NPASS Compound

Natural Product: NPC241423

Natural Product ID	NPC241423
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Patuletin 3-O-Beta-D-Robinobioside
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL442920
PubChem CID	44575854
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 6.1304 0.9212 4.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5350 2.1019 3.3447 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5608 2.7428 2.3972 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9331 4.0889 2.0853 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4442 4.0571 2.1992 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8190 2.7058 1.8906 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5668 2.5723 2.2300 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4091 2.3382 1.7402 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0695 1.0906 0.9841 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6230 1.1660 -0.4453 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4628 -0.2040 -1.0373 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2682 -0.8996 -0.4836 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7668 -0.0596 0.1499 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3358 1.0739 0.7851 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9362 0.2384 -0.6325 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9798 -0.6822 -0.7426 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8392 -0.8348 0.3233 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6675 -0.1366 1.3655 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8641 -1.7473 0.2246 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9903 -2.4835 -0.9561 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0131 -3.4096 -1.0779 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8900 -3.6039 -0.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7373 -2.8637 1.0944 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7391 -1.9344 1.2611 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5874 -1.1947 2.4102 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6554 -3.1013 2.1064 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4330 -4.1163 3.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9044 -4.5372 -0.2119 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1566 -2.2895 -1.9118 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1371 -1.4142 -1.8802 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3216 -1.3439 -3.0801 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4180 -2.3340 -4.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7302 -2.2584 -5.2455 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9158 -1.1623 -5.5143 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8179 -0.1849 -4.5720 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5247 -0.2874 -3.3604 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0100 0.9149 -4.8323 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2503 -1.1468 -6.7458 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6885 -1.8621 0.5063 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5707 -0.2052 -2.4182 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9272 2.1307 -1.1800 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5382 1.6651 2.5152 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9253 4.9633 1.2695 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4208 4.6026 0.8916 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8024 2.8484 2.9937 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0112 0.0289 3.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1920 1.0876 4.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4617 0.7254 4.9522 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2212 2.9123 4.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6171 2.1823 1.4503 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3084 4.7683 2.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0783 4.3647 3.1960 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0242 2.5503 0.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6308 2.3540 2.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9573 3.1776 1.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4133 0.1704 1.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6678 1.4058 -0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3765 -0.7860 -0.6896 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1582 -1.5441 -1.2631 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2222 -0.7369 0.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0634 -3.9605 -2.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1074 -1.5246 3.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8181 -5.1170 2.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9579 -3.7962 4.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3501 -4.2263 3.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6936 -5.3503 -0.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0394 -3.1843 -3.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -3.0210 -5.9830 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3700 0.5606 -2.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9966 0.8932 -4.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7537 -1.0221 -6.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1146 -2.3097 0.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4247 0.2322 -2.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4583 2.3169 -1.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1307 4.6050 0.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4177 3.9174 0.1627 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4882 2.4018 2.4378 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 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 23 26 1 0 26 27 1 0 22 28 1 0 20 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 34 38 1 0 12 39 1 0 11 40 1 0 10 41 1 0 6 42 1 0 5 43 1 0 4 44 1 0 3 45 1 0 42 2 1 0 14 9 1 0 30 16 2 0 36 31 1 0 24 19 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 1 3 50 1 6 4 51 1 1 5 52 1 1 6 53 1 6 8 54 1 0 8 55 1 0 9 56 1 1 10 57 1 1 11 58 1 1 12 59 1 6 13 60 1 1 21 61 1 0 25 62 1 0 27 63 1 0 27 64 1 0 27 65 1 0 28 66 1 0 32 67 1 0 33 68 1 0 36 69 1 0 37 70 1 0 38 71 1 0 39 72 1 0 40 73 1 0 41 74 1 0 43 75 1 0 44 76 1 0 45 77 1 0 M END

Standard InCHIKey	MLOJYABWNDVJMG-GBWWRXBVSA-N
Standard InCHI	InChI=1S/C28H32O17/c1-8-16(32)20(36)22(38)27(42-8)41-7-14-17(33)21(37)23(39)28(44-14)45-26-19(35)15-13(6-12(31)25(40-2)18(15)34)43-24(26)9-3-4-10(29)11(30)5-9/h3-6,8,14,16-17,20-23,27-34,36-39H,7H2,1-2H3/t8-,14+,16-,17-,20+,21-,22+,23+,27+,28-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(c(c3O)OC)O)oc2c2ccc(c(c2)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	640.16	Volume:	578.404 ? Van der Waals volume.
Dense:	1.107	LogP:	0.391 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.828 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.164 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	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:	0.129	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.88	Fsp³:	0.464
MCE-18:	125.561 ? 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:	0.61	Fluc inhibitor:	0.27 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.822 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.611 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.092	Promiscuous compounds:	0.662

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.366	MDCK Permeability:	-5.287
Pgp-inhibitor:	0.0	Pgp-substrate:	0.842
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):	0.51
20% Bioavailability (F20%):	0.882	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.552
Plasma Protein Binding (PPB):	81.946%	Volume Distribution (VD):	-0.04
Fu:	16.498% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.127
BSEP inhibitor:	0.0

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:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.038
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.99
HLM stability:	0.814 ? 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):

1.652

Half-life (T1/2):

3.617

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.262
Human Hepatotoxicity (H-HT):	0.362	Drug-induced Liver Injury (DILI):	0.824
AMES Toxicity:	0.885	Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.043	Skin Sensitization:	1.0
Carcinogencity:	0.034	Eye Corrosion:	0.0
Eye Irritation:	0.36	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.955
Hematotoxicity:	0.093	Drug-induced Nephrotoxicity:	0.189
Genotoxicity:	0.694	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.916	Hek293 Cytotoxicity:	0.473
BCF:	0.424 ? 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:	3.014 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.534 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.739 ? 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
NPO8463	Brickellia arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6429283]
NPO8463	Brickellia arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8463	Brickellia arguta	Species	Asteraceae	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

Activity Type	# Activity
Inhibition	3

Activity Type	# Activity
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	Inhibition	=	86.0	%	PMID[18178085]
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	Inhibition	=	33.0	%	PMID[18178085]
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	Inhibition	=	11.0	%	PMID[18178085]

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 NPC241423 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	18634
0.1-0.2	27371
0.2-0.3	2903
0.3-0.4	487
0.4-0.5	240
0.5-0.6	122
0.6-0.7	41
0.7-0.8	1
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126784
0.8902	High Similarity	NPC473571
0.8902	High Similarity	NPC110941
0.8795	High Similarity	NPC488073
0.8571	High Similarity	NPC488074
0.8228	Intermediate Similarity	NPC305811
0.8202	Intermediate Similarity	NPC470446
0.8118	Intermediate Similarity	NPC203259
0.8118	Intermediate Similarity	NPC33054
0.8118	Intermediate Similarity	NPC176740
0.8118	Intermediate Similarity	NPC471725
0.8118	Intermediate Similarity	NPC134532
0.8118	Intermediate Similarity	NPC602582
0.809	Intermediate Similarity	NPC470445
0.7841	Intermediate Similarity	NPC470443
0.7582	Intermediate Similarity	NPC473073
0.7391	Intermediate Similarity	NPC476472
0.7391	Intermediate Similarity	NPC294815
0.7391	Intermediate Similarity	NPC16194
0.7386	Intermediate Similarity	NPC173582
0.7386	Intermediate Similarity	NPC265885
0.7386	Intermediate Similarity	NPC181465
0.7386	Intermediate Similarity	NPC215710
0.7386	Intermediate Similarity	NPC473438
0.7386	Intermediate Similarity	NPC253788
0.7368	Intermediate Similarity	NPC470451
0.7363	Intermediate Similarity	NPC473327
0.7312	Intermediate Similarity	NPC470449
0.7303	Intermediate Similarity	NPC65563
0.7303	Intermediate Similarity	NPC470949
0.7262	Intermediate Similarity	NPC42773
0.7262	Intermediate Similarity	NPC45522
0.7204	Intermediate Similarity	NPC470447
0.7191	Intermediate Similarity	NPC39834
0.7111	Intermediate Similarity	NPC156869
0.7	Intermediate Similarity	NPC67326
0.6848	Remote Similarity	NPC186816
0.6804	Remote Similarity	NPC470455
0.6744	Remote Similarity	NPC27640
0.6667	Remote Similarity	NPC116864
0.6667	Remote Similarity	NPC244776
0.6632	Remote Similarity	NPC122467
0.66	Remote Similarity	NPC292019
0.66	Remote Similarity	NPC202908
0.6552	Remote Similarity	NPC271692
0.6512	Remote Similarity	NPC127546
0.6512	Remote Similarity	NPC57625
0.6512	Remote Similarity	NPC173637
0.6512	Remote Similarity	NPC317489
0.6512	Remote Similarity	NPC223424
0.6512	Remote Similarity	NPC600591
0.6495	Remote Similarity	NPC89127
0.6452	Remote Similarity	NPC67105
0.6429	Remote Similarity	NPC36138
0.6364	Remote Similarity	NPC470450
0.6364	Remote Similarity	NPC488080
0.6364	Remote Similarity	NPC169977
0.6344	Remote Similarity	NPC471079
0.6214	Remote Similarity	NPC480441
0.6211	Remote Similarity	NPC210073
0.6176	Remote Similarity	NPC470416
0.6154	Remote Similarity	NPC101026
0.6154	Remote Similarity	NPC488077
0.6146	Remote Similarity	NPC470444
0.6111	Remote Similarity	NPC59534
0.6082	Remote Similarity	NPC153755
0.6078	Remote Similarity	NPC89052
0.6058	Remote Similarity	NPC303694
0.6055	Remote Similarity	NPC241781
0.6042	Remote Similarity	NPC605592
0.602	Remote Similarity	NPC12013
0.602	Remote Similarity	NPC483414
0.602	Remote Similarity	NPC11432
0.602	Remote Similarity	NPC483415
0.602	Remote Similarity	NPC477613
0.6019	Remote Similarity	NPC189564
0.6	Remote Similarity	NPC471669
0.5962	Remote Similarity	NPC173837
0.596	Remote Similarity	NPC483416
0.5922	Remote Similarity	NPC203145
0.5914	Remote Similarity	NPC223747
0.59	Remote Similarity	NPC142142
0.5889	Remote Similarity	NPC265530
0.5882	Remote Similarity	NPC223426
0.5872	Remote Similarity	NPC156785
0.5872	Remote Similarity	NPC162394
0.587	Remote Similarity	NPC175107
0.587	Remote Similarity	NPC219904
0.587	Remote Similarity	NPC488071
0.5843	Remote Similarity	NPC111929
0.5843	Remote Similarity	NPC320283
0.5843	Remote Similarity	NPC41121
0.5825	Remote Similarity	NPC81042
0.5824	Remote Similarity	NPC46420
0.58	Remote Similarity	NPC37668
0.5789	Remote Similarity	NPC95866
0.5789	Remote Similarity	NPC265115
0.5784	Remote Similarity	NPC221342
0.5784	Remote Similarity	NPC476470
0.5773	Remote Similarity	NPC227508
0.5745	Remote Similarity	NPC605784
0.5743	Remote Similarity	NPC486577
0.5728	Remote Similarity	NPC602448
0.5714	Remote Similarity	NPC145038
0.5714	Remote Similarity	NPC56077
0.5714	Remote Similarity	NPC281131
0.5714	Remote Similarity	NPC253662
0.5714	Remote Similarity	NPC179950
0.5714	Remote Similarity	NPC158674
0.5714	Remote Similarity	NPC88789
0.5714	Remote Similarity	NPC488075
0.5714	Remote Similarity	NPC491374
0.57	Remote Similarity	NPC480471
0.57	Remote Similarity	NPC488076
0.5696	Remote Similarity	NPC163524
0.567	Remote Similarity	NPC187379
0.567	Remote Similarity	NPC609888
0.5667	Remote Similarity	NPC135599
0.5667	Remote Similarity	NPC73855
0.5667	Remote Similarity	NPC113968
0.5667	Remote Similarity	NPC328940
0.5667	Remote Similarity	NPC277174
0.5667	Remote Similarity	NPC606877
0.5657	Remote Similarity	NPC204693
0.5644	Remote Similarity	NPC209296
0.5612	Remote Similarity	NPC44931
0.5607	Remote Similarity	NPC25523
0.5591	Remote Similarity	NPC599850
0.5588	Remote Similarity	NPC64755
0.5575	Remote Similarity	NPC192539
0.5556	Remote Similarity	NPC22062
0.5556	Remote Similarity	NPC473634
0.5556	Remote Similarity	NPC155877
0.5556	Remote Similarity	NPC138811
0.5536	Remote Similarity	NPC488078
0.5532	Remote Similarity	NPC611303
0.5524	Remote Similarity	NPC14187
0.551	Remote Similarity	NPC480466
0.5455	Remote Similarity	NPC471748
0.5444	Remote Similarity	NPC276222
0.5444	Remote Similarity	NPC274618
0.5444	Remote Similarity	NPC118284
0.5444	Remote Similarity	NPC608147
0.5435	Remote Similarity	NPC249281
0.5417	Remote Similarity	NPC99957
0.541	Remote Similarity	NPC487500
0.5408	Remote Similarity	NPC254540
0.54	Remote Similarity	NPC233994
0.5398	Remote Similarity	NPC480444
0.5385	Remote Similarity	NPC67037
0.5385	Remote Similarity	NPC85751
0.5385	Remote Similarity	NPC255615
0.5385	Remote Similarity	NPC19240
0.5385	Remote Similarity	NPC487499
0.5377	Remote Similarity	NPC214621
0.5377	Remote Similarity	NPC34267
0.5376	Remote Similarity	NPC136042
0.5366	Remote Similarity	NPC487501
0.5364	Remote Similarity	NPC139571
0.5361	Remote Similarity	NPC276377
0.536	Remote Similarity	NPC482521
0.5354	Remote Similarity	NPC29958
0.5347	Remote Similarity	NPC129264
0.534	Remote Similarity	NPC270448
0.5339	Remote Similarity	NPC275977
0.5339	Remote Similarity	NPC473554
0.5333	Remote Similarity	NPC487502
0.5327	Remote Similarity	NPC121703
0.5321	Remote Similarity	NPC217520
0.5319	Remote Similarity	NPC84362
0.5319	Remote Similarity	NPC349108
0.531	Remote Similarity	NPC474522
0.5294	Remote Similarity	NPC470125
0.5294	Remote Similarity	NPC154741
0.525	Remote Similarity	NPC72554
0.5243	Remote Similarity	NPC211532
0.5243	Remote Similarity	NPC488364
0.5238	Remote Similarity	NPC482520
0.5238	Remote Similarity	NPC473071
0.5238	Remote Similarity	NPC483412
0.5238	Remote Similarity	NPC482519
0.5229	Remote Similarity	NPC477895
0.5204	Remote Similarity	NPC203050
0.5204	Remote Similarity	NPC225434
0.5204	Remote Similarity	NPC476215
0.5175	Remote Similarity	NPC488740
0.5175	Remote Similarity	NPC488736
0.5175	Remote Similarity	NPC488733
0.5158	Remote Similarity	NPC24043
0.5158	Remote Similarity	NPC52550
0.5155	Remote Similarity	NPC120099
0.5146	Remote Similarity	NPC475366
0.5128	Remote Similarity	NPC480442
0.5106	Remote Similarity	NPC77672
0.5106	Remote Similarity	NPC133671
0.5106	Remote Similarity	NPC135391
0.5106	Remote Similarity	NPC78263
0.5106	Remote Similarity	NPC250069
0.5106	Remote Similarity	NPC238376

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC241423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5197
0.1-0.2	3901
0.2-0.3	42
0.3-0.4	4
0.4-0.5	1
0.5-0.6	3
0.6-0.7	0
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
0.8118	Intermediate Similarity	NPD6797	Phase 2
0.7204	Intermediate Similarity	NPD7251	Phase 2
0.5922	Remote Similarity	NPD7808	Phase 3
0.5644	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