.5408	Remote Similarity	NPC139320
0.5408	Remote Similarity	NPC609888
0.5398	Remote Similarity	NPC209550
0.5392	Remote Similarity	NPC483416
0.5385	Remote Similarity	NPC101636
0.5376	Remote Similarity	NPC245014
0.537	Remote Similarity	NPC470715
0.537	Remote Similarity	NPC303694

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC513929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5666
0.1-0.2	3409
0.2-0.3	64
0.3-0.4	4
0.4-0.5	3
0.5-0.6	0
0.6-0.7	2
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8068	Intermediate Similarity	NPD7251	Phase 2
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6633	Remote Similarity	NPD7808	Phase 3
0.602	Remote Similarity	NPD7054	Phase 4

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