NPASS Compound

Natural Product: NPC490336

Natural Product ID	NPC490336
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Luteolin 7-O-diglucuronide
IUPAC Name	n.a.
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:0002934] Flavonoid O-glucuronides [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

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 71 75 0 0 0 0 0 0 0 0999 V2000 -7.6679 2.1016 1.8735 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2139 1.7773 0.5972 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9177 0.9688 0.6823 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2724 -0.2456 1.2868 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4798 0.6809 -0.7072 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2102 0.0638 -0.7893 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9760 -1.1867 -1.2694 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9460 -1.8668 -1.6782 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6289 -1.8361 -1.3537 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6390 -1.0185 -0.8827 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7013 -1.7124 -0.1053 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4171 -0.9812 0.1927 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -1.3001 -0.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0603 -2.4089 -0.8860 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3581 -2.6945 -1.2288 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6395 -3.8282 -1.9510 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3771 -1.8623 -0.8587 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7033 -2.1209 -1.1892 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9873 -3.1516 -1.8497 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6786 -1.2263 -0.7757 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2582 -0.1258 -0.0549 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9893 0.0628 0.2254 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0292 -0.7365 -0.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7425 -0.4447 0.2127 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2102 0.8591 0.4162 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7585 1.9407 1.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6114 2.9147 1.6104 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9684 2.8117 1.3682 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8591 3.7887 1.8430 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4329 1.7404 0.6565 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7904 1.6366 0.4139 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5474 0.7649 0.1818 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4753 -2.1453 1.1358 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6602 -2.4640 2.1940 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3602 -3.2879 0.6890 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4922 -3.3601 1.4904 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7020 -3.2032 -0.7745 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9925 -4.1524 -1.5416 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4978 1.7215 -1.5886 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8221 2.9539 -1.1275 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0302 3.0129 -0.2415 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1667 3.2999 -0.9956 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6195 3.5837 -0.5189 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6413 4.8539 0.0400 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5168 2.9724 -0.4895 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6241 1.9612 1.9506 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0060 1.1690 0.1146 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2287 1.5575 1.2872 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1594 -0.5161 0.9443 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1998 -0.0912 -1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4337 -1.9654 -2.4603 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4597 -2.6147 -0.6883 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3154 -3.1183 -1.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9819 -3.7653 -2.8814 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7119 -1.4184 -1.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4728 0.4425 0.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6887 2.0522 1.3413 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2224 3.7523 2.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1559 4.5077 1.2097 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2006 2.2425 -0.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9834 -0.0588 -0.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1320 -1.3089 1.4179 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2518 -2.1123 2.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7829 -4.2227 0.8579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9744 -2.4964 1.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7765 -3.5473 -0.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5247 -4.3468 -2.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0625 3.5934 -2.0282 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8870 3.8735 0.4519 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0774 4.2399 -1.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1395 5.0405 0.9152 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 15 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 2 0 21 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 2 0 11 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 5 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 43 44 1 0 43 45 2 0 41 2 1 0 37 9 1 0 24 13 1 0 32 25 1 0 23 17 1 0 1 46 1 0 2 47 1 6 3 48 1 1 4 49 1 0 5 50 1 6 9 51 1 6 11 52 1 6 14 53 1 0 16 54 1 0 20 55 1 0 24 56 1 0 26 57 1 0 27 58 1 0 29 59 1 0 31 60 1 0 32 61 1 0 33 62 1 1 34 63 1 0 35 64 1 6 36 65 1 0 37 66 1 1 38 67 1 0 40 68 1 6 41 69 1 1 42 70 1 0 44 71 1 0 M END

Standard InCHIKey	SPWLSDULYCMRFB-VMEISIRMSA-N
Standard InCHI	InChI=1S/C27H26O18/c28-9-2-1-7(3-10(9)29)13-6-12(31)15-11(30)4-8(5-14(15)42-13)41-26-20(36)17(33)19(35)23(44-26)25(40)45-27-21(37)16(32)18(34)22(43-27)24(38)39/h1-6,16-23,26-30,32-37H,(H,38,39)/t16-,17-,18-,19-,20+,21+,22-,23-,26+,27-/m0/s1
SMILES	O[C@@H]1[C@@H](O)[C@H](OC(=O)[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(O)C(O)=C3)[C@H](O)[C@@H](O)[C@@H]2O)O[C@@H]([C@H]1O)C(O)=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.11	Volume:	564.625 ? Van der Waals volume.
Dense:	1.13	LogP:	-0.65 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.483 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.807 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	32.0
TPSA:	303.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.096	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.881	Fsp³:	0.37
MCE-18:	127.459 ? 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:	0.507	Fluc inhibitor:	0.359 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.979 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.764 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.383	Promiscuous compounds:	0.505

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.785	MDCK Permeability:	-5.073
Pgp-inhibitor:	0.0	Pgp-substrate:	0.616
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):	0.955
20% Bioavailability (F20%):	0.972	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.693
Plasma Protein Binding (PPB):	80.532%	Volume Distribution (VD):	-0.024
Fu:	16.471% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.478
OATP1B3 inhibitor:	0.95	BCRP inhibitor:	0.016
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.966
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.874
HLM stability:	0.006 ? 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):

0.791

Half-life (T1/2):

5.118

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.275	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.819	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.019	Skin Sensitization:	0.998
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.277	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.894
Hematotoxicity:	0.03	Drug-induced Nephrotoxicity:	0.645
Genotoxicity:	0.861	RPMI-8226 Immunitoxicity:	0.133
A549 Cytotoxicity:	0.522	Hek293 Cytotoxicity:	0.114
BCF:	0.325 ? 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:	2.957 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.487 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.696 ? 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
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO20640	Aloysia triphylla	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2838	Verbena officinalis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20640	Aloysia triphylla	Species	Verbenaceae	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
NPO20640	Aloysia triphylla	Other	n.a.	10.60000038	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO2838	Verbena officinalis	Raw	n.a.	495	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO2838	Verbena officinalis	n.a.	n.a.	495	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

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 NPC490336 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	21546
0.1-0.2	25452
0.2-0.3	2108
0.3-0.4	512
0.4-0.5	175
0.5-0.6	50
0.6-0.7	10
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
0.7674	Intermediate Similarity	NPC20505
0.7222	Intermediate Similarity	NPC190003
0.7143	Intermediate Similarity	NPC253685
0.6907	Remote Similarity	NPC229409
0.6889	Remote Similarity	NPC282169
0.663	Remote Similarity	NPC608742
0.6629	Remote Similarity	NPC19709
0.6593	Remote Similarity	NPC27942
0.6556	Remote Similarity	NPC189142
0.6556	Remote Similarity	NPC77660
0.6327	Remote Similarity	NPC210073
0.6304	Remote Similarity	NPC181712
0.62	Remote Similarity	NPC64051
0.598	Remote Similarity	NPC65711
0.5882	Remote Similarity	NPC46202
0.5859	Remote Similarity	NPC8856
0.5806	Remote Similarity	NPC473043
0.5806	Remote Similarity	NPC331652
0.5745	Remote Similarity	NPC39360
0.5745	Remote Similarity	NPC29763
0.5745	Remote Similarity	NPC210003
0.57	Remote Similarity	NPC606546
0.567	Remote Similarity	NPC135277
0.5631	Remote Similarity	NPC115674
0.5612	Remote Similarity	NPC22832
0.5612	Remote Similarity	NPC601144
0.5588	Remote Similarity	NPC44931
0.5521	Remote Similarity	NPC95090
0.5521	Remote Similarity	NPC27408
0.5472	Remote Similarity	NPC209296
0.5455	Remote Similarity	NPC243930
0.5455	Remote Similarity	NPC43211
0.5446	Remote Similarity	NPC600989
0.5421	Remote Similarity	NPC270675
0.5421	Remote Similarity	NPC195685
0.5417	Remote Similarity	NPC261866
0.5417	Remote Similarity	NPC238376
0.5413	Remote Similarity	NPC484301
0.54	Remote Similarity	NPC311830
0.5385	Remote Similarity	NPC22062
0.5385	Remote Similarity	NPC473634
0.5385	Remote Similarity	NPC138811
0.5361	Remote Similarity	NPC277205
0.5361	Remote Similarity	NPC37919
0.5288	Remote Similarity	NPC67105
0.5273	Remote Similarity	NPC472994
0.5243	Remote Similarity	NPC254540
0.5204	Remote Similarity	NPC168822
0.5204	Remote Similarity	NPC136042
0.52	Remote Similarity	NPC237435
0.5182	Remote Similarity	NPC101636
0.5152	Remote Similarity	NPC58716
0.5152	Remote Similarity	NPC84362
0.5152	Remote Similarity	NPC45638
0.5146	Remote Similarity	NPC4390
0.51	Remote Similarity	NPC201292
0.5098	Remote Similarity	NPC607707
0.5089	Remote Similarity	NPC14187
0.5088	Remote Similarity	NPC472993
0.5057	Remote Similarity	NPC108406
0.505	Remote Similarity	NPC210094
0.5046	Remote Similarity	NPC473623
0.5045	Remote Similarity	NPC298171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC490336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4489
0.1-0.2	4592
0.2-0.3	59
0.3-0.4	4
0.4-0.5	4
0.5-0.6	2
0.6-0.7	0
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
0.5472	Remote Similarity	NPD7054	Phase 4
0.52	Remote Similarity	NPD4338	Clinical (unspecified phase)

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