NPASS Compound

Natural Product: NPC483768

Natural Product ID	NPC483768
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FSJKWOXNSZKWAF-SNEURSICSA-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]

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 88 93 0 0 0 0 0 0 0 0999 V2000 1.3883 -2.9847 1.2710 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1866 -1.4730 0.9471 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6693 -1.3094 -0.4436 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2338 -0.0582 -1.0833 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0953 0.5736 -0.2917 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8165 -0.4068 0.3013 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0789 -1.1580 1.2526 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7770 0.2694 1.1611 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8403 -0.4610 1.6813 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -1.1056 2.9047 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4092 -0.9996 3.4496 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5529 -1.8504 3.4571 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3303 -2.5090 4.6508 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3590 -3.2515 5.1877 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5894 -3.3486 4.5666 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7642 -2.6680 3.3692 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7581 -1.9226 2.8123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9570 -1.3002 1.6930 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0273 -0.5501 1.0815 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4110 0.0853 -0.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7460 1.0900 -0.8010 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1923 1.5727 -2.0169 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3324 1.0563 -2.6364 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0233 0.0397 -2.0122 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5533 -0.4168 -0.8071 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7856 1.5375 -3.8568 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9306 0.9998 -4.4495 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5636 -4.1097 5.1677 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0975 -2.3956 5.2482 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4466 1.5640 -1.1143 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3025 2.9471 -0.8475 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3412 3.1906 0.1729 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8848 3.8670 -1.7363 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9084 5.1522 -1.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3620 5.9171 -0.5455 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2022 7.1680 -0.9019 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6662 8.0757 -0.0069 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6086 7.8128 1.3576 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0693 6.6161 1.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4050 5.6960 0.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0932 8.7627 2.2239 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8544 -0.1847 -2.4247 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0840 -1.4734 -0.4543 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7698 -2.4785 -1.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1076 -3.3559 -1.6909 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2366 -2.5842 -1.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8229 -3.5697 -1.6445 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2643 -3.7181 -1.6412 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8517 -4.7998 -2.3220 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2094 -4.9691 -2.3376 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0365 -4.0897 -1.6908 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5092 -3.0197 -1.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1209 -2.8575 -1.0049 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4281 -4.2851 -1.7210 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6868 -3.2330 2.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0941 -3.5185 0.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4462 -3.1425 1.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 -0.9713 1.6938 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2834 -2.1862 -1.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1167 0.6496 -1.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6138 1.1127 0.5451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3026 -1.1561 -0.3123 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1806 -3.7755 6.1397 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7503 -2.7709 2.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8875 1.5105 -0.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6505 2.3738 -2.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9247 -0.3882 -2.4740 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1319 -1.2307 -0.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7439 -0.0095 -4.9067 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8122 0.9865 -3.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2211 1.6447 -5.3033 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3389 -3.6500 5.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8923 -1.6037 5.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3910 3.4189 -2.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4185 5.7139 -2.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2666 7.4124 -1.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1005 9.0426 -0.3089 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0049 6.3721 2.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8903 4.8164 1.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0701 9.0879 2.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1650 0.5872 -2.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7648 -1.8266 -0.4965 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2233 -4.3308 -2.1884 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2047 -5.4843 -2.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6795 -5.8107 -2.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0921 -2.2905 -0.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7131 -2.0122 -0.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0439 -3.6677 -2.2403 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 23 26 1 0 26 27 1 0 15 28 1 0 13 29 1 0 5 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 38 41 1 0 4 42 1 0 3 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 51 52 1 0 52 53 2 0 51 54 1 0 7 2 1 0 19 9 2 0 25 20 1 0 40 35 1 0 53 48 1 0 17 12 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 1 3 59 1 6 4 60 1 6 5 61 1 1 6 62 1 6 14 63 1 0 16 64 1 0 21 65 1 0 22 66 1 0 24 67 1 0 25 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 29 73 1 0 33 74 1 0 34 75 1 0 36 76 1 0 37 77 1 0 39 78 1 0 40 79 1 0 41 80 1 0 42 81 1 0 46 82 1 0 47 83 1 0 49 84 1 0 50 85 1 0 52 86 1 0 53 87 1 0 54 88 1 0 M END

Standard InCHIKey	FSJKWOXNSZKWAF-SNEURSICSA-N
Standard InCHI	InChI=1S/C40H34O14/c1-21-36(52-31(45)17-7-22-3-11-25(41)12-4-22)35(48)39(53-32(46)18-8-23-5-13-26(42)14-6-23)40(50-21)54-38-34(47)33-29(44)19-27(43)20-30(33)51-37(38)24-9-15-28(49-2)16-10-24/h3-21,35-36,39-44,48H,1-2H3/b17-7+,18-8-/t21-,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(cc1)OC)O)O)OC(=O)/C=Cc1ccc(cc1)O)O)OC(=O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	738.19	Volume:	724.664 ? Van der Waals volume.
Dense:	1.019	LogP:	4.184 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.292 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.632 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	40.0
TPSA:	211.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.094	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.489	Fsp³:	0.175
MCE-18:	122.085 ? 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:	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:	0.902 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.735 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.344	Promiscuous compounds:	0.491

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.935	MDCK Permeability:	-5.082
Pgp-inhibitor:	0.732	Pgp-substrate:	0.016
PAMPA:	0.746 ? 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):	0.012
20% Bioavailability (F20%):	0.92	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.006
Plasma Protein Binding (PPB):	96.885%	Volume Distribution (VD):	-0.066
Fu:	2.91% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.404
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.657
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.062	CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.912 ? 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):

3.608

Half-life (T1/2):

2.137

ADMET: Toxicity

hERG Blockers:	0.412	hERG Blockers (10um):	0.734
Human Hepatotoxicity (H-HT):	0.667	Drug-induced Liver Injury (DILI):	0.818
AMES Toxicity:	0.594	Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.901	Skin Sensitization:	1.0
Carcinogencity:	0.045	Eye Corrosion:	0.0
Eye Irritation:	0.845	Respiratory Toxicity:	0.206
Drug-induced Neurotoxicity:	0.125	Ototoxicity:	0.183
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.15
Genotoxicity:	0.96	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.934	Hek293 Cytotoxicity:	0.992
BCF:	1.053 ? 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:	4.737 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.743 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.548 ? 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	=	10100.0	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 NPC483768 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	11855
0.1-0.2	32988
0.2-0.3	4128
0.3-0.4	565
0.4-0.5	219
0.5-0.6	59
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC483767
1.0	High Similarity	NPC483769
1.0	High Similarity	NPC483766
0.9186	High Similarity	NPC221288
0.9186	High Similarity	NPC194836
0.9186	High Similarity	NPC91493
0.9186	High Similarity	NPC605081
0.8989	High Similarity	NPC483765
0.7368	Intermediate Similarity	NPC101399
0.7368	Intermediate Similarity	NPC217822
0.7368	Intermediate Similarity	NPC11847
0.7368	Intermediate Similarity	NPC198938
0.7263	Intermediate Similarity	NPC104883
0.7263	Intermediate Similarity	NPC488679
0.7191	Intermediate Similarity	NPC259957
0.697	Remote Similarity	NPC218161
0.6961	Remote Similarity	NPC470712
0.6696	Remote Similarity	NPC231787
0.6579	Remote Similarity	NPC30011
0.65	Remote Similarity	NPC205824
0.6481	Remote Similarity	NPC470713
0.6452	Remote Similarity	NPC484158
0.6422	Remote Similarity	NPC162394
0.6355	Remote Similarity	NPC470718
0.625	Remote Similarity	NPC478277
0.625	Remote Similarity	NPC96605
0.625	Remote Similarity	NPC280642
0.625	Remote Similarity	NPC478276
0.625	Remote Similarity	NPC478275
0.625	Remote Similarity	NPC92815
0.6154	Remote Similarity	NPC72554
0.6139	Remote Similarity	NPC477628
0.6091	Remote Similarity	NPC474093
0.6091	Remote Similarity	NPC104910
0.5982	Remote Similarity	NPC156785
0.5962	Remote Similarity	NPC85751
0.5962	Remote Similarity	NPC19240
0.595	Remote Similarity	NPC97817
0.5926	Remote Similarity	NPC477895
0.5917	Remote Similarity	NPC249560
0.5905	Remote Similarity	NPC260504
0.5905	Remote Similarity	NPC89809
0.5895	Remote Similarity	NPC216496
0.5872	Remote Similarity	NPC470715
0.5849	Remote Similarity	NPC223426
0.5847	Remote Similarity	NPC275977
0.5833	Remote Similarity	NPC48093
0.5773	Remote Similarity	NPC224530
0.5745	Remote Similarity	NPC104677
0.5739	Remote Similarity	NPC241781
0.5727	Remote Similarity	NPC217520
0.5727	Remote Similarity	NPC164704
0.5702	Remote Similarity	NPC474522
0.567	Remote Similarity	NPC159579
0.5593	Remote Similarity	NPC25946
0.5505	Remote Similarity	NPC214621
0.5505	Remote Similarity	NPC34267
0.5455	Remote Similarity	NPC85707
0.5447	Remote Similarity	NPC487502
0.5431	Remote Similarity	NPC470717
0.5417	Remote Similarity	NPC21359
0.5417	Remote Similarity	NPC460984
0.5408	Remote Similarity	NPC472459
0.54	Remote Similarity	NPC209023
0.5391	Remote Similarity	NPC295625
0.5385	Remote Similarity	NPC470720
0.5364	Remote Similarity	NPC81042
0.5354	Remote Similarity	NPC475179
0.5354	Remote Similarity	NPC129217
0.5351	Remote Similarity	NPC470716
0.5328	Remote Similarity	NPC473554
0.5308	Remote Similarity	NPC33083
0.5294	Remote Similarity	NPC59951
0.5283	Remote Similarity	NPC470125
0.5278	Remote Similarity	NPC472991
0.5229	Remote Similarity	NPC477629
0.5217	Remote Similarity	NPC139571
0.5196	Remote Similarity	NPC476215
0.5189	Remote Similarity	NPC35167
0.5185	Remote Similarity	NPC139060
0.5182	Remote Similarity	NPC36138
0.514	Remote Similarity	NPC61904
0.514	Remote Similarity	NPC472992
0.5116	Remote Similarity	NPC487501
0.5093	Remote Similarity	NPC297503
0.5091	Remote Similarity	NPC188815
0.5051	Remote Similarity	NPC64305
0.505	Remote Similarity	NPC182121
0.505	Remote Similarity	NPC175107
0.505	Remote Similarity	NPC219904
0.5049	Remote Similarity	NPC170052
0.5049	Remote Similarity	NPC135846
0.5042	Remote Similarity	NPC470719

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3784
0.1-0.2	5286
0.2-0.3	70
0.3-0.4	9
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