NPASS Compound

Natural Product: NPC472571

Natural Product ID	NPC472571
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RKQBXPZSTLHXPR-XFOFPURASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3577215
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 86 90 0 0 0 0 0 0 0 0999 V2000 -5.4788 -0.1315 3.3222 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2120 -0.5989 1.9410 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1777 -0.5758 1.1350 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9585 -1.0377 1.5638 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7517 -1.4726 0.2380 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2944 -2.8823 0.2639 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2476 -3.2495 -0.7063 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2945 -2.1994 -1.1399 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1426 -2.6578 -1.1238 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6520 -1.7264 -2.2242 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6633 -0.3083 -1.7998 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5475 0.1670 -1.0303 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3851 -0.8858 -0.4019 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8229 -0.4885 -0.4357 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9984 0.7565 0.2072 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5490 1.8543 -0.4435 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9022 1.7568 -1.6300 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7025 3.1248 0.3039 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9459 -1.0027 1.0420 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0165 1.0140 -0.0055 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0668 2.3716 0.0096 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6448 2.9926 -0.8939 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5499 3.0984 1.1334 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1986 2.4310 2.1518 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7811 3.1181 3.2128 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7270 4.4883 3.2776 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0809 5.1557 2.2635 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5022 4.4732 1.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8782 0.0068 -1.1004 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8266 0.8895 -1.5728 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6139 1.4494 -2.6769 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0461 1.1766 -0.8255 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2988 0.6058 0.3346 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4826 0.8543 1.1085 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4709 1.7141 0.7138 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6054 1.9245 1.5019 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7372 1.2579 2.6976 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7583 0.3862 3.1205 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6637 0.2083 2.3200 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4695 -1.9187 -3.2151 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6126 -1.9015 -2.4833 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2071 -3.2110 -3.9483 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4924 -0.8242 -4.2636 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7902 -2.4892 0.0554 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9127 -3.9339 -1.9106 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4698 -4.2722 -0.1080 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7847 -0.9948 3.9403 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3251 0.5909 3.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5401 0.3134 3.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7251 -1.3690 -0.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0498 -3.2100 1.3222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2125 -3.5218 0.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2268 -3.6958 -1.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6286 -2.0196 -2.5971 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7155 0.3054 -2.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1267 0.8797 -1.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1365 -0.3704 -1.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7517 3.4491 0.7961 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4952 3.0185 1.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0405 3.9445 -0.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0900 -0.5639 1.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6012 -0.3319 1.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0016 -1.9989 1.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2749 1.3594 2.1582 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2911 2.5969 4.0142 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1921 4.9976 4.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0461 6.2341 2.3270 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0121 5.0524 0.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7522 1.8661 -1.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5484 -0.0953 0.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4323 2.2616 -0.2022 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3848 2.5976 1.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6231 1.4155 3.3223 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8385 -0.1592 4.0708 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8990 -0.4743 2.6544 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7385 -3.2030 -4.9447 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4001 -4.1129 -3.3776 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8898 -3.2160 -4.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5365 -0.5369 -4.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0710 0.0512 -3.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9986 -1.2556 -5.1582 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6698 -2.0544 -0.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9521 -4.2436 -1.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9796 -3.2210 -2.7748 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3651 -4.8388 -2.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0970 -4.9548 0.2030 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 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 13 19 1 0 12 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 11 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 3 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 10 40 1 0 40 41 1 0 40 42 1 0 40 43 1 0 9 44 1 0 7 45 1 0 7 46 1 0 14 5 1 0 13 8 1 0 41 8 1 0 28 23 1 0 39 34 1 0 1 47 1 0 1 48 1 0 1 49 1 0 5 50 1 0 6 51 1 0 6 52 1 0 9 53 1 0 10 54 1 0 11 55 1 0 12 56 1 0 14 57 1 0 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 19 63 1 0 24 64 1 0 25 65 1 0 26 66 1 0 27 67 1 0 28 68 1 0 32 69 1 0 33 70 1 0 35 71 1 0 36 72 1 0 37 73 1 0 38 74 1 0 39 75 1 0 42 76 1 0 42 77 1 0 42 78 1 0 43 79 1 0 43 80 1 0 43 81 1 0 44 82 1 0 45 83 1 0 45 84 1 0 45 85 1 0 46 86 1 0 M END

Standard InCHIKey	RKQBXPZSTLHXPR-XFOFPURASA-N
Standard InCHI	InChI=1S/C35H40O11/c1-20(36)42-24-19-33(5,41)35-28(39)26(32(3,4)46-35)27(44-25(38)18-17-22-13-9-7-10-14-22)30(34(35,6)29(24)43-21(2)37)45-31(40)23-15-11-8-12-16-23/h7-18,24,26-30,39,41H,19H2,1-6H3/b18-17+/t24-,26+,27-,28+,29-,30-,33-,34-,35-/m0/s1
SMILES	CC(=O)OC1CC(C23C(C(C(C(C2(C1OC(=O)C)C)OC(=O)C4=CC=CC=C4)OC(=O)C=CC5=CC=CC=C5)C(O3)(C)C)O)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.26	Volume:	638.825 ? Van der Waals volume.
Dense:	0.996	LogP:	3.738 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.43 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.084 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	31.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.261	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.948	Fsp³:	0.486
MCE-18:	172.5 ? 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:	0.723	Fluc inhibitor:	0.32 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.046 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.639 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.136	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.164	MDCK Permeability:	-4.772
Pgp-inhibitor:	0.988	Pgp-substrate:	0.89
PAMPA:	0.97 ? 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):	0.219
20% Bioavailability (F20%):	0.781	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	1.0
Plasma Protein Binding (PPB):	91.145%	Volume Distribution (VD):	-0.292
Fu:	9.904% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.129
OATP1B3 inhibitor:	0.601	BCRP inhibitor:	0.001
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.704
CYP2C19-inhibitor:	0.05	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.359	CYP2C9-substrate:	0.818
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.75
CYP3A4-inhibitor:	0.055	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

0.825

Half-life (T1/2):

1.53

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.599
Human Hepatotoxicity (H-HT):	0.152	Drug-induced Liver Injury (DILI):	0.51
AMES Toxicity:	0.367	Rat Oral Acute Toxicity:	0.191
Maximum Recommended Daily Dose:	0.337	Skin Sensitization:	0.979
Carcinogencity:	0.131	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.683	Ototoxicity:	0.784
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.305
Genotoxicity:	0.15	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.102	Hek293 Cytotoxicity:	0.713
BCF:	1.003 ? 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:	3.913 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.892 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.276 ? 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
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO15653	Celastrus vulcanicola	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
Ratio IC50	6
Ki	1
Activity	1

Activity Type	# Activity
Individual protein	8

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	87.1	n.a.	PMID[18461966]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	24.1	n.a.	PMID[22194678]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	12.8	n.a.	PMID[22194678]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	20.4	n.a.	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	16.4	n.a.	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	6.0	n.a.	PMID[21155593]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	420.0	nM	PMID[21155593]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	85.1	%	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC472571 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	9851
0.1-0.2	35923
0.2-0.3	3325
0.3-0.4	613
0.4-0.5	96
0.5-0.6	37
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	0

Similarity Score	Similarity Level	Natural Product ID
0.7867	Intermediate Similarity	NPC470159
0.7763	Intermediate Similarity	NPC70403
0.7763	Intermediate Similarity	NPC177940
0.6835	Remote Similarity	NPC488908
0.6835	Remote Similarity	NPC488906
0.6625	Remote Similarity	NPC29704
0.6625	Remote Similarity	NPC470157
0.6582	Remote Similarity	NPC481490
0.6341	Remote Similarity	NPC483878
0.6265	Remote Similarity	NPC605086
0.6104	Remote Similarity	NPC87448
0.6	Remote Similarity	NPC174982
0.5904	Remote Similarity	NPC609221
0.5814	Remote Similarity	NPC125106
0.5814	Remote Similarity	NPC472573
0.5814	Remote Similarity	NPC483860
0.5765	Remote Similarity	NPC603877
0.5747	Remote Similarity	NPC171525
0.5747	Remote Similarity	NPC483859
0.5714	Remote Similarity	NPC470153
0.5714	Remote Similarity	NPC481050
0.5663	Remote Similarity	NPC106895
0.5647	Remote Similarity	NPC488920
0.5568	Remote Similarity	NPC488916
0.5529	Remote Similarity	NPC488907
0.5474	Remote Similarity	NPC294579
0.5474	Remote Similarity	NPC144779
0.5465	Remote Similarity	NPC481487
0.5455	Remote Similarity	NPC483861
0.5412	Remote Similarity	NPC607428
0.5393	Remote Similarity	NPC184817
0.5341	Remote Similarity	NPC25768
0.5341	Remote Similarity	NPC483866
0.5309	Remote Similarity	NPC281717
0.5294	Remote Similarity	NPC214550
0.5281	Remote Similarity	NPC469349
0.5233	Remote Similarity	NPC488909
0.5233	Remote Similarity	NPC473085
0.5233	Remote Similarity	NPC473112
0.5233	Remote Similarity	NPC488905
0.5222	Remote Similarity	NPC188865
0.5181	Remote Similarity	NPC471101
0.5161	Remote Similarity	NPC86800
0.5114	Remote Similarity	NPC488912
0.5114	Remote Similarity	NPC488910
0.5111	Remote Similarity	NPC483865
0.5062	Remote Similarity	NPC118080
0.5056	Remote Similarity	NPC483867
0.5056	Remote Similarity	NPC488917

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3826
0.1-0.2	5183
0.2-0.3	136
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