NPASS Compound

Natural Product: NPC279268

Natural Product ID	NPC279268
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IXWDYBPIGZKUPJ-MUCJXJSVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325773
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 72 76 0 0 0 0 0 0 0 0999 V2000 9.9314 -3.1995 0.3912 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0777 -2.0620 -0.4366 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9319 -1.3083 -0.6927 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6960 -1.6471 -0.1681 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5697 -0.8919 -0.4301 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6355 0.2342 -1.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8618 0.5634 -1.7441 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0022 -0.1855 -1.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2372 0.1594 -2.0181 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4045 0.9946 -1.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3938 2.1217 -2.2548 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2012 2.8257 -2.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1528 3.8543 -3.1743 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0408 2.3680 -1.8893 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8254 3.0019 -2.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6737 2.5370 -1.4683 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7403 1.3892 -0.6866 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9513 0.7752 -0.5358 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1187 1.2350 -1.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2625 0.6182 -0.9532 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4282 0.9638 -0.1260 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6547 -0.1421 0.7021 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1470 0.2627 2.0739 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5839 -0.9669 2.7992 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6683 -1.6685 2.0334 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6275 -1.4058 0.5667 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7827 -0.5098 0.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9724 -0.9155 0.6770 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0093 -0.0894 0.2578 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9695 -0.9526 -0.5344 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0381 -0.0636 -1.1220 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6026 0.8127 -0.0430 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0279 0.3402 1.2791 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6552 0.5168 1.3234 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2158 2.1402 -0.2231 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0132 -0.8519 -1.7301 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2044 -1.5497 -1.5590 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4372 -1.0320 0.0341 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7170 -3.0387 2.3470 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0038 -0.6471 4.1061 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0434 0.7776 2.7609 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7737 4.1591 -2.8445 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8901 -3.7062 0.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5068 -2.8219 1.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2380 -3.8936 -0.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6505 -2.5283 0.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6262 -1.1773 -0.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9593 1.4240 -2.3653 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9306 0.5090 -1.3438 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3018 2.4968 -2.7224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2895 3.0548 -1.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0551 -0.1218 0.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3323 -0.6649 0.8896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8817 1.0631 2.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7238 -1.6565 2.9187 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6469 -1.2558 2.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8803 -2.4065 0.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5402 0.5227 0.3996 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8998 -0.5323 -0.9798 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5989 0.6950 -0.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3626 -1.7781 0.0697 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5424 0.5856 -1.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6913 0.7837 -0.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2897 -0.6924 1.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4650 0.9896 2.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8812 2.6193 -0.7894 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5510 -1.2806 -1.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7237 -2.3212 -1.9066 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8497 -3.3454 2.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6791 0.0767 3.9983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2397 1.6466 2.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0865 4.1924 -3.6067 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 8 9 1 0 6 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 17 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 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 26 38 1 0 25 39 1 0 24 40 1 0 23 41 1 0 15 42 1 0 8 3 1 0 20 10 1 0 38 22 1 0 19 14 1 0 34 29 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 5 47 1 0 7 48 1 0 9 49 1 0 11 50 1 0 16 51 1 0 18 52 1 0 22 53 1 1 23 54 1 6 24 55 1 1 25 56 1 1 26 57 1 6 27 58 1 0 27 59 1 0 29 60 1 6 30 61 1 1 31 62 1 6 32 63 1 1 33 64 1 0 33 65 1 0 35 66 1 0 36 67 1 0 37 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	IXWDYBPIGZKUPJ-MUCJXJSVSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-37-16-3-2-10(4-12(16)28)17-7-14(30)20-13(29)5-11(6-18(20)41-17)40-27-25(36)23(34)22(33)19(42-27)9-39-26-24(35)21(32)15(31)8-38-26/h2-7,15,19,21-29,31-36H,8-9H2,1H3/t15-,19-,21+,22-,23+,24-,25-,26+,27-/m1/s1
SMILES	COc1ccc(cc1O)c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.753 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.15 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.756 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.643	Fsp³:	0.444
MCE-18:	115.923 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.645	Fluc inhibitor:	0.326 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.966 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.914 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.063	Promiscuous compounds:	0.38

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.289	MDCK Permeability:	-5.266
Pgp-inhibitor:	0.0	Pgp-substrate:	0.856
PAMPA:	0.995 ? 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):	0.894
20% Bioavailability (F20%):	0.139	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.268
Plasma Protein Binding (PPB):	77.656%	Volume Distribution (VD):	-0.229
Fu:	19.616% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.556
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.673
HLM stability:	0.001 ? 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):

1.436

Half-life (T1/2):

4.417

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.091
Human Hepatotoxicity (H-HT):	0.465	Drug-induced Liver Injury (DILI):	0.96
AMES Toxicity:	0.916	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.048	Skin Sensitization:	0.99
Carcinogencity:	0.096	Eye Corrosion:	0.0
Eye Irritation:	0.386	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.926
Hematotoxicity:	0.085	Drug-induced Nephrotoxicity:	0.617
Genotoxicity:	0.431	RPMI-8226 Immunitoxicity:	0.202
A549 Cytotoxicity:	0.284	Hek293 Cytotoxicity:	0.338
BCF:	0.353 ? 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:	2.861 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.366 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.529 ? 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
NPO5517	Rhododendron tomentosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32260539]
NPO5517	Rhododendron tomentosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5517	Rhododendron tomentosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5517	Rhododendron tomentosum	Species	Ericaceae	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 NPC279268 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	21127
0.1-0.2	24830
0.2-0.3	2840
0.3-0.4	662
0.4-0.5	276
0.5-0.6	77
0.6-0.7	32
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8605	High Similarity	NPC209296
0.7528	Intermediate Similarity	NPC22062
0.7528	Intermediate Similarity	NPC473634
0.7528	Intermediate Similarity	NPC138811
0.7326	Intermediate Similarity	NPC22832
0.7143	Intermediate Similarity	NPC210073
0.7033	Intermediate Similarity	NPC44931
0.7021	Intermediate Similarity	NPC473623
0.6947	Remote Similarity	NPC488089
0.6915	Remote Similarity	NPC65711
0.6739	Remote Similarity	NPC295613
0.6739	Remote Similarity	NPC473657
0.6632	Remote Similarity	NPC46202
0.6596	Remote Similarity	NPC473512
0.6596	Remote Similarity	NPC129827
0.6571	Remote Similarity	NPC198199
0.6465	Remote Similarity	NPC101636
0.6458	Remote Similarity	NPC284277
0.6458	Remote Similarity	NPC475497
0.6404	Remote Similarity	NPC181712
0.6389	Remote Similarity	NPC120952
0.6327	Remote Similarity	NPC229409
0.6327	Remote Similarity	NPC51326
0.6311	Remote Similarity	NPC472993
0.6292	Remote Similarity	NPC95090
0.6292	Remote Similarity	NPC27408
0.6289	Remote Similarity	NPC64051
0.6263	Remote Similarity	NPC270675
0.6263	Remote Similarity	NPC195685
0.6186	Remote Similarity	NPC204693
0.6154	Remote Similarity	NPC27942
0.6146	Remote Similarity	NPC15358
0.6139	Remote Similarity	NPC298171
0.6125	Remote Similarity	NPC223579
0.6117	Remote Similarity	NPC11468
0.6078	Remote Similarity	NPC472994
0.6064	Remote Similarity	NPC190003
0.6022	Remote Similarity	NPC243930
0.6	Remote Similarity	NPC19709
0.6	Remote Similarity	NPC483707
0.5957	Remote Similarity	NPC311830
0.5957	Remote Similarity	NPC607707
0.5934	Remote Similarity	NPC189142
0.5934	Remote Similarity	NPC77660
0.5914	Remote Similarity	NPC611303
0.5889	Remote Similarity	NPC331652
0.5859	Remote Similarity	NPC186816
0.5842	Remote Similarity	NPC473327
0.5833	Remote Similarity	NPC488087
0.5833	Remote Similarity	NPC211594
0.5824	Remote Similarity	NPC261866
0.5824	Remote Similarity	NPC39360
0.5824	Remote Similarity	NPC29763
0.5824	Remote Similarity	NPC210003
0.5816	Remote Similarity	NPC67105
0.5794	Remote Similarity	NPC473644
0.5773	Remote Similarity	NPC254540
0.5741	Remote Similarity	NPC311850
0.5728	Remote Similarity	NPC231194
0.5727	Remote Similarity	NPC488086
0.5714	Remote Similarity	NPC473043
0.5688	Remote Similarity	NPC488083
0.5684	Remote Similarity	NPC486578
0.5684	Remote Similarity	NPC601144
0.5684	Remote Similarity	NPC605067
0.567	Remote Similarity	NPC172807
0.5657	Remote Similarity	NPC275454
0.5657	Remote Similarity	NPC227508
0.5644	Remote Similarity	NPC488074
0.5586	Remote Similarity	NPC68592
0.5579	Remote Similarity	NPC191306
0.5579	Remote Similarity	NPC285197
0.5577	Remote Similarity	NPC475382
0.5556	Remote Similarity	NPC471079
0.5556	Remote Similarity	NPC51774
0.55	Remote Similarity	NPC67326
0.549	Remote Similarity	NPC475366
0.5472	Remote Similarity	NPC135358
0.5455	Remote Similarity	NPC8856
0.5455	Remote Similarity	NPC156977
0.5408	Remote Similarity	NPC276377
0.5398	Remote Similarity	NPC298666
0.5385	Remote Similarity	NPC606657
0.5306	Remote Similarity	NPC293004
0.5299	Remote Similarity	NPC262222
0.5294	Remote Similarity	NPC479405
0.5294	Remote Similarity	NPC303913
0.5283	Remote Similarity	NPC80068
0.5283	Remote Similarity	NPC195257
0.5283	Remote Similarity	NPC477629
0.5273	Remote Similarity	NPC480796
0.5248	Remote Similarity	NPC236191
0.5243	Remote Similarity	NPC115674
0.5243	Remote Similarity	NPC479404
0.5234	Remote Similarity	NPC235575
0.5221	Remote Similarity	NPC488088
0.5208	Remote Similarity	NPC229687
0.5204	Remote Similarity	NPC80188
0.5204	Remote Similarity	NPC608742
0.5196	Remote Similarity	NPC301683
0.5189	Remote Similarity	NPC142142
0.5189	Remote Similarity	NPC479766
0.5158	Remote Similarity	NPC58053
0.5152	Remote Similarity	NPC220169
0.5149	Remote Similarity	NPC251417
0.5146	Remote Similarity	NPC65003
0.5143	Remote Similarity	NPC479403
0.514	Remote Similarity	NPC479765
0.5098	Remote Similarity	NPC187379
0.5091	Remote Similarity	NPC121703
0.5089	Remote Similarity	NPC25523
0.506	Remote Similarity	NPC29353
0.5052	Remote Similarity	NPC186807
0.5052	Remote Similarity	NPC46420
0.505	Remote Similarity	NPC52353
0.5049	Remote Similarity	NPC142996
0.5047	Remote Similarity	NPC486577

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC279268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5236
0.1-0.2	3843
0.2-0.3	55
0.3-0.4	11
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD7054	Phase 4
0.66	Remote Similarity	NPD7472	Pre-clinical
0.5514	Remote Similarity	NPD7808	Phase 3
0.5429	Remote Similarity	NPD7251	Phase 2

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