NPASS Compound

Natural Product: NPC201682

Natural Product ID	NPC201682
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MXEMKMNFLXVQBW-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	619168
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 80 84 0 0 0 0 0 0 0 0999 V2000 -4.0621 0.8455 2.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2298 -0.2077 1.6663 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0033 -1.3423 2.3393 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1486 0.3867 0.6359 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0825 -0.2850 -0.6823 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6509 -0.3157 -1.2532 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2256 1.0308 -1.6651 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8831 1.5194 -1.1463 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8310 0.4810 -1.2915 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5712 0.4181 -2.8121 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3581 -0.8031 -0.7639 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4771 -1.7668 -0.7299 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9409 -1.6977 -1.1482 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4625 -0.2939 -1.3114 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8642 -0.2029 -0.8295 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6087 -1.3990 -1.4213 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6507 0.9793 -1.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1364 0.6192 -1.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4663 0.3636 0.2723 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3408 0.1049 1.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8311 -1.0060 2.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2381 1.3037 2.1607 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0265 -0.2586 0.6440 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9667 0.5483 1.3584 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6037 0.4805 0.7864 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4946 0.7136 -0.6768 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9250 2.1310 -0.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7776 -0.9982 -0.2759 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9265 -0.6771 1.1557 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8136 -1.2407 -2.4256 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6034 -0.7957 -3.5675 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1878 -2.5626 -2.2700 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2604 0.4847 3.4474 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9976 1.0734 3.2625 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6196 1.7381 2.2322 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4184 -1.6291 3.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9563 -0.8940 2.7257 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1883 -2.1533 1.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9375 1.4764 0.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2011 0.3366 0.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5198 -1.2897 -0.6801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6525 0.3471 -1.4166 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3310 1.1220 -2.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9601 1.8006 -1.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6683 2.3520 -1.8876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9953 1.9392 -0.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2085 1.2150 -3.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4379 0.7859 -3.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3054 -0.5727 -3.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8221 -2.7455 -0.3510 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4714 -2.2209 -0.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9930 -2.2841 -2.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5391 -0.1338 -2.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5250 -1.6446 -0.8391 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8496 -1.1465 -2.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0420 -2.3202 -1.4758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5469 1.1439 -2.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5676 1.8899 -0.7217 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6567 1.5507 -1.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4781 -0.1584 -1.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0783 1.2476 0.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2554 -0.4521 0.2846 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9422 -1.4576 2.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3831 -1.7417 1.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5495 -0.5988 2.8804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2715 1.3337 2.6277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1528 2.2529 1.6300 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5641 1.1262 2.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8058 -1.3339 0.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2376 1.5958 1.5241 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9101 0.1072 2.4011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1270 -0.4433 1.1663 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0168 1.3063 1.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5069 2.2553 -1.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0625 2.8446 -1.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4166 2.5944 -0.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9546 -2.1085 -0.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6008 -1.5523 1.7663 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1778 0.1258 1.4225 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8772 -3.2367 -2.9461 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 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 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 11 28 1 0 28 29 1 0 6 30 1 0 30 31 2 0 30 32 1 0 29 2 1 0 28 6 1 0 26 9 1 0 26 14 1 0 23 15 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 10 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 16 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 29 78 1 0 29 79 1 0 32 80 1 0 M END

Standard InCHIKey	MXEMKMNFLXVQBW-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-25(2)15-17-30(24(31)32)18-16-28(6)20(21(30)19-25)9-10-23-27(5)13-8-12-26(3,4)22(27)11-14-29(23,28)7/h9,21-23H,8,10-19H2,1-7H3,(H,31,32)
SMILES	CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCCC(C)(C)C5CCC34C)C2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	496.961 ? Van der Waals volume.
Dense:	0.886	LogP:	5.108 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.131 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.856 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.417	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.495	Fsp³:	0.9
MCE-18:	102.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.374	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.052 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.611	Promiscuous compounds:	0.008

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04	MDCK Permeability:	-4.843
Pgp-inhibitor:	0.001	Pgp-substrate:	0.0
PAMPA:	0.227 ? 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%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.166

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993	MRP1:	1.0
Plasma Protein Binding (PPB):	97.545%	Volume Distribution (VD):	0.078
Fu:	3.117% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.018
OATP1B3 inhibitor:	0.783	BCRP inhibitor:	0.0
BSEP inhibitor:	0.892

ADMET: Metabolism

CYP1A2-inhibitor:	0.019	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.047	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.191
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.225
HLM stability:	0.997 ? 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):

3.332

Half-life (T1/2):

0.926

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.327
Human Hepatotoxicity (H-HT):	0.434	Drug-induced Liver Injury (DILI):	0.111
AMES Toxicity:	0.023	Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.749	Skin Sensitization:	0.41
Carcinogencity:	0.171	Eye Corrosion:	0.042
Eye Irritation:	0.531	Respiratory Toxicity:	0.835
Drug-induced Neurotoxicity:	0.182	Ototoxicity:	0.904
Hematotoxicity:	0.223	Drug-induced Nephrotoxicity:	0.14
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.144	Hek293 Cytotoxicity:	0.122
BCF:	1.997 ? 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:	5.057 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.382 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.262 ? 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
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	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

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

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 NPC201682 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	31203
0.1-0.2	15665
0.2-0.3	2329
0.3-0.4	378
0.4-0.5	183
0.5-0.6	61
0.6-0.7	23
0.7-0.8	0
0.8-0.85	0
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	NPC604575
0.7097	Intermediate Similarity	NPC480946
0.7097	Intermediate Similarity	NPC130577
0.7097	Intermediate Similarity	NPC142415
0.7097	Intermediate Similarity	NPC102683
0.6984	Remote Similarity	NPC270768
0.6984	Remote Similarity	NPC59263
0.6984	Remote Similarity	NPC210106
0.6875	Remote Similarity	NPC158141
0.6774	Remote Similarity	NPC280654
0.6769	Remote Similarity	NPC200752
0.6769	Remote Similarity	NPC120840
0.6769	Remote Similarity	NPC298554
0.6719	Remote Similarity	NPC84319
0.6719	Remote Similarity	NPC52021
0.6719	Remote Similarity	NPC599947
0.6615	Remote Similarity	NPC231063
0.6615	Remote Similarity	NPC282395
0.6615	Remote Similarity	NPC110308
0.6462	Remote Similarity	NPC282616
0.6462	Remote Similarity	NPC275809
0.6462	Remote Similarity	NPC37038
0.6462	Remote Similarity	NPC156981
0.6377	Remote Similarity	NPC96580
0.6364	Remote Similarity	NPC106112
0.6364	Remote Similarity	NPC261935
0.6364	Remote Similarity	NPC481360
0.6232	Remote Similarity	NPC296164
0.597	Remote Similarity	NPC182797
0.597	Remote Similarity	NPC121798
0.597	Remote Similarity	NPC234346
0.597	Remote Similarity	NPC52169
0.597	Remote Similarity	NPC488562
0.5942	Remote Similarity	NPC474963
0.5821	Remote Similarity	NPC198664
0.5735	Remote Similarity	NPC307282
0.5735	Remote Similarity	NPC64872
0.5735	Remote Similarity	NPC25906
0.5714	Remote Similarity	NPC204407
0.5676	Remote Similarity	NPC481362
0.5652	Remote Similarity	NPC130278
0.5652	Remote Similarity	NPC472149
0.5652	Remote Similarity	NPC609452
0.5641	Remote Similarity	NPC283849
0.5641	Remote Similarity	NPC28198
0.5641	Remote Similarity	NPC476123
0.5641	Remote Similarity	NPC606107
0.5616	Remote Similarity	NPC474727
0.5571	Remote Similarity	NPC291028
0.55	Remote Similarity	NPC286347
0.5441	Remote Similarity	NPC267691
0.5432	Remote Similarity	NPC100383
0.5429	Remote Similarity	NPC88116
0.5417	Remote Similarity	NPC130520
0.5366	Remote Similarity	NPC43353
0.5362	Remote Similarity	NPC474806
0.5362	Remote Similarity	NPC133579
0.5352	Remote Similarity	NPC228784
0.5352	Remote Similarity	NPC324341
0.5352	Remote Similarity	NPC601810
0.5301	Remote Similarity	NPC294112
0.5301	Remote Similarity	NPC284807
0.5301	Remote Similarity	NPC473538
0.5286	Remote Similarity	NPC32118
0.5278	Remote Similarity	NPC201657
0.5238	Remote Similarity	NPC191410
0.5217	Remote Similarity	NPC274050
0.5217	Remote Similarity	NPC162632
0.5211	Remote Similarity	NPC271614
0.5176	Remote Similarity	NPC475472
0.5176	Remote Similarity	NPC475611
0.5143	Remote Similarity	NPC187722
0.5139	Remote Similarity	NPC145667
0.5139	Remote Similarity	NPC477288
0.5135	Remote Similarity	NPC324063
0.5135	Remote Similarity	NPC222047
0.5135	Remote Similarity	NPC488521
0.5116	Remote Similarity	NPC22676
0.5116	Remote Similarity	NPC270667
0.5116	Remote Similarity	NPC164194
0.507	Remote Similarity	NPC229281
0.507	Remote Similarity	NPC51700
0.507	Remote Similarity	NPC88716
0.507	Remote Similarity	NPC306541
0.507	Remote Similarity	NPC68160
0.507	Remote Similarity	NPC606443
0.5065	Remote Similarity	NPC188833
0.5057	Remote Similarity	NPC198621
0.5057	Remote Similarity	NPC216940

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC201682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7185
0.1-0.2	1932
0.2-0.3	25
0.3-0.4	7
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