NPASS Compound

Natural Product: NPC483765

Natural Product ID	NPC483765
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OIVQBYYDTZPGQC-PUSCWQRGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 89 94 0 0 0 0 0 0 0 0999 V2000 2.5415 -1.3874 -2.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6816 -1.1050 -1.3949 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5366 -0.5997 -0.2515 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8761 0.5383 0.3855 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3427 0.2628 0.5251 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2239 -0.0746 -0.7995 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8122 -0.0984 -1.7694 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8728 -1.3292 -0.9325 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0763 -1.3777 -1.6458 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9915 -1.5069 -3.0464 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8629 -1.5818 -3.5876 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1381 -1.5477 -3.7836 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1353 -1.6717 -5.1678 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2928 -1.7113 -5.9155 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4790 -1.6201 -5.2083 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5137 -1.4973 -3.8446 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3303 -1.4591 -3.1048 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3483 -1.3438 -1.8189 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2710 -1.2982 -1.0241 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4701 -1.1701 0.4135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7345 -0.7835 0.8686 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0466 -0.6939 2.2051 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1152 -0.9849 3.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8634 -1.3688 2.7532 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5615 -1.4555 1.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9144 -1.6666 3.7125 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4041 -0.9012 4.5354 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6917 -0.5045 4.9595 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6833 -1.6537 -5.9040 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9075 -1.7565 -5.7924 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1591 1.5704 0.8575 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6820 1.9202 2.0645 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7503 1.0849 2.9728 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1543 3.3139 2.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0585 4.1788 1.2305 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4883 5.5607 1.2880 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0562 6.1495 2.3948 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4530 7.4908 2.3991 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2899 8.2696 1.2971 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7223 7.6931 0.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3294 6.3777 0.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6625 9.6149 1.2299 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9225 1.6665 -0.4358 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9429 -1.6830 0.4748 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2326 -2.1964 0.5851 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9999 -1.5316 -0.0779 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5572 -3.3344 1.3705 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7025 -3.8878 1.4753 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9096 -3.5257 0.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0812 -3.7375 1.5911 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3419 -3.5516 1.0928 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5317 -3.1413 -0.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4322 -2.9247 -0.9751 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1385 -3.1218 -0.4485 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8144 -2.9625 -0.6659 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4518 -0.7332 -2.6191 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0071 -1.1329 -3.5603 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8072 -2.4575 -2.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1584 -2.0385 -1.1033 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4651 -0.2039 -0.7579 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1686 0.8471 1.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2620 -0.4517 1.3287 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9180 0.7154 -1.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3071 -1.8074 -6.9897 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4356 -1.4270 -3.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4824 -0.5495 0.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0314 -0.3922 2.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5895 -1.7845 1.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4373 -2.5459 3.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0462 0.4057 4.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6947 -0.2389 6.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4267 -1.3286 4.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4970 -2.0222 -5.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6294 -2.6586 -6.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5766 3.6531 3.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6215 3.8381 0.2739 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2026 5.5523 3.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8921 7.9032 3.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5890 8.3177 -0.7076 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8896 5.9895 -0.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0191 10.2312 0.7517 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4208 2.4077 -0.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6714 -3.7554 1.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7066 -4.7865 2.1821 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0149 -4.0666 2.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2101 -3.7335 1.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5718 -2.6005 -1.9981 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3730 -2.9940 -1.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3337 -2.0966 -0.5305 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 0 6 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 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 27 28 1 0 15 29 1 0 13 30 1 0 5 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 4 43 1 0 3 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 52 55 1 0 7 2 1 0 19 9 2 0 25 20 1 0 41 36 1 0 54 49 1 0 17 12 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 1 3 60 1 6 4 61 1 1 5 62 1 1 6 63 1 6 14 64 1 0 16 65 1 0 21 66 1 0 22 67 1 0 25 68 1 0 26 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 30 74 1 0 34 75 1 0 35 76 1 0 37 77 1 0 38 78 1 0 40 79 1 0 41 80 1 0 42 81 1 0 43 82 1 0 47 83 1 0 48 84 1 0 50 85 1 0 51 86 1 0 53 87 1 0 54 88 1 0 55 89 1 0 M END

Standard InCHIKey	OIVQBYYDTZPGQC-PUSCWQRGSA-N
Standard InCHI	InChI=1S/C40H34O15/c1-20-36(53-31(46)15-7-21-3-10-24(41)11-4-21)35(49)39(54-32(47)16-8-22-5-12-25(42)13-6-22)40(51-20)55-38-34(48)33-28(45)18-26(43)19-30(33)52-37(38)23-9-14-29(50-2)27(44)17-23/h3-20,35-36,39-45,49H,1-2H3/b15-7-,16-8+/t20-,35+,36-,39+,40-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)OC)O)O)OC(=O)/C=C/c1ccc(cc1)O)O)OC(=O)/C=Cc1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	754.19	Volume:	733.454 ? Van der Waals volume.
Dense:	1.028	LogP:	3.678 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.85 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.463 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	40.0
TPSA:	231.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.084	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.599	Fsp³:	0.175
MCE-18:	125.298 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.887 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.687 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.331	Promiscuous compounds:	0.733

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.021	MDCK Permeability:	-5.135
Pgp-inhibitor:	0.46	Pgp-substrate:	0.024
PAMPA:	0.806 ? 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):	0.002
20% Bioavailability (F20%):	0.926	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.005
Plasma Protein Binding (PPB):	95.413%	Volume Distribution (VD):	-0.176
Fu:	4.626% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.457
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.038	CYP2D6-substrate:	0.341
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.898 ? 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):

2.63

Half-life (T1/2):

2.975

ADMET: Toxicity

hERG Blockers:	0.321	hERG Blockers (10um):	0.743
Human Hepatotoxicity (H-HT):	0.667	Drug-induced Liver Injury (DILI):	0.465
AMES Toxicity:	0.48	Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.867	Skin Sensitization:	1.0
Carcinogencity:	0.027	Eye Corrosion:	0.0
Eye Irritation:	0.924	Respiratory Toxicity:	0.29
Drug-induced Neurotoxicity:	0.108	Ototoxicity:	0.216
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.101
Genotoxicity:	0.947	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.966	Hek293 Cytotoxicity:	0.991
BCF:	0.922 ? 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:	4.405 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.279 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.106 ? 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
NPO40193	Machilus litseifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30668111]

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
IC50	1
Ratio IC50	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	28200.0	nM	PMID[30668111]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	8.0	n.a.	PMID[30668111]

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 NPC483765 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	12158
0.1-0.2	32906
0.2-0.3	3954
0.3-0.4	533
0.4-0.5	209
0.5-0.6	57
0.6-0.7	22
0.7-0.8	0
0.8-0.85	0
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8989	High Similarity	NPC483767
0.8989	High Similarity	NPC483769
0.8989	High Similarity	NPC483768
0.8989	High Similarity	NPC483766
0.8864	High Similarity	NPC221288
0.8864	High Similarity	NPC194836
0.8864	High Similarity	NPC91493
0.8864	High Similarity	NPC605081
0.7113	Intermediate Similarity	NPC101399
0.7113	Intermediate Similarity	NPC217822
0.7113	Intermediate Similarity	NPC11847
0.7113	Intermediate Similarity	NPC198938
0.701	Intermediate Similarity	NPC104883
0.701	Intermediate Similarity	NPC488679
0.6923	Remote Similarity	NPC259957
0.6923	Remote Similarity	NPC470718
0.6733	Remote Similarity	NPC218161
0.6667	Remote Similarity	NPC30011
0.6514	Remote Similarity	NPC162394
0.6491	Remote Similarity	NPC231787
0.6415	Remote Similarity	NPC470712
0.6383	Remote Similarity	NPC484158
0.6275	Remote Similarity	NPC205824
0.6239	Remote Similarity	NPC72554
0.6126	Remote Similarity	NPC470713
0.6071	Remote Similarity	NPC156785
0.6038	Remote Similarity	NPC478277
0.6038	Remote Similarity	NPC96605
0.6038	Remote Similarity	NPC280642
0.6038	Remote Similarity	NPC478276
0.6038	Remote Similarity	NPC478275
0.6038	Remote Similarity	NPC92815
0.6036	Remote Similarity	NPC474093
0.6036	Remote Similarity	NPC104910
0.6033	Remote Similarity	NPC97817
0.6	Remote Similarity	NPC249560
0.5943	Remote Similarity	NPC223426
0.5932	Remote Similarity	NPC275977
0.5872	Remote Similarity	NPC477895
0.5826	Remote Similarity	NPC241781
0.5818	Remote Similarity	NPC217520
0.5773	Remote Similarity	NPC219904
0.5769	Remote Similarity	NPC477628
0.5755	Remote Similarity	NPC85751
0.5755	Remote Similarity	NPC19240
0.567	Remote Similarity	NPC216496
0.563	Remote Similarity	NPC21359
0.563	Remote Similarity	NPC460984
0.5612	Remote Similarity	NPC48093
0.5556	Remote Similarity	NPC260504
0.5556	Remote Similarity	NPC120099
0.5556	Remote Similarity	NPC89809
0.5556	Remote Similarity	NPC224530
0.5546	Remote Similarity	NPC25946
0.5528	Remote Similarity	NPC487502
0.5521	Remote Similarity	NPC104677
0.5517	Remote Similarity	NPC474522
0.55	Remote Similarity	NPC209023
0.5465	Remote Similarity	NPC82325
0.5455	Remote Similarity	NPC159579
0.5455	Remote Similarity	NPC81042
0.5398	Remote Similarity	NPC470715
0.5398	Remote Similarity	NPC164704
0.5385	Remote Similarity	NPC33083
0.5385	Remote Similarity	NPC470719
0.5315	Remote Similarity	NPC214621
0.5315	Remote Similarity	NPC34267
0.5312	Remote Similarity	NPC475179
0.5312	Remote Similarity	NPC487501
0.5304	Remote Similarity	NPC139571
0.5285	Remote Similarity	NPC473554
0.5283	Remote Similarity	NPC35167
0.5278	Remote Similarity	NPC473327
0.5254	Remote Similarity	NPC470717
0.5248	Remote Similarity	NPC85707
0.5248	Remote Similarity	NPC609478
0.5229	Remote Similarity	NPC472991
0.521	Remote Similarity	NPC470720
0.5149	Remote Similarity	NPC60735
0.5149	Remote Similarity	NPC175107
0.5149	Remote Similarity	NPC129217
0.5149	Remote Similarity	NPC26230
0.5122	Remote Similarity	NPC480470
0.5116	Remote Similarity	NPC487500
0.51	Remote Similarity	NPC52550
0.5096	Remote Similarity	NPC95866
0.5093	Remote Similarity	NPC253521
0.5093	Remote Similarity	NPC470125
0.5093	Remote Similarity	NPC472992
0.5093	Remote Similarity	NPC113836
0.5085	Remote Similarity	NPC295625
0.5045	Remote Similarity	NPC89127
0.5043	Remote Similarity	NPC173837

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3961
0.1-0.2	5125
0.2-0.3	55
0.3-0.4	8
0.4-0.5	1
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