NPASS Compound

Natural Product: NPC477919

Natural Product ID	NPC477919
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MRBLTWPEPGRXQN-PEVZUJSLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL490353
PubChem CID	13994830
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 56 59 0 0 0 0 0 0 0 0999 V2000 3.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1443 2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8943 3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1443 5.1106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 5.1106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9048 6.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3557 2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 -1.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 -0.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3442 -2.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6560 -3.6844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 -0.5932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2348 5.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7962 7.0581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0857 4.6595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1443 -0.0855 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8758 1.4481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0575 0.4910 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6059 2.1752 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4306 1.0401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0434 4.7758 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0434 2.8474 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0658 6.6086 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5538 5.6237 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1652 8.0651 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4703 7.0264 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4027 6.5094 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9915 5.0095 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0673 4.1490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2398 5.1710 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6137 1.6956 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5048 3.4767 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6764 0.5374 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6004 -0.7041 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8578 -2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3038 -1.8976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8158 -2.8825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0626 0.4027 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 -1.0497 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1443 2.5126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 0.5932 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5207 2.1683 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8384 -2.0865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0741 -2.7056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0826 -4.1480 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5471 -1.6902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2508 5.3405 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 6 8 1 0 8 9 1 0 9 10 1 0 11 10 1 6 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 13 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 17 21 1 6 6 22 1 0 22 23 2 0 22 24 1 0 8 2 1 0 18 11 1 0 16 2 1 0 16 11 1 0 1 25 1 0 1 26 1 0 1 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 7 34 1 0 7 35 1 0 7 36 1 0 8 37 1 1 9 38 1 0 9 39 1 0 10 40 1 0 10 41 1 0 12 42 1 0 12 43 1 0 13 44 1 1 14 45 1 0 14 46 1 0 15 47 1 0 15 48 1 0 16 49 1 1 18 50 1 0 18 51 1 0 19 52 1 0 19 53 1 0 20 54 1 0 21 55 1 0 24 56 1 0 M END

Standard InCHIKey	MRBLTWPEPGRXQN-PEVZUJSLSA-N
Standard InCHI	InChI=1S/C20H32O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h13-15,21,24H,3-12H2,1-2H3,(H,22,23)/t13-,14-,15-,17+,18+,19-,20-/m0/s1
SMILES	C[C@@]12CCC[C@](C)([C@H]1CC[C@]13C[C@H](CC[C@@H]23)[C@](C1)(CO)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	336.23	Volume:	352.775 ? Van der Waals volume.
Dense:	0.953	LogP:	1.971 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.187 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.204 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	20.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.723	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.644	Fsp³:	0.95
MCE-18:	106.974 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.067	Fluc inhibitor:	0.036 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.495	Promiscuous compounds:	0.306

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.48	MDCK Permeability:	-5.105
Pgp-inhibitor:	0.0	Pgp-substrate:	0.025
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):	0.004
20% Bioavailability (F20%):	0.034	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.176

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081	MRP1:	0.8
Plasma Protein Binding (PPB):	94.572%	Volume Distribution (VD):	-0.197
Fu:	7.478% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.512	BCRP inhibitor:	0.043
BSEP inhibitor:	0.709

ADMET: Metabolism

CYP1A2-inhibitor:	0.736	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.004	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.122	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.97	CYP3A4-substrate:	0.016
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

3.248

Half-life (T1/2):

1.658

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.019
Human Hepatotoxicity (H-HT):	0.538	Drug-induced Liver Injury (DILI):	0.085
AMES Toxicity:	0.228	Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.132	Skin Sensitization:	0.961
Carcinogencity:	0.773	Eye Corrosion:	0.278
Eye Irritation:	0.879	Respiratory Toxicity:	0.486
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.664
Hematotoxicity:	0.554	Drug-induced Nephrotoxicity:	0.892
Genotoxicity:	0.044	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.025
BCF:	0.773 ? 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:	3.581 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.124 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.271 ? 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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6333	Annona glabra	Species	Annonaceae	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	9
Inhibition	7
Ratio IC50	2

Activity Type	# Activity
Individual protein	4
Cell line	2
Non-molecular	5
Others	7

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1138	Individual protein	11-beta-hydroxysteroid dehydrogenase 2	Homo sapiens	IC50	>	1000000.0	nM	PMID[23747808]
NPT1137	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	IC50	=	1236.0	nM	PMID[23747808]
NPT4862	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	3216.0	nM	PMID[23747808]
NPT4861	Individual protein	11-beta-hydroxysteroid dehydrogenase 2	Mus musculus	IC50	>	1000000.0	nM	PMID[23747808]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[19928884]
NPT319	Cell line	B16	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[19928884]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	7.2	%	PMID[12398544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	2.3	%	PMID[12398544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.9	%	PMID[12398544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.4	%	PMID[12398544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[19928884]
NPT2	Others	Unspecified	n.a.	Inhibition	=	46.0	%	PMID[9584397]
NPT2	Others	Unspecified	n.a.	Ratio IC50	>	809.0	n.a.	PMID[23747808]
NPT2	Others	Unspecified	n.a.	Ratio IC50	>	311.0	n.a.	PMID[23747808]
NPT2	Others	Unspecified	n.a.	Inhibition	=	89.16	%	PMID[24997688]
NPT2	Others	Unspecified	n.a.	IC50	=	3.63	ug.mL-1	PMID[24997688]
NPT2	Others	Unspecified	n.a.	Inhibition	=	70.82	%	PMID[24997688]
NPT2	Others	Unspecified	n.a.	IC50	=	4.34	ug.mL-1	PMID[24997688]

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 NPC477919 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	25598
0.1-0.2	22197
0.2-0.3	1776
0.3-0.4	178
0.4-0.5	70
0.5-0.6	27
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180199
0.7069	Intermediate Similarity	NPC477935
0.6786	Remote Similarity	NPC472272
0.6786	Remote Similarity	NPC479106
0.6786	Remote Similarity	NPC479107
0.6724	Remote Similarity	NPC480086
0.6415	Remote Similarity	NPC252032
0.6415	Remote Similarity	NPC319671
0.6415	Remote Similarity	NPC476734
0.629	Remote Similarity	NPC609700
0.6078	Remote Similarity	NPC604769
0.5965	Remote Similarity	NPC607026
0.5818	Remote Similarity	NPC268736
0.5818	Remote Similarity	NPC477931
0.5769	Remote Similarity	NPC243469
0.5769	Remote Similarity	NPC475943
0.5769	Remote Similarity	NPC190827
0.566	Remote Similarity	NPC63190
0.5636	Remote Similarity	NPC330659
0.5636	Remote Similarity	NPC24014
0.5636	Remote Similarity	NPC27349
0.5636	Remote Similarity	NPC244708
0.5636	Remote Similarity	NPC161187
0.5439	Remote Similarity	NPC170985
0.5424	Remote Similarity	NPC215893
0.537	Remote Similarity	NPC130459
0.537	Remote Similarity	NPC474221
0.5345	Remote Similarity	NPC199965
0.5345	Remote Similarity	NPC477930
0.5345	Remote Similarity	NPC476732
0.5179	Remote Similarity	NPC472854
0.5179	Remote Similarity	NPC165124
0.5179	Remote Similarity	NPC479247
0.5161	Remote Similarity	NPC259173
0.5147	Remote Similarity	NPC477936
0.5085	Remote Similarity	NPC212661
0.5085	Remote Similarity	NPC471035
0.5082	Remote Similarity	NPC472311

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6148
0.1-0.2	2915
0.2-0.3	86
0.3-0.4	0
0.4-0.5	0
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
0.5439	Remote Similarity	NPD4224	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