NPASS Compound

Natural Product: NPC472053

Natural Product ID	NPC472053
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IXBPWSPJMNOFJJ-IZDSXESFSA-N
IUPAC Name	n.a.
Synonyms	Alterporriol D; Alterporriol E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3335041
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

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 78 83 0 0 0 0 0 0 0 0999 V2000 -3.4992 3.7373 -0.9183 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0713 2.5623 -1.6929 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3143 2.1141 -0.9722 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0541 1.2060 0.1723 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8740 0.3609 0.0947 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9734 0.4812 -0.8394 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0747 1.4817 -1.8938 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8089 2.1045 -2.0185 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7784 -0.3984 -0.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9140 -0.2806 -1.7902 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5959 -1.4277 0.1243 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5580 -1.5613 1.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7119 -0.6694 1.1291 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5702 -0.8131 2.0526 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4284 -2.5184 2.1075 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3225 -3.3359 2.0637 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3631 -3.2008 1.0606 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4912 -2.2414 0.0773 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4912 -2.0691 -0.9884 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4146 -2.7326 -2.1958 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3572 -2.5564 -3.1965 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4169 -1.7000 -3.0151 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4955 -1.0345 -1.8069 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5529 -1.2085 -0.8018 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7003 -0.4720 0.4489 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8330 -0.6509 1.3368 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8212 0.4510 0.6748 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7001 0.5921 -0.3044 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5965 -0.1210 -1.5713 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4521 0.0415 -2.4747 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8618 1.5096 -0.1481 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2611 1.5256 1.2885 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1260 1.9102 2.2066 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8765 1.1411 1.9653 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7611 1.9828 2.0901 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8192 3.3914 2.0306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5350 1.7168 3.5252 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2750 2.5002 1.4389 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4699 2.8037 -0.5261 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3909 -1.4879 -3.9897 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6630 -3.5962 -2.3656 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8401 -4.3193 -3.5473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7590 -4.0143 0.9980 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0553 -5.0341 1.9015 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4015 -2.6374 3.1042 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1112 1.9005 1.3965 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9157 3.2850 -0.4531 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4633 3.0512 -2.9386 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2976 4.4530 -0.7104 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7548 4.2181 -1.5822 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9628 3.3901 -0.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0370 1.7217 -1.7125 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9444 0.5077 0.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2351 0.9262 -2.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4747 2.3748 -1.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2091 -4.0939 2.8299 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2886 -3.0813 -4.1401 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7323 1.1617 -0.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7279 0.5658 1.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7276 0.3524 2.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3380 2.0840 1.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5996 3.8885 2.9976 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9258 3.5438 1.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6764 3.9324 1.5636 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2520 2.3622 3.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0068 2.3264 0.7864 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0694 3.0906 -1.2646 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1714 -2.1487 -4.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8854 -4.6922 -3.5903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6540 -3.6473 -4.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1000 -5.1479 -3.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1799 -5.0892 1.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7593 -6.0469 1.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6841 -4.8682 2.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2624 -3.1472 2.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0626 2.0444 1.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8916 3.2133 -0.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5915 4.0359 -2.9348 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 6 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 12 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 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 2 0 28 29 1 0 29 30 2 0 28 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 33 37 1 0 32 38 1 0 31 39 1 0 22 40 1 0 20 41 1 0 41 42 1 0 17 43 1 0 43 44 1 0 15 45 1 0 4 46 1 0 3 47 1 0 2 48 1 0 7 2 1 0 13 5 1 0 18 11 1 0 24 19 1 0 29 23 1 0 34 27 1 0 1 49 1 0 1 50 1 0 1 51 1 0 3 52 1 0 4 53 1 0 7 54 1 0 8 55 1 0 16 56 1 0 21 57 1 0 31 58 1 0 32 59 1 0 34 60 1 0 35 61 1 0 36 62 1 0 36 63 1 0 36 64 1 0 37 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 42 69 1 0 42 70 1 0 42 71 1 0 44 72 1 0 44 73 1 0 44 74 1 0 45 75 1 0 46 76 1 0 47 77 1 0 48 78 1 0 M END

Standard InCHIKey	IXBPWSPJMNOFJJ-IZDSXESFSA-N
Standard InCHI	InChI=1S/C32H30O16/c1-31(45)27(41)19-17(25(39)29(31)43)21(35)11-7(33)5-9(47-3)13(15(11)23(19)37)14-10(48-4)6-8(34)12-16(14)24(38)20-18(22(12)36)26(40)30(44)32(2,46)28(20)42/h5-6,25-30,33-34,39-46H,1-4H3/t25-,26+,27+,28-,29+,30-,31-,32+
SMILES	CC1(C(C(C2=C(C1O)C(=O)C3=C(C2=O)C(=CC(=C3C4=C(C=C(C5=C4C(=O)C6=C(C5=O)C(C(C(C6O)(C)O)O)O)O)OC)OC)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	670.15	Volume:	619.695 ? Van der Waals volume.
Dense:	1.081	LogP:	0.652 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.071 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.147 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	289.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.166	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.178	Fsp³:	0.375
MCE-18:	161.455 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.27	Fluc inhibitor:	0.068 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.202 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.632 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.26	Promiscuous compounds:	0.219

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.731	MDCK Permeability:	-4.8
Pgp-inhibitor:	0.0	Pgp-substrate:	0.004
PAMPA:	1.0 ? 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):	1.0
20% Bioavailability (F20%):	0.026	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.521
Plasma Protein Binding (PPB):	83.911%	Volume Distribution (VD):	-0.094
Fu:	16.227% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.511
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.087
HLM stability:	0.002 ? 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):

1.557

Half-life (T1/2):

4.696

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.204
Human Hepatotoxicity (H-HT):	0.694	Drug-induced Liver Injury (DILI):	0.906
AMES Toxicity:	0.921	Rat Oral Acute Toxicity:	0.519
Maximum Recommended Daily Dose:	0.945	Skin Sensitization:	0.097
Carcinogencity:	0.793	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.234
Drug-induced Neurotoxicity:	0.126	Ototoxicity:	0.998
Hematotoxicity:	0.463	Drug-induced Nephrotoxicity:	0.91
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.605
A549 Cytotoxicity:	0.269	Hek293 Cytotoxicity:	0.813
BCF:	0.807 ? 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:	3.383 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.164 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.184 ? 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
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Mentha pulegium	n.a.	n.a.	PMID[19271717]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271717]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23664494]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	isolated from fresh Juncus acutus	Lake Wadi el Natrun, Egypt	2012-NOV	PMID[25010124]
NPO33215	Stemphylium sp. 33231	Species	Pleosporaceae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25136754]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33215	Stemphylium sp. 33231	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	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	2
MIC	14
IC50	4

Activity Type	# Activity
Cell line	5
Organism	14
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
NPT1864	Cell line	L5178Y	Mus musculus	EC50	=	2.27	ug.mL-1	PMID[22691179]
NPT1864	Cell line	L5178Y	Mus musculus	Activity	=	64.8	%	PubChem BioAssay data set
NPT1864	Cell line	L5178Y	Mus musculus	Activity	=	92.1	%	PMID[18195064]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[8388433]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[25136754]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10000.0	nM	PMID[19344127]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5000.0	nM	PMID[17850214]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	7500.0	nM	PMID[18183025]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5000.0	nM	PMID[9677274]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10000.0	nM	PMID[19053514]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	2500.0	nM	PMID[22444684]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	10000.0	nM	PMID[22687439]
NPT3146	Organism	Micrococcus	Micrococcus	MIC	>	10000.0	nM	PMID[15646539]
NPT1238	Organism	Staphylococcus	Staphylococcus	MIC	>	10000.0	nM	PMID[18070958]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	>	10000.0	nM	PMID[8254344]

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 NPC472053 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	10637
0.1-0.2	35619
0.2-0.3	3506
0.3-0.4	76
0.4-0.5	9
0.5-0.6	5
0.6-0.7	4
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
0.7627	Intermediate Similarity	NPC600525
0.7031	Intermediate Similarity	NPC234497
0.6909	Remote Similarity	NPC472059
0.6604	Remote Similarity	NPC155686
0.6604	Remote Similarity	NPC602483
0.6471	Remote Similarity	NPC324522
0.5625	Remote Similarity	NPC477991
0.5345	Remote Similarity	NPC605299
0.5345	Remote Similarity	NPC607459
0.5238	Remote Similarity	NPC477992
0.5139	Remote Similarity	NPC472057

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3489
0.1-0.2	5609
0.2-0.3	52
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