NPASS Compound

Natural Product: NPC72425

Natural Product ID	NPC72425
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Robustaflavone-4'-Methyl Ether
IUPAC Name	6-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms	Robustaflavone-4'-Methyl Ether
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451902
PubChem CID	11757331
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 61 66 0 0 0 0 0 0 0 0999 V2000 1.7994 4.4415 0.0618 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2912 3.1527 0.0385 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0116 2.7736 0.1692 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0297 3.6640 0.3229 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3030 3.1543 0.4437 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6055 1.8104 0.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5459 0.9573 0.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2462 1.3794 0.1372 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 0.4915 -0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5658 0.0510 1.1449 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0584 0.4761 2.3678 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6657 -0.7576 1.1200 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1827 -1.1864 -0.1168 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -0.7655 -1.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4351 0.0480 -1.1855 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8255 0.4445 -2.3725 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0405 -1.1764 -2.4751 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4813 -0.8123 -3.5262 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1703 -1.9970 -2.4672 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7767 -2.3900 -1.2958 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2267 -1.9478 -0.1671 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9552 -3.2366 -1.2263 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4673 -3.5698 0.0010 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6086 -4.3589 0.1128 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2540 -4.8281 -1.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7405 -4.4939 -2.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5954 -3.7004 -2.3419 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3957 -5.6146 -0.8662 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9985 1.3477 0.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3350 0.0212 0.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6689 -0.3730 0.6221 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9990 -1.5955 0.5891 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6370 0.5917 0.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2422 1.9121 0.8121 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9734 2.2175 0.6936 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2245 2.8726 0.9702 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5673 2.5322 1.0951 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9615 1.1981 1.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9769 0.2582 0.9044 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3031 -1.0968 0.8632 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5664 3.4745 1.2546 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4849 4.5637 -0.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0487 5.2495 -0.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3852 4.6202 1.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8475 4.7300 0.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1073 3.8556 0.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7263 -0.1191 0.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6766 0.9962 2.9860 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1745 -1.0906 2.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1539 -0.1217 -2.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5604 -2.3137 -3.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9710 -3.2082 0.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0268 -4.6339 1.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2255 -4.8457 -3.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2212 -3.4609 -3.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1480 -5.3816 -0.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5802 -0.7467 0.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9340 3.9193 0.9957 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9784 0.8704 1.1529 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2496 -1.4337 0.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4596 3.1815 1.6082 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 2 0 8 9 1 0 9 10 2 0 10 11 1 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 14 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 25 28 1 0 6 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 37 41 1 0 8 3 1 0 15 9 1 0 27 22 1 0 35 29 1 0 21 13 1 0 39 33 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 5 46 1 0 7 47 1 0 11 48 1 0 12 49 1 0 16 50 1 0 19 51 1 0 23 52 1 0 24 53 1 0 26 54 1 0 27 55 1 0 28 56 1 0 30 57 1 0 36 58 1 0 38 59 1 0 40 60 1 0 41 61 1 0 M END

Standard InCHIKey	ZBOKFHZIWKIWRZ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C31H20O10/c1-39-23-7-4-15(25-11-21(36)29-19(34)9-17(33)10-26(29)41-25)8-18(23)28-20(35)13-27-30(31(28)38)22(37)12-24(40-27)14-2-5-16(32)6-3-14/h2-13,32-35,38H,1H3
SMILES	COc1ccc(cc1c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O)c1cc(=O)c2c(o1)cc(cc2O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.11	Volume:	539.112 ? Van der Waals volume.
Dense:	1.024	LogP:	4.487 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.562 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.423 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	36.0
TPSA:	170.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.19	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.007	Fsp³:	0.032
MCE-18:	36.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.997	Fluc inhibitor:	0.685 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.918 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.993 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.533	Promiscuous compounds:	0.893

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.125	MDCK Permeability:	-4.806
Pgp-inhibitor:	0.001	Pgp-substrate:	0.676
PAMPA:	0.919 ? 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):	0.001
20% Bioavailability (F20%):	0.632	30% Bioavailability (F30%):	0.922
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.944
Plasma Protein Binding (PPB):	96.803%	Volume Distribution (VD):	-0.358
Fu:	2.058% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.805
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.73
BSEP inhibitor:	0.935

ADMET: Metabolism

CYP1A2-inhibitor:	0.091	CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.278	CYP2C9-substrate:	0.707
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.901 ? 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):

1.469

Half-life (T1/2):

1.859

ADMET: Toxicity

hERG Blockers:	0.109	hERG Blockers (10um):	0.528
Human Hepatotoxicity (H-HT):	0.449	Drug-induced Liver Injury (DILI):	0.961
AMES Toxicity:	0.694	Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	0.502
Carcinogencity:	0.826	Eye Corrosion:	0.001
Eye Irritation:	0.995	Respiratory Toxicity:	0.877
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.047
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.008
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.095
A549 Cytotoxicity:	0.809	Hek293 Cytotoxicity:	0.985
BCF:	1.137 ? 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:	4.481 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.959 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.751 ? 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
NPO2508	Selaginella delicatula	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843573]
NPO2508	Selaginella delicatula	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27231	Herba selaginellae doederleinii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2508	Selaginella delicatula	Species	Selaginellaceae	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
IC50	7
Inhibition	12

Activity Type	# Activity
Individual protein	3
Cell line	16

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT280	Individual protein	Matrix metalloproteinase 9	Homo sapiens	IC50	=	26080.0	nM	PMID[29921475]
NPT567	Individual protein	Matrix metalloproteinase 3	Homo sapiens	IC50	=	37280.0	nM	PMID[29921475]
NPT568	Individual protein	Matrix metalloproteinase-2	Homo sapiens	IC50	>	100000.0	nM	PMID[29921475]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell line	Raji	Homo sapiens	Inhibition	=	98.4	%	PMID[10843573]
NPT80	Cell line	Raji	Homo sapiens	Inhibition	=	68.5	%	PMID[10843573]
NPT80	Cell line	Raji	Homo sapiens	Inhibition	=	60.7	%	PMID[10843573]
NPT80	Cell line	Raji	Homo sapiens	Inhibition	=	34.2	%	PMID[10843573]
NPT1307	Cell line	Calu-1	Homo sapiens	Inhibition	=	100.0	%	PMID[10843573]
NPT1307	Cell line	Calu-1	Homo sapiens	Inhibition	=	77.9	%	PMID[10843573]
NPT1307	Cell line	Calu-1	Homo sapiens	Inhibition	=	44.6	%	PMID[10843573]
NPT1307	Cell line	Calu-1	Homo sapiens	Inhibition	=	42.6	%	PMID[10843573]
NPT111	Cell line	K562	Homo sapiens	Inhibition	=	10.8	%	PMID[10843573]
NPT189	Cell line	Vero	Chlorocebus aethiops	Inhibition	=	6.6	%	PMID[10843573]
NPT1306	Cell line	WISH	Homo sapiens	Inhibition	=	-90.0	%	PMID[10843573]
NPT165	Cell line	HeLa	Homo sapiens	Inhibition	=	5.5	%	PMID[10843573]
NPT3140	Cell line	MGC-803	Homo sapiens	IC50	=	21780.0	nM	PMID[29921475]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	26570.0	nM	PMID[29921475]
NPT81	Cell line	A549	Homo sapiens	IC50	=	25640.0	nM	PMID[29921475]
NPT550	Cell line	T-24	Homo sapiens	IC50	=	25790.0	nM	PMID[29921475]

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 NPC72425 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	30482
0.1-0.2	16620
0.2-0.3	1780
0.3-0.4	754
0.4-0.5	161
0.5-0.6	34
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8143	Intermediate Similarity	NPC205026
0.7714	Intermediate Similarity	NPC71061
0.7313	Intermediate Similarity	NPC111112
0.726	Intermediate Similarity	NPC215203
0.7083	Intermediate Similarity	NPC150908
0.6875	Remote Similarity	NPC231772
0.6849	Remote Similarity	NPC600972
0.6667	Remote Similarity	NPC186227
0.6533	Remote Similarity	NPC303485
0.6452	Remote Similarity	NPC50898
0.641	Remote Similarity	NPC265624
0.6316	Remote Similarity	NPC290830
0.6282	Remote Similarity	NPC601565
0.6143	Remote Similarity	NPC67322
0.6087	Remote Similarity	NPC52005
0.6087	Remote Similarity	NPC12200
0.6026	Remote Similarity	NPC272064
0.6	Remote Similarity	NPC183950
0.6	Remote Similarity	NPC603692
0.589	Remote Similarity	NPC138299
0.5823	Remote Similarity	NPC159707
0.5823	Remote Similarity	NPC14606
0.5658	Remote Similarity	NPC34089
0.5658	Remote Similarity	NPC183
0.5658	Remote Similarity	NPC196179
0.5652	Remote Similarity	NPC62536
0.5652	Remote Similarity	NPC120464
0.5652	Remote Similarity	NPC483773
0.5652	Remote Similarity	NPC601901
0.56	Remote Similarity	NPC291746
0.5522	Remote Similarity	NPC279121
0.5513	Remote Similarity	NPC259757
0.5507	Remote Similarity	NPC241498
0.5455	Remote Similarity	NPC78540
0.5432	Remote Similarity	NPC194593
0.5429	Remote Similarity	NPC234133
0.5417	Remote Similarity	NPC606638
0.5405	Remote Similarity	NPC605634
0.5395	Remote Similarity	NPC112954
0.5375	Remote Similarity	NPC601984
0.5366	Remote Similarity	NPC121649
0.5294	Remote Similarity	NPC274121
0.5286	Remote Similarity	NPC301323
0.5286	Remote Similarity	NPC103342
0.5256	Remote Similarity	NPC254351
0.525	Remote Similarity	NPC248739
0.5211	Remote Similarity	NPC241838
0.5139	Remote Similarity	NPC600900
0.5135	Remote Similarity	NPC610914
0.507	Remote Similarity	NPC156222
0.507	Remote Similarity	NPC47815
0.507	Remote Similarity	NPC29353
0.5054	Remote Similarity	NPC485523

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC72425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6045
0.1-0.2	3047
0.2-0.3	51
0.3-0.4	4
0.4-0.5	2
0.5-0.6	1
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
0.5522	Remote Similarity	NPD1511	Phase 2

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