NPASS Compound

Natural Product: NPC40800

Natural Product ID	NPC40800
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RMBWMWQXPGWZJZ-GSVZXUNASA-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

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 55 58 0 0 0 0 0 0 0 0999 V2000 9.7795 1.3526 -0.8098 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8143 1.0927 -1.7918 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5153 0.8102 -1.4178 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1830 0.7866 -0.0956 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8872 0.5072 0.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9193 0.2490 -0.5843 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2467 0.2709 -1.9202 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5311 0.5474 -2.3606 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5576 -0.0469 -0.1777 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1671 -0.0841 1.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8501 -0.3732 1.4614 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4213 -0.4246 2.6400 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9670 -0.6165 0.4302 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4008 -0.5694 -0.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4935 -0.8185 -1.9238 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8157 -1.1079 -1.6546 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2742 -1.1613 -0.3513 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3609 -0.9121 0.6510 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8116 -0.9625 1.9848 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5668 -1.4443 -0.0134 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6124 -0.5437 0.1522 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6590 -0.8296 -0.8979 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0545 -0.7300 -0.4096 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2828 0.1947 0.7268 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1074 0.4403 1.6051 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4557 0.6751 3.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4216 1.6774 3.0898 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1441 -0.5491 1.4366 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7510 1.4153 0.2016 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4899 -2.0107 -0.0111 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5142 0.0074 -2.0046 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7506 -1.3617 -2.6504 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6452 -0.2933 -1.1177 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7238 1.6687 -1.3131 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9256 0.4260 -0.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4259 2.1524 -0.0988 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9217 0.9858 0.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6731 0.4995 1.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5087 0.0720 -2.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7429 0.5543 -3.4091 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8352 0.1013 1.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 -0.7763 -2.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1261 -0.1020 2.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2253 0.4793 -0.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5147 -1.8752 -1.3007 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7181 -0.4748 -1.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1226 -0.1650 1.3886 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6190 1.3927 1.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8757 -0.2189 3.5423 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5608 1.0713 3.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0724 2.5491 2.7975 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1912 1.2509 -0.6700 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6152 -2.0598 0.9722 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5149 -0.4667 -2.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7609 -2.2520 -3.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 6 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 16 32 1 0 14 33 1 0 8 3 1 0 33 9 1 0 18 13 1 0 28 21 1 0 1 34 1 0 1 35 1 0 1 36 1 0 4 37 1 0 5 38 1 0 7 39 1 0 8 40 1 0 10 41 1 0 15 42 1 0 19 43 1 0 21 44 1 6 22 45 1 6 23 46 1 6 24 47 1 1 25 48 1 6 26 49 1 0 26 50 1 0 27 51 1 0 29 52 1 0 30 53 1 0 31 54 1 0 32 55 1 0 M END

Standard InCHIKey	RMBWMWQXPGWZJZ-GSVZXUNASA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-10-4-2-9(3-5-10)13-6-11(24)16-14(31-13)7-12(25)21(18(16)27)33-22-20(29)19(28)17(26)15(8-23)32-22/h2-7,15,17,19-20,22-23,25-29H,8H2,1H3/t15-,17-,19+,20-,22+/m1/s1
SMILES	COc1ccc(cc1)c1cc(=O)c2c(cc(c(c2O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)o1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.12	Volume:	430.443 ? Van der Waals volume.
Dense:	1.074	LogP:	1.435 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.839 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.191 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	179.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.302	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.877	Fsp³:	0.318
MCE-18:	86.966 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.632	Fluc inhibitor:	0.381 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.958 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.873 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.116	Promiscuous compounds:	0.558

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.169	MDCK Permeability:	-5.278
Pgp-inhibitor:	0.0	Pgp-substrate:	0.251
PAMPA:	0.937 ? 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):	0.469
20% Bioavailability (F20%):	0.507	30% Bioavailability (F30%):	0.979
50% Bioavailability (F50%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.218
Plasma Protein Binding (PPB):	88.162%	Volume Distribution (VD):	-0.105
Fu:	10.696% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.548
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.104	CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.546	CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.583 ? 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):

2.646

Half-life (T1/2):

2.898

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.113
Human Hepatotoxicity (H-HT):	0.561	Drug-induced Liver Injury (DILI):	0.972
AMES Toxicity:	0.864	Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.088	Skin Sensitization:	0.986
Carcinogencity:	0.416	Eye Corrosion:	0.0
Eye Irritation:	0.544	Respiratory Toxicity:	0.03
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.779
Hematotoxicity:	0.287	Drug-induced Nephrotoxicity:	0.363
Genotoxicity:	0.824	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.191	Hek293 Cytotoxicity:	0.343
BCF:	0.351 ? 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:	3.12 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.527 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.715 ? 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
NPO24507	Kalmia angustifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23797	Skimmia reevesiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24507	Kalmia angustifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23797	Skimmia reevesiana	Species	Rutaceae	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 NPC40800 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	18548
0.1-0.2	26732
0.2-0.3	3048
0.3-0.4	1036
0.4-0.5	346
0.5-0.6	104
0.6-0.7	33
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
0.7838	Intermediate Similarity	NPC186807
0.7808	Intermediate Similarity	NPC58053
0.7467	Intermediate Similarity	NPC95090
0.7467	Intermediate Similarity	NPC27408
0.7333	Intermediate Similarity	NPC143851
0.6875	Remote Similarity	NPC605067
0.6795	Remote Similarity	NPC93337
0.675	Remote Similarity	NPC609451
0.6709	Remote Similarity	NPC105025
0.6667	Remote Similarity	NPC22832
0.6585	Remote Similarity	NPC88023
0.6585	Remote Similarity	NPC309025
0.6567	Remote Similarity	NPC156222
0.6543	Remote Similarity	NPC191306
0.65	Remote Similarity	NPC45638
0.6471	Remote Similarity	NPC603300
0.6463	Remote Similarity	NPC243930
0.642	Remote Similarity	NPC201292
0.6386	Remote Similarity	NPC602805
0.6386	Remote Similarity	NPC607707
0.6296	Remote Similarity	NPC488080
0.6296	Remote Similarity	NPC169977
0.625	Remote Similarity	NPC39360
0.625	Remote Similarity	NPC29763
0.625	Remote Similarity	NPC210003
0.622	Remote Similarity	NPC42773
0.622	Remote Similarity	NPC472459
0.622	Remote Similarity	NPC45522
0.619	Remote Similarity	NPC311830
0.6173	Remote Similarity	NPC259152
0.6098	Remote Similarity	NPC181712
0.6098	Remote Similarity	NPC610763
0.6071	Remote Similarity	NPC101026
0.6071	Remote Similarity	NPC488077
0.6071	Remote Similarity	NPC601710
0.6049	Remote Similarity	NPC45618
0.6047	Remote Similarity	NPC211594
0.6026	Remote Similarity	NPC183036
0.5976	Remote Similarity	NPC146792
0.5976	Remote Similarity	NPC189142
0.5976	Remote Similarity	NPC77660
0.5889	Remote Similarity	NPC204693
0.5882	Remote Similarity	NPC601144
0.5854	Remote Similarity	NPC261866
0.5854	Remote Similarity	NPC83283
0.5844	Remote Similarity	NPC470402
0.5833	Remote Similarity	NPC182045
0.5783	Remote Similarity	NPC64305
0.5783	Remote Similarity	NPC168822
0.5745	Remote Similarity	NPC475382
0.5714	Remote Similarity	NPC58716
0.5699	Remote Similarity	NPC124155
0.5699	Remote Similarity	NPC483707
0.5698	Remote Similarity	NPC284960
0.5698	Remote Similarity	NPC120099
0.5698	Remote Similarity	NPC80188
0.5698	Remote Similarity	NPC486578
0.5698	Remote Similarity	NPC609478
0.5663	Remote Similarity	NPC110349
0.5652	Remote Similarity	NPC472992
0.5647	Remote Similarity	NPC222936
0.5647	Remote Similarity	NPC475942
0.5604	Remote Similarity	NPC22062
0.5604	Remote Similarity	NPC473634
0.5604	Remote Similarity	NPC138811
0.5579	Remote Similarity	NPC256760
0.5517	Remote Similarity	NPC21666
0.5493	Remote Similarity	NPC293183
0.5488	Remote Similarity	NPC34287
0.5484	Remote Similarity	NPC488073
0.5479	Remote Similarity	NPC256283
0.5476	Remote Similarity	NPC289667
0.5465	Remote Similarity	NPC21100
0.5455	Remote Similarity	NPC220169
0.5417	Remote Similarity	NPC241498
0.5405	Remote Similarity	NPC255350
0.5402	Remote Similarity	NPC60735
0.5402	Remote Similarity	NPC26230
0.5402	Remote Similarity	NPC285197
0.5376	Remote Similarity	NPC257566
0.5368	Remote Similarity	NPC473623
0.5349	Remote Similarity	NPC602537
0.5342	Remote Similarity	NPC145379
0.5341	Remote Similarity	NPC148710
0.5333	Remote Similarity	NPC172807
0.5319	Remote Similarity	NPC46202
0.5312	Remote Similarity	NPC472991
0.5312	Remote Similarity	NPC488089
0.5294	Remote Similarity	NPC311850
0.5287	Remote Similarity	NPC27942
0.5287	Remote Similarity	NPC117260
0.5275	Remote Similarity	NPC472607
0.5243	Remote Similarity	NPC488083
0.5222	Remote Similarity	NPC203050
0.5222	Remote Similarity	NPC225434
0.5222	Remote Similarity	NPC601586
0.5213	Remote Similarity	NPC131745
0.5176	Remote Similarity	NPC45165
0.5176	Remote Similarity	NPC135345
0.5176	Remote Similarity	NPC331652
0.5172	Remote Similarity	NPC305811
0.5172	Remote Similarity	NPC24043
0.5172	Remote Similarity	NPC84362
0.5172	Remote Similarity	NPC73511
0.5169	Remote Similarity	NPC606560
0.5165	Remote Similarity	NPC4390
0.5143	Remote Similarity	NPC68592
0.5135	Remote Similarity	NPC100887
0.5135	Remote Similarity	NPC184136
0.5135	Remote Similarity	NPC231772
0.5116	Remote Similarity	NPC77672
0.5116	Remote Similarity	NPC133671
0.5116	Remote Similarity	NPC135391
0.5116	Remote Similarity	NPC78263
0.5116	Remote Similarity	NPC250069
0.5114	Remote Similarity	NPC325555
0.5114	Remote Similarity	NPC226304
0.5109	Remote Similarity	NPC8856
0.5109	Remote Similarity	NPC254540
0.5106	Remote Similarity	NPC607513
0.5102	Remote Similarity	NPC477629
0.5096	Remote Similarity	NPC106700
0.5057	Remote Similarity	NPC145038
0.5057	Remote Similarity	NPC56077
0.5057	Remote Similarity	NPC281131
0.5057	Remote Similarity	NPC258035
0.5057	Remote Similarity	NPC253662
0.5057	Remote Similarity	NPC156457
0.5057	Remote Similarity	NPC179950
0.5057	Remote Similarity	NPC277205
0.5057	Remote Similarity	NPC37919
0.5057	Remote Similarity	NPC323593
0.5057	Remote Similarity	NPC88789
0.5057	Remote Similarity	NPC203500
0.5057	Remote Similarity	NPC491374
0.5057	Remote Similarity	NPC603782
0.5056	Remote Similarity	NPC479401
0.5056	Remote Similarity	NPC488071
0.5055	Remote Similarity	NPC488072
0.5054	Remote Similarity	NPC295613
0.5054	Remote Similarity	NPC473657
0.5052	Remote Similarity	NPC209296

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC40800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4747
0.1-0.2	4280
0.2-0.3	105
0.3-0.4	12
0.4-0.5	4
0.5-0.6	2
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
0.5405	Remote Similarity	NPD2801	Pre-clinical
0.5052	Remote Similarity	NPD7054	Phase 4

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