NPASS Compound

Natural Product: NPC483887

Natural Product ID	NPC483887
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BQVGZDYZYXCBOZ-PUBGVOABSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44361714
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 92 97 0 0 0 0 0 0 0 0999 V2000 1.1214 -2.9914 -3.7405 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8741 -1.6133 -3.0996 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1474 -1.1669 -2.5295 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2353 -1.1451 -1.0492 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9379 -0.4345 -0.5781 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1535 -1.4213 -0.7758 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3070 -2.8364 -0.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4371 -1.1552 -0.0773 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6819 -1.5461 -0.8450 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6403 -1.3819 -2.3091 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3943 -0.6120 -2.7879 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3543 -1.5707 -2.2810 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9462 -2.8581 -2.4150 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2041 -2.7374 -2.8956 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3581 -2.6488 -4.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1256 -3.8292 -2.3783 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4566 0.6400 -2.2378 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5604 1.8087 -2.9780 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5935 1.6866 -4.2179 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6236 3.0862 -2.2471 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7398 -0.7103 -0.3477 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8735 -1.2165 0.2613 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9520 -2.4843 0.3701 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9449 -0.3317 0.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5745 0.1357 0.4941 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7840 0.3642 1.8595 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8452 -0.6711 2.5733 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9222 1.7027 2.4180 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1297 1.8275 3.7735 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2695 3.0817 4.3742 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2013 4.2070 3.6167 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9946 4.1124 2.2583 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8576 2.8568 1.6771 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1163 0.0637 0.7229 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2658 1.4244 0.9616 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2320 2.1651 -0.0549 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4512 2.0045 2.2726 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5896 3.3632 2.4083 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7698 3.9669 3.6498 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8122 3.1868 4.7844 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6751 1.8203 4.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4946 1.2328 3.4085 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3087 -0.4349 -0.5193 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2705 -0.9641 0.3270 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1097 -2.1696 0.5977 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3812 -0.2105 0.8694 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2737 -0.8464 1.6992 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3644 -0.1670 2.2513 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5626 1.1656 1.9682 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6801 1.7707 1.1552 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6098 1.1191 0.6086 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4578 -2.9001 -4.7937 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2653 -3.6550 -3.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9922 -3.4822 -3.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6575 -0.9576 -4.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4150 -0.1231 -2.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0243 -1.7798 -2.8964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2915 -2.1772 -0.6791 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8905 0.4292 -1.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 -2.8106 0.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7557 -3.3975 -1.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6482 -3.4054 -0.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5045 -1.8434 0.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0044 -2.5847 -0.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5498 -1.0236 -2.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4276 -0.5750 -3.8950 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6371 -3.6481 -4.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1785 -1.9304 -4.6188 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4451 -2.3390 -4.9185 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5957 -4.3508 -1.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1149 -3.4580 -2.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2281 -4.5827 -3.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7827 3.9574 -2.9152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5473 3.0220 -1.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7774 3.2087 -1.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7002 0.0253 1.7843 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9184 -0.8568 0.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0490 0.5467 0.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1915 0.9693 4.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4329 3.1824 5.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3055 5.2164 4.0437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9419 5.0249 1.6610 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6984 2.7961 0.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5623 4.0148 1.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8798 5.0314 3.7719 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9549 3.6617 5.7704 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 1.2190 5.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3896 0.1581 3.3461 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1904 -1.8863 1.9702 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0715 -0.6818 2.9122 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4157 1.7099 2.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9321 1.6376 -0.0329 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 1 0 6 7 1 1 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 11 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 9 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 8 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 5 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 4 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 12 2 1 0 33 28 1 0 42 37 1 0 51 46 1 0 12 6 1 0 14 10 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 6 3 56 1 0 3 57 1 0 4 58 1 1 5 59 1 6 7 60 1 0 7 61 1 0 7 62 1 0 8 63 1 1 9 64 1 6 10 65 1 0 11 66 1 6 15 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 16 72 1 0 20 73 1 0 20 74 1 0 20 75 1 0 24 76 1 0 24 77 1 0 24 78 1 0 29 79 1 0 30 80 1 0 31 81 1 0 32 82 1 0 33 83 1 0 38 84 1 0 39 85 1 0 40 86 1 0 41 87 1 0 42 88 1 0 47 89 1 0 48 90 1 0 49 91 1 0 51 92 1 0 M END

Standard InCHIKey	BQVGZDYZYXCBOZ-PUBGVOABSA-N
Standard InCHI	InChI=1S/C39H41NO11/c1-22-20-28(48-36(45)27-18-13-19-40-21-27)31(49-34(43)25-14-9-7-10-15-25)38(6)33(50-35(44)26-16-11-8-12-17-26)30(46-23(2)41)29-32(47-24(3)42)39(22,38)51-37(29,4)5/h7-19,21-22,28-33H,20H2,1-6H3/t22-,28-,29?,30+,31+,32-,33+,38+,39?/m1/s1
SMILES	C[C@@H]1C[C@H]([C@@H]([C@@]2(C)[C@H]([C@H](C3[C@H](C12OC3(C)C)OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)c1cccnc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	699.27	Volume:	702.54 ? Van der Waals volume.
Dense:	0.995	LogP:	3.013 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.121 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.787 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	37.0
TPSA:	153.62 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.226	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.923	Fsp³:	0.436
MCE-18:	184.5 ? 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:	0.537	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.454 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.043	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.195	MDCK Permeability:	-4.823
Pgp-inhibitor:	1.0	Pgp-substrate:	0.038
PAMPA:	0.268 ? 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%):	0.138	30% Bioavailability (F30%):	0.338
50% Bioavailability (F50%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	1.0
Plasma Protein Binding (PPB):	90.462%	Volume Distribution (VD):	-0.099
Fu:	9.551% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.007
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.421
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.361
CYP3A4-inhibitor:	0.198	CYP3A4-substrate:	0.441
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.975 ? 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):

4.208

Half-life (T1/2):

0.551

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.731
Human Hepatotoxicity (H-HT):	0.038	Drug-induced Liver Injury (DILI):	0.955
AMES Toxicity:	0.346	Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.19	Skin Sensitization:	0.994
Carcinogencity:	0.684	Eye Corrosion:	0.0
Eye Irritation:	0.28	Respiratory Toxicity:	0.051
Drug-induced Neurotoxicity:	0.757	Ototoxicity:	0.144
Hematotoxicity:	0.028	Drug-induced Nephrotoxicity:	0.432
Genotoxicity:	0.048	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.254	Hek293 Cytotoxicity:	0.341
BCF:	0.861 ? 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:	3.844 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.208 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.915 ? 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	=	13.3	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	94.5	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	13.0	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	79.3	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	1.7	%	PMID[11741484]
NPT2	Others	Unspecified	n.a.	Inhibition	=	42.2	%	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 NPC483887 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	21297
0.1-0.2	26813
0.2-0.3	1292
0.3-0.4	264
0.4-0.5	130
0.5-0.6	44
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
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	NPC158020
0.8472	Intermediate Similarity	NPC608007
0.7273	Intermediate Similarity	NPC212768
0.7273	Intermediate Similarity	NPC4421
0.7143	Intermediate Similarity	NPC481047
0.7143	Intermediate Similarity	NPC481045
0.6386	Remote Similarity	NPC301368
0.6386	Remote Similarity	NPC84815
0.631	Remote Similarity	NPC473115
0.631	Remote Similarity	NPC75600
0.631	Remote Similarity	NPC483884
0.6203	Remote Similarity	NPC609924
0.6173	Remote Similarity	NPC481050
0.6071	Remote Similarity	NPC610927
0.6	Remote Similarity	NPC66761
0.6	Remote Similarity	NPC483843
0.6	Remote Similarity	NPC476094
0.5976	Remote Similarity	NPC609221
0.5974	Remote Similarity	NPC473060
0.5974	Remote Similarity	NPC51314
0.5926	Remote Similarity	NPC481071
0.5823	Remote Similarity	NPC137718
0.5814	Remote Similarity	NPC473089
0.5802	Remote Similarity	NPC479043
0.5769	Remote Similarity	NPC483886
0.5765	Remote Similarity	NPC483889
0.5667	Remote Similarity	NPC479046
0.5658	Remote Similarity	NPC473081
0.5641	Remote Similarity	NPC483862
0.5625	Remote Similarity	NPC147217
0.5584	Remote Similarity	NPC475429
0.5584	Remote Similarity	NPC211137
0.5581	Remote Similarity	NPC488899
0.5568	Remote Similarity	NPC483864
0.5568	Remote Similarity	NPC127026
0.5568	Remote Similarity	NPC483890
0.5517	Remote Similarity	NPC483881
0.55	Remote Similarity	NPC147880
0.5484	Remote Similarity	NPC488902
0.5484	Remote Similarity	NPC488903
0.5455	Remote Similarity	NPC270498
0.5432	Remote Similarity	NPC148062
0.5294	Remote Similarity	NPC36021
0.5287	Remote Similarity	NPC88593
0.5281	Remote Similarity	NPC6576
0.5256	Remote Similarity	NPC195647
0.525	Remote Similarity	NPC90614
0.5233	Remote Similarity	NPC481068
0.5227	Remote Similarity	NPC488900
0.5185	Remote Similarity	NPC281717
0.5181	Remote Similarity	NPC473758
0.5161	Remote Similarity	NPC483885
0.5122	Remote Similarity	NPC90257
0.5122	Remote Similarity	NPC69357
0.5114	Remote Similarity	NPC14499
0.5114	Remote Similarity	NPC603877
0.5063	Remote Similarity	NPC200592
0.5063	Remote Similarity	NPC610542
0.506	Remote Similarity	NPC139067
0.5056	Remote Similarity	NPC481069
0.5054	Remote Similarity	NPC30171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3957
0.1-0.2	5081
0.2-0.3	109
0.3-0.4	3
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