NPASS Compound

Natural Product: NPC287075

Natural Product ID	NPC287075
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Roridin M
IUPAC Name	n.a.
Synonyms	Roridin M
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL435984
PubChem CID	11813411
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

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 74 79 0 0 0 0 0 0 0 0999 V2000 4.9293 2.4899 2.7528 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2172 1.9556 1.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6767 1.0328 0.7558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8423 0.6035 -0.3773 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3738 0.3725 -0.0458 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0147 1.1421 1.1941 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8133 2.4528 1.2640 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6133 0.8800 -1.2218 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2967 1.1323 -1.1589 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5005 2.1104 -0.6713 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0584 3.1124 -0.1495 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9821 2.0204 -0.7424 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8519 2.8891 -0.3573 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4237 4.2118 0.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3059 2.6677 -0.3858 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7970 1.3442 -0.8043 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7282 0.4500 0.2899 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2748 -0.6879 -0.3641 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7402 -0.5529 -0.6031 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5484 -0.6528 -1.7136 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2808 -1.5050 -1.4101 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3791 -2.7092 -0.9835 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5216 -3.7425 -0.6040 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2485 -3.8971 -0.5087 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3093 -2.8766 -0.8185 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6321 -1.7977 -1.2099 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0788 -3.0712 -0.6785 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8841 -1.9199 -1.0333 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2177 -2.4776 -1.4845 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2501 -1.6827 -0.6564 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4761 -1.6640 0.6665 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0694 -1.6922 1.8875 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5047 -2.8756 1.3277 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1659 -1.1171 0.1925 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1545 -1.3900 1.2827 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4077 -0.4142 -1.1255 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4285 -2.3045 -2.8393 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2147 0.6752 -1.8277 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1605 2.8970 3.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5163 3.3880 2.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5819 1.7532 3.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6600 0.6302 0.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8691 1.4998 -1.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3690 0.5924 2.1196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9391 1.2672 1.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4023 3.0583 2.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7509 2.9203 0.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9634 0.4007 -2.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1082 1.9347 -1.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3117 1.1174 -1.1759 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2930 4.8907 0.3057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 3.9880 1.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7057 4.7301 -0.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8076 3.4362 -1.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6496 2.8239 0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9430 1.3917 -0.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9991 -1.5285 0.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2338 0.2013 0.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1994 -1.5433 -0.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9596 -0.4249 -1.6746 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0972 -1.1038 -2.5237 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4263 -0.9226 -1.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4779 -3.0660 -0.8850 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0553 -4.7143 -0.2922 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8281 -4.8265 -0.1840 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3553 -1.4011 -1.8427 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3571 -3.5346 -1.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1827 -2.2459 -0.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5909 -1.3460 2.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1944 -1.6902 2.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9560 -2.4935 1.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2351 -0.8028 1.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5961 -1.2637 2.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5704 -2.5252 -3.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 1 6 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 34 35 1 1 30 36 1 0 29 37 1 0 20 38 1 0 7 2 1 0 38 16 1 0 36 4 1 0 34 5 1 0 34 28 1 0 31 33 1 6 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 4 43 1 6 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 12 50 1 0 14 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 6 18 57 1 1 19 58 1 0 19 59 1 0 19 60 1 0 20 61 1 6 21 62 1 0 22 63 1 0 23 64 1 0 24 65 1 0 28 66 1 6 29 67 1 6 30 68 1 1 32 69 1 0 32 70 1 0 35 71 1 0 35 72 1 0 35 73 1 0 37 74 1 0 M END

Standard InCHIKey	DRYUAYDRFAXIBH-DVLKMXNNSA-N
Standard InCHI	InChI=1S/C29H36O9/c1-16-9-10-28-14-33-22(31)12-17(2)13-23-35-18(3)19(36-23)7-5-6-8-21(30)38-25-24(32)26(37-20(28)11-16)29(15-34-29)27(25,28)4/h5-8,11-12,18-20,23-26,32H,9-10,13-15H2,1-4H3/b7-5+,8-6-,17-12+/t18-,19-,20+,23+,24+,25+,26+,27+,28+,29-/m0/s1
SMILES	CC1=C[C@@H]2[C@@]3(CC1)COC(=O)/C=C(C)/C[C@@H]1O[C@@H](C)[C@H](/C=C/C=CC(=O)O[C@@H]4[C@H]([C@H]([C@@]5(CO5)[C@@]34C)O2)O)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.24	Volume:	522.095 ? Van der Waals volume.
Dense:	1.012	LogP:	1.189 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.672 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.829 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	38.0
TPSA:	113.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.288	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.9	Fsp³:	0.655
MCE-18:	137.75 ? 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:	0.929	Fluc inhibitor:	0.031 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.165 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.036 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.169	Promiscuous compounds:	0.467

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.672	MDCK Permeability:	-5.081
Pgp-inhibitor:	0.042	Pgp-substrate:	0.872
PAMPA:	0.986 ? 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):	0.0
20% Bioavailability (F20%):	0.015	30% Bioavailability (F30%):	0.039
50% Bioavailability (F50%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.544
Plasma Protein Binding (PPB):	93.716%	Volume Distribution (VD):	0.093
Fu:	5.016% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.712	BCRP inhibitor:	0.266
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.083	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.037	CYP3A4-substrate:	0.939
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.406
HLM stability:	0.92 ? 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):

4.741

Half-life (T1/2):

2.669

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.08
Human Hepatotoxicity (H-HT):	0.992	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.667
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	1.0
Carcinogencity:	0.552	Eye Corrosion:	0.0
Eye Irritation:	0.678	Respiratory Toxicity:	0.939
Drug-induced Neurotoxicity:	0.872	Ototoxicity:	0.855
Hematotoxicity:	0.849	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.956
A549 Cytotoxicity:	0.896	Hek293 Cytotoxicity:	0.863
BCF:	0.824 ? 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:	3.595 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.492 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.765 ? 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
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075777]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13678412]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539317]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30443	Myrothecium verrucaria	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

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
Concentration	1
Selectivity	5
IC50	17

Activity Type	# Activity
Cell line	21
Non-molecular	2

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
NPT730	Cell line	MC-38	Mus musculus	Selectivity	=	0.0	zone unit	PMID[13678412]
NPT730	Cell line	MC-38	Mus musculus	Selectivity	=	100.0	zone unit	PMID[13678412]
NPT137	Cell line	L1210	Mus musculus	Selectivity	=	100.0	zone unit	PMID[13678412]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	>	10000.0	nM	PMID[16643031]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[21800859]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	>	10000.0	nM	PMID[21800859]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[16643031]
NPT405	Cell line	NCI-H226	Homo sapiens	IC50	=	157.0	nM	PMID[16643031]
NPT455	Cell line	NCI-H522	Homo sapiens	IC50	=	26.0	nM	PMID[16643031]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	75.0	nM	PMID[19128055]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	483.0	nM	PMID[16643031]
NPT387	Cell line	M14	Homo sapiens	IC50	=	75.0	nM	PMID[16643031]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	=	260.0	nM	DrugMatrix in vitro pharmacology data
NPT398	Cell line	UACC-62	Homo sapiens	IC50	=	409.0	nM	PMID[26264503]
NPT401	Cell line	786-0	Homo sapiens	IC50	>	10000.0	nM	PMID[26386821]
NPT376	Cell line	A498	Homo sapiens	IC50	=	583.0	nM	PMID[26386821]
NPT406	Cell line	RXF 393	Homo sapiens	IC50	=	2180.0	nM	PMID[26264503]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[26264503]
NPT400	Cell line	MDA-MB-435	Homo sapiens	IC50	=	137.0	nM	PMID[26264503]
NPT367	Cell line	MDA-N	Homo sapiens	IC50	=	83.0	nM	PMID[26264503]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Concentration	=	41.0	ug ml-1	PMID[13678412]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Selectivity	=	-150.0	zone unit	PMID[13678412]
NPT22117	Cell line	NCI-H125	Homo sapiens	Selectivity	=	-100.0	zone unit	PMID[13678412]

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 NPC287075 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	20576
0.1-0.2	28032
0.2-0.3	1180
0.3-0.4	17
0.4-0.5	42
0.5-0.6	6
0.6-0.7	5
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
0.6974	Remote Similarity	NPC265502
0.6875	Remote Similarity	NPC469960
0.6875	Remote Similarity	NPC93026
0.6111	Remote Similarity	NPC240838
0.6111	Remote Similarity	NPC600295
0.5526	Remote Similarity	NPC605097
0.5435	Remote Similarity	NPC471082
0.5263	Remote Similarity	NPC79631
0.5169	Remote Similarity	NPC13743
0.5111	Remote Similarity	NPC29389
0.5111	Remote Similarity	NPC112316

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC287075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7433
0.1-0.2	1694
0.2-0.3	23
0.3-0.4	0
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