NPASS Compound

Natural Product: NPC122894

Natural Product ID	NPC122894
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dichamanetin
IUPAC Name	(2S)-5,7-dihydroxy-6,8-bis[(2-hydroxyphenyl)methyl]-2-phenyl-2,3-dihydrochromen-4-one
Synonyms	Dichamanetin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1835968
PubChem CID	181193
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

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 59 63 0 0 0 0 0 0 0 0999 V2000 -6.7043 -2.7110 0.1876 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9972 -2.0516 1.1770 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6371 -1.8411 1.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9164 -2.2845 0.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6361 -2.9487 -0.9886 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9958 -3.1605 -0.9068 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4776 -2.0470 -0.0623 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6677 -2.9752 0.8115 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2340 -2.7592 0.4576 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5935 -3.6808 0.3586 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1771 -1.3715 0.2220 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5274 -1.0499 0.0481 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8882 0.2548 -0.1727 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2782 0.6811 -0.3773 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2803 -0.3920 -0.2445 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8071 -0.9756 -1.3936 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7417 -1.9848 -1.3673 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1801 -2.4429 -0.1333 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6615 -1.8678 1.0063 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7259 -0.8576 0.9713 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2502 -0.3267 2.1587 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9151 1.2533 -0.2228 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4136 0.9549 -0.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4926 1.9371 -0.0870 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1287 3.3225 -0.3140 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3070 3.8962 -1.5496 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9621 5.2292 -1.7912 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4384 5.9763 -0.7834 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2577 5.4066 0.4575 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5992 4.0926 0.6909 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3857 3.5789 1.9847 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7794 -0.3785 0.1697 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1246 -0.7110 0.3425 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2901 2.5513 -0.4444 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4485 -2.0650 0.1049 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7738 -2.8780 0.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5371 -1.6845 2.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0899 -1.3190 1.8777 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1128 -3.3144 -1.8577 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5640 -3.6754 -1.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1323 -2.2268 -1.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8898 -2.7265 1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0001 -4.0178 0.5528 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5609 1.5074 0.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4271 1.1624 -1.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4676 -0.6254 -2.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1267 -2.4142 -2.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9237 -3.2455 -0.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0224 -2.2424 1.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9430 0.0104 2.8242 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0591 1.8380 0.8921 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2490 1.5510 -0.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7167 3.3476 -2.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0995 5.6916 -2.7644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1682 7.0238 -0.9801 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1622 6.0126 1.2553 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4855 3.8748 2.4230 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0780 2.8437 -1.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5859 -2.7452 -0.6395 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 4 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 13 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 23 32 2 0 32 33 1 0 22 34 1 0 12 35 1 0 6 1 1 0 33 7 1 0 32 11 1 0 20 15 1 0 30 25 1 0 1 36 1 0 2 37 1 0 3 38 1 0 5 39 1 0 6 40 1 0 7 41 1 6 8 42 1 0 8 43 1 0 14 44 1 0 14 45 1 0 16 46 1 0 17 47 1 0 18 48 1 0 19 49 1 0 21 50 1 0 24 51 1 0 24 52 1 0 26 53 1 0 27 54 1 0 28 55 1 0 29 56 1 0 31 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	WBZSDBHJYZORRP-VWLOTQADSA-N
Standard InCHI	InChI=1S/C29H24O6/c30-22-12-6-4-10-18(22)14-20-27(33)21(15-19-11-5-7-13-23(19)31)29-26(28(20)34)24(32)16-25(35-29)17-8-2-1-3-9-17/h1-13,25,30-31,33-34H,14-16H2/t25-/m0/s1
SMILES	c1ccc(cc1)[C@@H]1CC(=O)c2c(c(Cc3ccccc3O)c(c(Cc3ccccc3O)c2O1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.16	Volume:	485.825 ? Van der Waals volume.
Dense:	0.964	LogP:	4.978 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.461 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.643 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	30.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.313	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.188	Fsp³:	0.138
MCE-18:	87.394 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.998	Fluc inhibitor:	0.277 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.428 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.684 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.319	Promiscuous compounds:	0.031

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.022	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.972	Pgp-substrate:	0.0
PAMPA:	0.967 ? 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):	0.091
20% Bioavailability (F20%):	0.068	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.992
Plasma Protein Binding (PPB):	97.696%	Volume Distribution (VD):	0.326
Fu:	1.993% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.06
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.86
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.798	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.906	CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.954
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.84
HLM stability:	0.931 ? 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):

4.859

Half-life (T1/2):

1.041

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.765
Human Hepatotoxicity (H-HT):	0.781	Drug-induced Liver Injury (DILI):	0.027
AMES Toxicity:	0.568	Rat Oral Acute Toxicity:	0.365
Maximum Recommended Daily Dose:	0.571	Skin Sensitization:	0.947
Carcinogencity:	0.117	Eye Corrosion:	0.005
Eye Irritation:	0.994	Respiratory Toxicity:	0.779
Drug-induced Neurotoxicity:	0.376	Ototoxicity:	0.152
Hematotoxicity:	0.051	Drug-induced Nephrotoxicity:	0.304
Genotoxicity:	0.868	RPMI-8226 Immunitoxicity:	0.193
A549 Cytotoxicity:	0.696	Hek293 Cytotoxicity:	0.773
BCF:	1.376 ? 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:	5.378 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.262 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.092 ? 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
NPO22391	Tripterygium forrestii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(92)80491-V]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662101]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO22825	Pleurocybella porrigens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057752]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	twig	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	aerial parts	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	stem	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21973101]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	Leaf; Twig	n.a.	n.a.	PMID[30835120]
NPO41040	Sphaerocoryne gracilis ssp. gracilis	Strain	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32067457]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22825	Pleurocybella porrigens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19112	Evolvulus nummularius	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22825	Pleurocybella porrigens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20818	Lactarius subumbonatus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19112	Evolvulus nummularius	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20366	Fontinalis antipyretica	Species	Fontinalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17204	Helminthosporium avenae	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22391	Tripterygium forrestii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17482	Menispermum dahuricum	Species	Menispermaceae	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	3
ED50	2
MIC	2
GI	1

Activity Type	# Activity
Individual protein	1
Cell line	3
Organism	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4381	Individual protein	Cell division protein ftsZ	Escherichia coli K-12	IC50	=	12500.0	nM	PMID[25791674]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell line	HT-29	Homo sapiens	ED50	>	20.0	uM	PMID[21973101]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	3.6	uM	PMID[21973101]
NPT71	Cell line	HEK293	Homo sapiens	GI	=	75.0	%	PMID[32067457]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9300.0	nM	PMID[32067457]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6700.0	nM	PMID[32067457]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5.01	ug.mL-1	PMID[25791674]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.8	ug.mL-1	PMID[25791674]

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 NPC122894 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	26367
0.1-0.2	21502
0.2-0.3	1598
0.3-0.4	294
0.4-0.5	64
0.5-0.6	19
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC78324
0.85	High Similarity	NPC115601
0.85	High Similarity	NPC39154
0.85	High Similarity	NPC208011
0.7895	Intermediate Similarity	NPC3642
0.7119	Intermediate Similarity	NPC39045
0.6557	Remote Similarity	NPC109183
0.6349	Remote Similarity	NPC470135
0.619	Remote Similarity	NPC26238
0.6176	Remote Similarity	NPC132345
0.6094	Remote Similarity	NPC470131
0.6094	Remote Similarity	NPC470132
0.5846	Remote Similarity	NPC470133
0.5593	Remote Similarity	NPC248372
0.5479	Remote Similarity	NPC228779
0.5479	Remote Similarity	NPC483811
0.5424	Remote Similarity	NPC213322
0.541	Remote Similarity	NPC215885
0.541	Remote Similarity	NPC110776
0.541	Remote Similarity	NPC110038
0.5333	Remote Similarity	NPC482121
0.5333	Remote Similarity	NPC270964
0.5238	Remote Similarity	NPC2416
0.5238	Remote Similarity	NPC271590
0.5224	Remote Similarity	NPC243528
0.5161	Remote Similarity	NPC194432
0.5082	Remote Similarity	NPC243083
0.5082	Remote Similarity	NPC13768
0.5082	Remote Similarity	NPC287246
0.5079	Remote Similarity	NPC324134
0.5079	Remote Similarity	NPC40833

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC122894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4305
0.1-0.2	4757
0.2-0.3	82
0.3-0.4	2
0.4-0.5	3
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
0.5082	Remote Similarity	NPD1550	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