NPASS Compound

Natural Product: NPC571492

Natural Product ID	NPC571492
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)-3-hydroxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-3-hydroxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{R})-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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 72 76 0 0 0 0 0 0 0 0999 V2000 -7.7922 1.1927 2.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2309 1.6738 1.0111 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0267 1.0407 0.8389 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3111 1.4782 -0.2736 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4667 0.4653 -0.6513 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1163 0.7705 -0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3971 -0.5083 -1.0587 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0471 -0.3920 -1.0648 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3591 -1.1747 -0.1595 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8895 -0.6308 0.0537 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1328 -1.1296 -0.2355 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3464 -2.3525 -0.8338 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6554 -2.7292 -1.0668 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7176 -1.9062 -0.7114 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0232 -2.2653 -0.9359 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2822 -3.3621 -1.4752 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0468 -1.3826 -0.5503 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3459 -1.7795 -0.7928 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7895 -0.1801 0.0401 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7930 0.7998 0.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3531 1.9911 1.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2314 2.9522 1.4987 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5911 2.7586 1.3471 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4974 3.7177 1.7738 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0775 1.6082 0.7686 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4454 1.3795 0.5996 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1397 0.6686 0.3527 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5086 0.0992 0.2251 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5189 -0.6813 -0.1126 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2027 -0.3102 0.1179 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1420 -1.4142 1.1126 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3196 -2.1312 1.9813 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2882 -2.3174 0.7169 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1272 -2.5723 1.8030 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -1.7256 -0.4441 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1993 -2.7480 -1.4011 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3075 1.8501 -1.3487 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6514 3.1914 -1.1905 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5419 0.9803 -1.3107 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1130 -0.3391 -1.4339 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2693 1.2431 -0.0287 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8142 0.0068 0.3895 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8345 0.0780 2.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1108 1.4654 3.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8313 1.5974 2.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1579 2.7742 1.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7842 2.4160 0.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8680 1.6167 -1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7794 1.0801 0.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6973 -0.5580 -2.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2562 -2.1697 -0.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5081 -2.9773 -1.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8550 -3.6877 -1.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8129 -2.5429 -0.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2802 2.1142 1.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8750 3.8747 1.9612 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0329 4.2572 1.0996 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0580 2.1146 0.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5535 -0.2109 -0.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0378 0.6645 0.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4573 -0.5113 1.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2741 -3.0804 1.7359 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8020 -3.2796 0.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7509 -3.3093 1.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0463 -1.4997 -0.0919 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4513 -3.5511 -0.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8788 1.7498 -2.3655 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8802 3.6970 -0.8207 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1750 1.2215 -2.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8902 -0.7012 -0.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0615 2.0070 -0.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1017 -0.4850 -0.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 17 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 2 0 19 28 1 0 28 29 1 0 29 30 2 0 9 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 4 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 2 1 0 35 7 1 0 30 11 1 0 29 14 1 0 27 20 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 4 47 1 1 6 48 1 0 6 49 1 0 7 50 1 6 9 51 1 6 12 52 1 0 13 53 1 0 18 54 1 0 21 55 1 0 22 56 1 0 24 57 1 0 26 58 1 0 27 59 1 0 30 60 1 0 31 61 1 1 32 62 1 0 33 63 1 6 34 64 1 0 35 65 1 1 36 66 1 0 37 67 1 6 38 68 1 0 39 69 1 6 40 70 1 0 41 71 1 6 42 72 1 0 M END

Standard InCHIKey	ROKINGZIRKUMQG-GCRIMBLLSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-17(30)20(33)23(36)26(39-9)38-8-16-19(32)21(34)24(37)27(42-16)40-11-3-4-12-15(7-11)41-25(22(35)18(12)31)10-2-5-13(28)14(29)6-10/h2-7,9,16-17,19-21,23-24,26-30,32-37H,8H2,1H3/t9-,16-,17+,19-,20+,21+,23-,24-,26-,27-/m1/s1
SMILES	C[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC=C4C(=O)C(O)=C(C5=CC=C(O)C(O)=C5)OC4=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	-0.757 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.33 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.24 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.149	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.667	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0.615	Fluc inhibitor:	0.345 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.911 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.655 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.187	Promiscuous compounds:	0.487

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.571	MDCK Permeability:	-5.07
Pgp-inhibitor:	0.0	Pgp-substrate:	0.17
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.931
20% Bioavailability (F20%):	0.496	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.061
Plasma Protein Binding (PPB):	81.098%	Volume Distribution (VD):	-0.129
Fu:	17.418% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.392
BSEP inhibitor:	0.022

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:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.057
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.849 ? 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):

1.238

Half-life (T1/2):

5.357

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.346
Human Hepatotoxicity (H-HT):	0.261	Drug-induced Liver Injury (DILI):	0.928
AMES Toxicity:	0.712	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	0.898
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.422	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.958
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.405
Genotoxicity:	0.25	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.413	Hek293 Cytotoxicity:	0.13
BCF:	0.679 ? 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:	3.368 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.91 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.304 ? 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
NPO53145	Baptisia lecontei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63548	Baptisia simplicifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO55530	Baptisia sphaerocarpa	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 NPC571492 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	15385
0.1-0.2	30212
0.2-0.3	3359
0.3-0.4	539
0.4-0.5	276
0.5-0.6	67
0.6-0.7	17
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
0.7857	Intermediate Similarity	NPC67105
0.7045	Intermediate Similarity	NPC227508
0.6778	Remote Similarity	NPC210073
0.6556	Remote Similarity	NPC187379
0.6413	Remote Similarity	NPC203259
0.6413	Remote Similarity	NPC33054
0.6413	Remote Similarity	NPC176740
0.6413	Remote Similarity	NPC471725
0.6413	Remote Similarity	NPC134532
0.6413	Remote Similarity	NPC602582
0.6353	Remote Similarity	NPC238376
0.6277	Remote Similarity	NPC126784
0.6277	Remote Similarity	NPC241423
0.6211	Remote Similarity	NPC470443
0.6186	Remote Similarity	NPC473073
0.617	Remote Similarity	NPC186816
0.6129	Remote Similarity	NPC44931
0.6129	Remote Similarity	NPC275454
0.6064	Remote Similarity	NPC233994
0.5957	Remote Similarity	NPC173582
0.5957	Remote Similarity	NPC265885
0.5957	Remote Similarity	NPC181465
0.5957	Remote Similarity	NPC215710
0.5957	Remote Similarity	NPC473438
0.5957	Remote Similarity	NPC253788
0.5895	Remote Similarity	NPC22062
0.5895	Remote Similarity	NPC65563
0.5895	Remote Similarity	NPC473634
0.5895	Remote Similarity	NPC470949
0.5895	Remote Similarity	NPC138811
0.5876	Remote Similarity	NPC211532
0.5876	Remote Similarity	NPC488364
0.5833	Remote Similarity	NPC204693
0.5816	Remote Similarity	NPC209296
0.5789	Remote Similarity	NPC39834
0.5773	Remote Similarity	NPC475366
0.573	Remote Similarity	NPC168822
0.5686	Remote Similarity	NPC244875
0.567	Remote Similarity	NPC473571
0.567	Remote Similarity	NPC110941
0.5619	Remote Similarity	NPC480441
0.5618	Remote Similarity	NPC108831
0.5618	Remote Similarity	NPC182634
0.5588	Remote Similarity	NPC135358
0.5567	Remote Similarity	NPC156869
0.5556	Remote Similarity	NPC65711
0.5556	Remote Similarity	NPC277205
0.5556	Remote Similarity	NPC37919
0.5545	Remote Similarity	NPC476472
0.5545	Remote Similarity	NPC294815
0.5545	Remote Similarity	NPC16194
0.55	Remote Similarity	NPC473327
0.5474	Remote Similarity	NPC477848
0.5464	Remote Similarity	NPC67326
0.5455	Remote Similarity	NPC488073
0.5417	Remote Similarity	NPC254540
0.5408	Remote Similarity	NPC303913
0.5392	Remote Similarity	NPC89127
0.5347	Remote Similarity	NPC122467
0.534	Remote Similarity	NPC287889
0.5326	Remote Similarity	NPC271692
0.5312	Remote Similarity	NPC116864
0.5312	Remote Similarity	NPC244776
0.53	Remote Similarity	NPC488074
0.5288	Remote Similarity	NPC470446
0.5275	Remote Similarity	NPC19709
0.5269	Remote Similarity	NPC117260
0.5263	Remote Similarity	NPC99957
0.5253	Remote Similarity	NPC473512
0.5238	Remote Similarity	NPC603856
0.5234	Remote Similarity	NPC292019
0.5234	Remote Similarity	NPC202908
0.5217	Remote Similarity	NPC609879
0.5196	Remote Similarity	NPC51326
0.5192	Remote Similarity	NPC101636
0.5192	Remote Similarity	NPC470445
0.5185	Remote Similarity	NPC25523
0.5161	Remote Similarity	NPC245014
0.5158	Remote Similarity	NPC181616
0.5146	Remote Similarity	NPC142142
0.51	Remote Similarity	NPC129827
0.5096	Remote Similarity	NPC80068
0.5096	Remote Similarity	NPC231194
0.5051	Remote Similarity	NPC471079
0.5049	Remote Similarity	NPC229409
0.5048	Remote Similarity	NPC235575

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC571492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4377
0.1-0.2	4683
0.2-0.3	78
0.3-0.4	5
0.4-0.5	2
0.5-0.6	3
0.6-0.7	2
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
0.6413	Remote Similarity	NPD6797	Phase 2
0.6354	Remote Similarity	NPD7251	Phase 2
0.5816	Remote Similarity	NPD7054	Phase 4
0.5631	Remote Similarity	NPD7808	Phase 3
0.5481	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