NPASS Compound

Natural Product: NPC217677

Natural Product ID	NPC217677
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cratoxyarborenone C
IUPAC Name	1,3-dihydroxy-5,7-dimethoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms	cratoxyarborenone C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL459105
PubChem CID	10342293
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

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 61 0 0 0 0 0 0 0 0999 V2000 -5.6456 -1.3266 -0.6186 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5587 -0.6012 -0.1226 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2714 -1.1001 -0.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0658 -2.2968 -0.9857 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7971 -2.7854 -1.1755 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5539 -3.9753 -1.8404 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6795 -4.6979 -2.3348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7318 -2.0614 -0.6846 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9330 -0.8611 -0.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2217 -0.3604 0.1871 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4295 0.9049 0.9202 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8806 1.1262 1.1918 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5760 2.1333 0.6926 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0201 2.3116 0.9918 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9054 3.1209 -0.1950 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1510 -0.1696 0.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 0.9326 1.0831 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4117 -0.7139 0.2346 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5228 -1.9071 -0.4409 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4652 -2.5449 -0.8791 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8026 -2.4336 -0.6536 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9115 -1.7629 -0.1925 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7646 -0.5652 0.4829 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5255 -0.0355 0.7004 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3482 1.1464 1.3646 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0058 0.1087 0.9558 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7297 0.7734 -0.1469 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9459 2.0670 -0.1012 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4773 2.9080 1.0485 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6767 2.7121 -1.2265 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1874 -2.3110 -0.4178 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7067 -2.2857 -0.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4478 -1.5564 -1.6873 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5649 -0.7029 -0.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9071 -2.8551 -1.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3608 -4.9983 -1.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2815 -3.9750 -2.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4026 -5.5168 -3.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9867 0.8388 1.9636 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0544 1.7825 0.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4225 0.4369 1.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5801 1.5278 0.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2089 2.1177 2.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3815 3.3211 0.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6859 2.5935 -1.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5994 3.9490 -0.4483 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0095 3.5782 0.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8729 -3.3838 -1.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1469 1.9995 0.8564 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8246 0.7507 1.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6827 -0.7202 1.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0722 0.1934 -0.9764 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9235 3.9119 0.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8388 2.5056 2.0195 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3684 2.9699 1.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0834 2.5333 -2.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7814 3.7940 -1.1234 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6341 2.1734 -1.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6513 -2.7182 0.3899 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 1 0 6 7 1 0 5 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 13 15 1 0 9 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 19 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 27 28 2 3 28 29 1 0 28 30 1 0 22 31 1 0 10 3 1 0 24 18 1 0 20 8 1 0 1 32 1 0 1 33 1 0 1 34 1 0 4 35 1 0 7 36 1 0 7 37 1 0 7 38 1 0 11 39 1 0 11 40 1 0 12 41 1 0 14 42 1 0 14 43 1 0 14 44 1 0 15 45 1 0 15 46 1 0 15 47 1 0 21 48 1 0 25 49 1 0 26 50 1 0 26 51 1 0 27 52 1 0 29 53 1 0 29 54 1 0 29 55 1 0 30 56 1 0 30 57 1 0 30 58 1 0 31 59 1 0 M END

Standard InCHIKey	PGWGLEHDWSDHBH-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C25H28O6/c1-13(2)7-9-15-17(26)11-19-22(23(15)27)24(28)21-16(10-8-14(3)4)18(29-5)12-20(30-6)25(21)31-19/h7-8,11-12,26-27H,9-10H2,1-6H3
SMILES	COc1cc(OC)c2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	424.19	Volume:	444.3 ? Van der Waals volume.
Dense:	0.955	LogP:	5.145 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.816 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.396 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	19.0
TPSA:	89.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.407	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.1	Fsp³:	0.32
MCE-18:	22.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.929	Fluc inhibitor:	0.276 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.969 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.828 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.232	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969	MDCK Permeability:	-4.649
Pgp-inhibitor:	0.991	Pgp-substrate:	0.153
PAMPA:	0.031 ? 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):	0.205
20% Bioavailability (F20%):	0.812	30% Bioavailability (F30%):	0.958
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.932
Plasma Protein Binding (PPB):	94.886%	Volume Distribution (VD):	0.272
Fu:	4.755% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.993
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.108	CYP2C9-substrate:	0.253
CYP2D6-inhibitor:	0.982	CYP2D6-substrate:	0.986
CYP3A4-inhibitor:	0.99	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

6.061

Half-life (T1/2):

1.052

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.565
Human Hepatotoxicity (H-HT):	0.548	Drug-induced Liver Injury (DILI):	0.676
AMES Toxicity:	0.699	Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.602	Skin Sensitization:	0.945
Carcinogencity:	0.618	Eye Corrosion:	0.0
Eye Irritation:	0.45	Respiratory Toxicity:	0.984
Drug-induced Neurotoxicity:	0.265	Ototoxicity:	0.395
Hematotoxicity:	0.208	Drug-induced Nephrotoxicity:	0.602
Genotoxicity:	0.956	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.427	Hek293 Cytotoxicity:	0.645
BCF:	2.223 ? 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:	4.879 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.512 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.951 ? 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
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	twig	n.a.	PMID[11908969]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO13263	Verbena brasiliensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6106	Hymeniacidon perlevis	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17438	Polygala virgata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18657	Galanthus gracilis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18005	Artemisia leucodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11770	Amphicome emodi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14950	Ardisia polycephala	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18995	Gaultheria itoana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19359	Parmotrema delicatulum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19560	Populus italica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19501	Pseudosuberites hyalinus	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO11770	Amphicome emodi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14950	Ardisia polycephala	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6106	Hymeniacidon perlevis	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18995	Gaultheria itoana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17438	Polygala virgata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19560	Populus italica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18657	Galanthus gracilis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18005	Artemisia leucodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19359	Parmotrema delicatulum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13263	Verbena brasiliensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19501	Pseudosuberites hyalinus	Species	Suberitidae	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
EC50	1

Activity Type	# Activity
Cell line	1

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
NPT91	Cell line	KB	Homo sapiens	EC50	=	1.5	ug.mL-1	PMID[11908969]

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 NPC217677 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	23983
0.1-0.2	21321
0.2-0.3	3953
0.3-0.4	487
0.4-0.5	81
0.5-0.6	24
0.6-0.7	6
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
0.6923	Remote Similarity	NPC228785
0.6923	Remote Similarity	NPC602307
0.6618	Remote Similarity	NPC236132
0.6027	Remote Similarity	NPC61010
0.6	Remote Similarity	NPC40491
0.6	Remote Similarity	NPC278052
0.5821	Remote Similarity	NPC142339
0.5811	Remote Similarity	NPC310349
0.5735	Remote Similarity	NPC100123
0.5676	Remote Similarity	NPC25152
0.5652	Remote Similarity	NPC119224
0.5634	Remote Similarity	NPC306488
0.5625	Remote Similarity	NPC602367
0.5432	Remote Similarity	NPC7483
0.5432	Remote Similarity	NPC74766
0.5395	Remote Similarity	NPC189473
0.5362	Remote Similarity	NPC186397
0.5333	Remote Similarity	NPC136674
0.5333	Remote Similarity	NPC602497
0.5278	Remote Similarity	NPC14353
0.5256	Remote Similarity	NPC37870
0.5139	Remote Similarity	NPC241904
0.5139	Remote Similarity	NPC165977
0.5135	Remote Similarity	NPC40942
0.5128	Remote Similarity	NPC262286
0.507	Remote Similarity	NPC157784
0.507	Remote Similarity	NPC24821
0.507	Remote Similarity	NPC284220
0.5068	Remote Similarity	NPC56085
0.5065	Remote Similarity	NPC236796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC217677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3723
0.1-0.2	5353
0.2-0.3	73
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
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
		NPD

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