NPASS Compound

Natural Product: NPC483889

Natural Product ID	NPC483889
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BRFDWBSAUKGYTR-RLDPOOHYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44361772
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 93 98 0 0 0 0 0 0 0 0999 V2000 -5.9853 -2.9362 1.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6231 -2.5929 2.0783 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3437 -2.4149 3.2877 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.4486 1.1694 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2551 -2.1196 1.5816 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3279 -3.1900 1.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4188 -2.6154 0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3992 -1.6405 0.9354 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4504 -0.4265 1.1384 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2861 -0.0365 2.6132 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9370 -0.7612 1.0030 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4540 -0.5961 -0.2892 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4707 0.2492 -0.6419 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0118 0.9542 0.2341 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9666 0.3675 -2.0290 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4164 -0.3855 -3.0433 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9167 -0.2499 -4.3437 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9433 0.6190 -4.6198 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5050 1.3803 -3.6176 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9952 1.2311 -2.3368 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1604 0.6891 0.2284 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8985 0.4827 -0.8313 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0926 -0.1019 -0.1142 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7709 -1.4921 0.3982 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7872 -1.7538 1.4838 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0785 -2.4421 -0.5897 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2799 -0.1224 -0.8223 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4626 0.4843 -0.4459 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4842 1.1097 0.6163 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6113 0.3435 -1.3312 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5361 -0.3394 -2.5227 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6380 -0.4891 -3.3753 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8437 0.0673 -3.0092 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9110 0.7499 -1.8144 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8244 0.8988 -0.9717 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3026 1.6401 -1.4648 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2393 1.9625 -2.8042 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7497 1.1040 -3.5799 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7332 3.2837 -3.3245 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0120 1.9371 0.8860 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7628 3.0334 0.6729 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6644 2.8887 -0.1599 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5867 4.3115 1.3502 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4355 5.3711 1.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2918 6.5952 1.6944 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2746 6.7950 2.6289 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5370 5.7532 2.8831 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3997 4.5476 2.2741 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4676 -2.2799 2.1991 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2329 -3.4357 2.1817 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5410 -4.6775 1.8247 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8792 -3.7091 3.5382 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9615 -3.4396 0.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4158 -3.6813 2.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6844 -2.0806 1.6261 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2933 -2.0237 2.6966 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8211 -4.1185 0.8340 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2224 -3.4671 -0.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8922 -2.1564 -0.7824 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5203 -0.6040 3.1069 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1009 1.0184 2.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2047 -0.2966 3.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4834 -0.0403 1.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6187 -1.0643 -2.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5150 -0.8197 -5.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3377 0.7308 -5.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3146 2.0549 -3.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4184 1.8128 -1.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0632 0.8789 -0.3854 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4793 -0.2120 -1.5773 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2682 0.5121 0.7925 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6734 -1.1055 2.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7634 -2.8118 1.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8283 -1.6088 1.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5636 -2.3245 -1.4209 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6083 -0.7756 -2.8205 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5703 -1.0264 -4.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7190 -0.0432 -3.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8556 1.2077 -1.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9239 1.4477 -0.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0848 3.5861 -4.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8392 4.0258 -2.5303 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7301 3.0472 -3.7843 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2483 5.2860 0.3588 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9332 7.4366 1.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1235 7.7265 3.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0914 3.7614 2.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1097 -4.9621 2.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2016 -5.4816 1.6172 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3057 -4.5543 1.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7877 -4.2976 3.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1541 -4.3360 4.1018 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0200 -2.7939 4.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 9 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 6 23 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 22 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 21 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 8 49 1 0 49 50 1 0 50 51 1 0 50 52 1 0 11 5 1 0 20 15 1 0 35 30 1 0 48 43 1 0 50 6 1 0 24 8 1 0 1 53 1 0 1 54 1 0 1 55 1 0 5 56 1 1 6 57 1 0 7 58 1 0 7 59 1 0 10 60 1 0 10 61 1 0 10 62 1 0 11 63 1 1 16 64 1 0 17 65 1 0 18 66 1 0 19 67 1 0 20 68 1 0 21 69 1 6 22 70 1 6 23 71 1 1 25 72 1 0 25 73 1 0 25 74 1 0 26 75 1 0 31 76 1 0 32 77 1 0 33 78 1 0 34 79 1 0 35 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 48 87 1 0 51 88 1 0 51 89 1 0 51 90 1 0 52 91 1 0 52 92 1 0 52 93 1 0 M END

Standard InCHIKey	BRFDWBSAUKGYTR-RLDPOOHYSA-N
Standard InCHI	InChI=1S/C39H41NO12/c1-22(41)47-28-27-20-39(52-36(27,3)4)37(5,30(28)49-33(43)24-14-9-7-10-15-24)31(50-35(45)26-18-13-19-40-21-26)29(48-23(2)42)32(38(39,6)46)51-34(44)25-16-11-8-12-17-25/h7-19,21,27-32,46H,20H2,1-6H3/t27?,28-,29+,30-,31-,32-,37+,38-,39?/m0/s1
SMILES	CC(=O)O[C@H]1C2CC3([C@](C)([C@H]1OC(=O)c1ccccc1)[C@H]([C@H]([C@@H]([C@]3(C)O)OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1cccnc1)OC2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	715.26	Volume:	711.33 ? Van der Waals volume.
Dense:	1.006	LogP:	3.449 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.201 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.447 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	37.0
TPSA:	173.85 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.259	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.995	Fsp³:	0.436
MCE-18:	193.286 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.311	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.371 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.035	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.375	MDCK Permeability:	-4.874
Pgp-inhibitor:	1.0	Pgp-substrate:	0.338
PAMPA:	0.379 ? 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%):	0.288	30% Bioavailability (F30%):	0.737
50% Bioavailability (F50%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	88.762%	Volume Distribution (VD):	-0.125
Fu:	9.84% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.865	BCRP inhibitor:	0.005
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.196	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.951 ? 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):

5.539

Half-life (T1/2):

0.53

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.47
Human Hepatotoxicity (H-HT):	0.048	Drug-induced Liver Injury (DILI):	0.477
AMES Toxicity:	0.072	Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.17	Skin Sensitization:	0.862
Carcinogencity:	0.442	Eye Corrosion:	0.0
Eye Irritation:	0.103	Respiratory Toxicity:	0.034
Drug-induced Neurotoxicity:	0.2	Ototoxicity:	0.366
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.578
Genotoxicity:	0.163	RPMI-8226 Immunitoxicity:	0.015
A549 Cytotoxicity:	0.047	Hek293 Cytotoxicity:	0.139
BCF:	0.685 ? 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:	3.601 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.051 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.61 ? 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
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11741484]
NPO10966	Maytenus chubutensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11741484]
NPO10966	Maytenus chubutensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3859	Maytenus magellanica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10966	Maytenus chubutensis	Species	Celastraceae	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
Inhibition	6

Activity Type	# Activity
Others	6

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
NPT2	Others	Unspecified	n.a.	Inhibition	=	19.7	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	69.7	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	12.9	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	44.0	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	0.0	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	21.4	%	PMID[11741484]

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 NPC483889 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	14039
0.1-0.2	33633
0.2-0.3	1578
0.3-0.4	463
0.4-0.5	116
0.5-0.6	18
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9028	High Similarity	NPC483881
0.7714	Intermediate Similarity	NPC152440
0.7714	Intermediate Similarity	NPC483888
0.7222	Intermediate Similarity	NPC483882
0.6951	Remote Similarity	NPC127026
0.6951	Remote Similarity	NPC483890
0.6333	Remote Similarity	NPC483891
0.6129	Remote Similarity	NPC483880
0.6129	Remote Similarity	NPC156941
0.5862	Remote Similarity	NPC301368
0.5862	Remote Similarity	NPC84815
0.5783	Remote Similarity	NPC481071
0.5765	Remote Similarity	NPC483887
0.5765	Remote Similarity	NPC158020
0.575	Remote Similarity	NPC472576
0.5618	Remote Similarity	NPC483871
0.5568	Remote Similarity	NPC610927
0.5517	Remote Similarity	NPC212768
0.5517	Remote Similarity	NPC4421
0.5517	Remote Similarity	NPC608007
0.5333	Remote Similarity	NPC473089
0.5333	Remote Similarity	NPC6576
0.5233	Remote Similarity	NPC127720
0.5169	Remote Similarity	NPC276735
0.5111	Remote Similarity	NPC25768
0.5055	Remote Similarity	NPC611111
0.5053	Remote Similarity	NPC483885

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3188
0.1-0.2	5804
0.2-0.3	153
0.3-0.4	5
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