NPASS Compound

Natural Product: NPC158187

Natural Product ID	NPC158187
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JXRZMKWWELOXOG-RYDBIISISA-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 76 80 0 0 0 0 0 0 0 0999 V2000 6.6095 -5.8446 0.5430 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3613 -6.0362 1.1969 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3601 -5.0680 1.0500 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1139 -5.2125 1.5888 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1439 -4.2522 1.4513 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4398 -3.0873 0.7393 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6768 -2.8941 0.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6347 -3.9004 0.3408 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9949 -1.8145 -0.4831 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1271 -0.7999 -0.6633 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5704 0.3598 -1.4168 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9617 0.4898 -1.6254 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4804 1.5242 -2.3665 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7023 2.4718 -2.9358 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2871 2.3954 -2.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7919 1.3148 -1.9937 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5464 3.2840 -3.3008 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3899 3.8865 -3.6318 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1561 3.5376 -3.6910 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9083 -0.9353 -0.1308 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5070 -2.0900 0.5932 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3687 -2.1873 1.0680 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9211 0.0439 -0.2056 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6545 0.7576 0.9766 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9180 2.2095 1.0683 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2939 2.8059 0.3994 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3205 1.6768 0.5437 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8159 1.2542 -0.8070 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7406 0.2551 -0.7378 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8743 0.5938 -0.0692 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1175 0.4879 -0.9613 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2178 1.2245 -0.2064 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4881 0.3497 1.0222 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1649 0.2736 1.7645 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2951 -0.5028 3.0583 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5681 -1.8349 2.8505 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1411 -0.2615 1.0127 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4146 0.9005 1.8698 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3356 1.4562 -0.9656 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9034 1.0053 -2.2190 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7393 0.6498 1.2566 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7154 3.9751 1.0374 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1207 2.6785 0.6361 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8765 -4.3939 1.9940 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1345 -4.9920 0.9952 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1514 -6.8084 0.6483 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3965 -5.5948 -0.5139 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8696 -6.1161 2.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5952 -3.7622 -0.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6055 -0.2343 -1.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5719 1.6033 -2.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7162 1.2489 -1.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5277 3.2374 -3.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2258 4.0520 -4.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3104 4.8815 -3.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9340 4.1050 -3.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1857 0.2785 1.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8345 2.4805 2.1960 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0413 2.9679 -0.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1585 2.1365 1.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1961 2.1595 -1.3643 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9043 0.8945 -1.3753 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8580 1.6241 0.3225 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4016 -0.5696 -1.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8120 2.1847 0.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7738 -0.6588 0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8703 1.3137 2.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3263 -0.3827 3.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0688 -0.0603 3.6997 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1343 -2.0132 2.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2433 1.1011 1.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0891 0.8440 -0.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9853 0.9249 -2.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6668 3.7838 1.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3147 3.5784 0.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6793 -4.9544 2.8120 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 14 19 1 0 10 20 2 0 20 21 1 0 21 22 2 0 20 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 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 27 41 1 0 26 42 1 0 25 43 1 0 5 44 1 0 8 3 1 0 16 11 1 0 41 24 1 0 21 6 1 0 37 30 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 8 49 1 0 12 50 1 0 13 51 1 0 16 52 1 0 18 53 1 0 18 54 1 0 18 55 1 0 19 56 1 0 24 57 1 1 25 58 1 1 26 59 1 6 27 60 1 1 28 61 1 0 28 62 1 0 30 63 1 1 31 64 1 6 32 65 1 1 33 66 1 6 34 67 1 1 35 68 1 0 35 69 1 0 36 70 1 0 38 71 1 0 39 72 1 0 40 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	JXRZMKWWELOXOG-RYDBIISISA-N
Standard InCHI	InChI=1S/C28H32O16/c1-38-11-6-13(31)18-15(7-11)41-25(10-3-4-12(30)14(5-10)39-2)26(21(18)34)44-28-23(36)20(33)17(43-28)9-40-27-24(37)22(35)19(32)16(8-29)42-27/h3-7,16-17,19-20,22-24,27-33,35-37H,8-9H2,1-2H3/t16-,17-,19-,20-,22+,23+,24-,27-,28+/m1/s1
SMILES	COc1cc(c2c(c1)oc(c1ccc(c(c1)OC)O)c(c2=O)O[C@H]1[C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.894 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.505 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.401 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	29.0
TPSA:	247.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.135	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.607	Fsp³:	0.464
MCE-18:	116.927 ? 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:	0.646	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.914 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.617 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.055	Promiscuous compounds:	0.423

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.328	MDCK Permeability:	-5.369
Pgp-inhibitor:	0.005	Pgp-substrate:	0.373
PAMPA:	0.872 ? 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):	0.995
20% Bioavailability (F20%):	0.141	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.066
Plasma Protein Binding (PPB):	81.483%	Volume Distribution (VD):	-0.102
Fu:	17.619% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.95
BSEP inhibitor:	0.012

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.975
HLM stability:	0.314 ? 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):

1.864

Half-life (T1/2):

3.482

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.646	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.977	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.041	Skin Sensitization:	1.0
Carcinogencity:	0.224	Eye Corrosion:	0.0
Eye Irritation:	0.119	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.951
Hematotoxicity:	0.36	Drug-induced Nephrotoxicity:	0.676
Genotoxicity:	0.584	RPMI-8226 Immunitoxicity:	0.224
A549 Cytotoxicity:	0.866	Hek293 Cytotoxicity:	0.65
BCF:	0.453 ? 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:	3.072 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.602 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.749 ? 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
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7873	Artemisia sibirica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11067	Buxus papillosa	Species	Buxaceae	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 NPC158187 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	23586
0.1-0.2	22011
0.2-0.3	3148
0.3-0.4	599
0.4-0.5	322
0.5-0.6	153
0.6-0.7	34
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
0.6979	Remote Similarity	NPC476472
0.6979	Remote Similarity	NPC294815
0.6979	Remote Similarity	NPC16194
0.6809	Remote Similarity	NPC186816
0.6737	Remote Similarity	NPC488073
0.6703	Remote Similarity	NPC203050
0.6703	Remote Similarity	NPC488072
0.6703	Remote Similarity	NPC225434
0.6591	Remote Similarity	NPC297987
0.6591	Remote Similarity	NPC136042
0.6526	Remote Similarity	NPC156869
0.6517	Remote Similarity	NPC84362
0.6505	Remote Similarity	NPC480441
0.6505	Remote Similarity	NPC25523
0.6484	Remote Similarity	NPC101026
0.6484	Remote Similarity	NPC488077
0.6413	Remote Similarity	NPC311830
0.6392	Remote Similarity	NPC153755
0.6344	Remote Similarity	NPC601586
0.6292	Remote Similarity	NPC289667
0.6286	Remote Similarity	NPC277532
0.6237	Remote Similarity	NPC116458
0.6237	Remote Similarity	NPC246943
0.6237	Remote Similarity	NPC605784
0.6214	Remote Similarity	NPC121703
0.62	Remote Similarity	NPC142142
0.6162	Remote Similarity	NPC470443
0.6154	Remote Similarity	NPC46420
0.6154	Remote Similarity	NPC271692
0.6091	Remote Similarity	NPC488079
0.6082	Remote Similarity	NPC275454
0.6064	Remote Similarity	NPC206123
0.6058	Remote Similarity	NPC89052
0.6042	Remote Similarity	NPC251417
0.5982	Remote Similarity	NPC192539
0.5976	Remote Similarity	NPC78326
0.5957	Remote Similarity	NPC601144
0.5943	Remote Similarity	NPC173837
0.59	Remote Similarity	NPC126784
0.59	Remote Similarity	NPC240306
0.59	Remote Similarity	NPC241423
0.5895	Remote Similarity	NPC223747
0.5882	Remote Similarity	NPC486577
0.5851	Remote Similarity	NPC611303
0.581	Remote Similarity	NPC14187
0.58	Remote Similarity	NPC473571
0.58	Remote Similarity	NPC110941
0.5794	Remote Similarity	NPC219043
0.5784	Remote Similarity	NPC209296
0.5784	Remote Similarity	NPC35119
0.5784	Remote Similarity	NPC473327
0.5761	Remote Similarity	NPC249281
0.5758	Remote Similarity	NPC173582
0.5758	Remote Similarity	NPC265885
0.5758	Remote Similarity	NPC181465
0.5758	Remote Similarity	NPC215710
0.5758	Remote Similarity	NPC67105
0.5758	Remote Similarity	NPC473438
0.5758	Remote Similarity	NPC253788
0.5743	Remote Similarity	NPC64425
0.5743	Remote Similarity	NPC488074
0.5741	Remote Similarity	NPC217520
0.5701	Remote Similarity	NPC189564
0.57	Remote Similarity	NPC203259
0.57	Remote Similarity	NPC33054
0.57	Remote Similarity	NPC210073
0.57	Remote Similarity	NPC176740
0.57	Remote Similarity	NPC471725
0.57	Remote Similarity	NPC134532
0.57	Remote Similarity	NPC602582
0.5699	Remote Similarity	NPC158674
0.5684	Remote Similarity	NPC488071
0.5673	Remote Similarity	NPC220173
0.567	Remote Similarity	NPC276377
0.5664	Remote Similarity	NPC470720
0.5657	Remote Similarity	NPC471079
0.5648	Remote Similarity	NPC292019
0.5648	Remote Similarity	NPC202908
0.5638	Remote Similarity	NPC24043
0.5636	Remote Similarity	NPC139571
0.5631	Remote Similarity	NPC32641
0.5631	Remote Similarity	NPC256188
0.5625	Remote Similarity	NPC486578
0.5607	Remote Similarity	NPC203145
0.56	Remote Similarity	NPC44931
0.56	Remote Similarity	NPC67326
0.5579	Remote Similarity	NPC42773
0.5579	Remote Similarity	NPC45522
0.5579	Remote Similarity	NPC325555
0.5579	Remote Similarity	NPC226304
0.5575	Remote Similarity	NPC470717
0.5566	Remote Similarity	NPC135358
0.5545	Remote Similarity	NPC22062
0.5545	Remote Similarity	NPC479405
0.5545	Remote Similarity	NPC473634
0.5545	Remote Similarity	NPC138811
0.5545	Remote Similarity	NPC150164
0.5536	Remote Similarity	NPC295625
0.5532	Remote Similarity	NPC277205
0.5532	Remote Similarity	NPC37919
0.5526	Remote Similarity	NPC488078
0.5524	Remote Similarity	NPC195257
0.5524	Remote Similarity	NPC473073
0.549	Remote Similarity	NPC479404
0.5478	Remote Similarity	NPC209550
0.5474	Remote Similarity	NPC488080
0.5474	Remote Similarity	NPC169977
0.5472	Remote Similarity	NPC292929
0.5464	Remote Similarity	NPC22832
0.5464	Remote Similarity	NPC120099
0.5439	Remote Similarity	NPC470719
0.5426	Remote Similarity	NPC77672
0.5426	Remote Similarity	NPC133671
0.5426	Remote Similarity	NPC135391
0.5426	Remote Similarity	NPC78263
0.5426	Remote Similarity	NPC250069
0.5421	Remote Similarity	NPC470446
0.5421	Remote Similarity	NPC602448
0.5417	Remote Similarity	NPC472459
0.5413	Remote Similarity	NPC473072
0.5408	Remote Similarity	NPC602805
0.5392	Remote Similarity	NPC65563
0.5392	Remote Similarity	NPC470949
0.5385	Remote Similarity	NPC65711
0.5385	Remote Similarity	NPC479403
0.5368	Remote Similarity	NPC145038
0.5368	Remote Similarity	NPC56077
0.5368	Remote Similarity	NPC281131
0.5368	Remote Similarity	NPC253662
0.5368	Remote Similarity	NPC179950
0.5368	Remote Similarity	NPC323593
0.5368	Remote Similarity	NPC88789
0.5368	Remote Similarity	NPC203500
0.5368	Remote Similarity	NPC189142
0.5368	Remote Similarity	NPC77660
0.5368	Remote Similarity	NPC491374
0.5361	Remote Similarity	NPC285197
0.5351	Remote Similarity	NPC198199
0.5347	Remote Similarity	NPC480466
0.5347	Remote Similarity	NPC29958
0.5347	Remote Similarity	NPC139320
0.5347	Remote Similarity	NPC609888
0.5345	Remote Similarity	NPC138990
0.5333	Remote Similarity	NPC606657
0.5327	Remote Similarity	NPC470449
0.5315	Remote Similarity	NPC164704
0.5312	Remote Similarity	NPC603655
0.5306	Remote Similarity	NPC21666
0.5299	Remote Similarity	NPC175429
0.5294	Remote Similarity	NPC471748
0.5294	Remote Similarity	NPC39834
0.5294	Remote Similarity	NPC227508
0.5263	Remote Similarity	NPC39360
0.5263	Remote Similarity	NPC29763
0.5263	Remote Similarity	NPC210003
0.5258	Remote Similarity	NPC599850
0.5253	Remote Similarity	NPC607707
0.5243	Remote Similarity	NPC102028
0.5221	Remote Similarity	NPC470716
0.5214	Remote Similarity	NPC120952
0.5208	Remote Similarity	NPC8573
0.5208	Remote Similarity	NPC64305
0.5208	Remote Similarity	NPC95090
0.5208	Remote Similarity	NPC27408
0.5204	Remote Similarity	NPC60735
0.5204	Remote Similarity	NPC26230
0.52	Remote Similarity	NPC469931
0.5189	Remote Similarity	NPC473623
0.5189	Remote Similarity	NPC72016
0.5179	Remote Similarity	NPC470715
0.5169	Remote Similarity	NPC37074
0.5152	Remote Similarity	NPC243930
0.5152	Remote Similarity	NPC609478
0.5149	Remote Similarity	NPC116864
0.5149	Remote Similarity	NPC244776
0.514	Remote Similarity	NPC488089
0.5133	Remote Similarity	NPC311850
0.5111	Remote Similarity	NPC287780
0.5111	Remote Similarity	NPC60982
0.5106	Remote Similarity	NPC288084
0.5098	Remote Similarity	NPC473682
0.5089	Remote Similarity	NPC48984
0.5088	Remote Similarity	NPC488083
0.5053	Remote Similarity	NPC67037
0.5053	Remote Similarity	NPC255615
0.5047	Remote Similarity	NPC229409
0.5046	Remote Similarity	NPC470445

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5792
0.1-0.2	3297
0.2-0.3	50
0.3-0.4	5
0.4-0.5	2
0.5-0.6	2
0.6-0.7	2
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
0.6633	Remote Similarity	NPD7251	Phase 2
0.6373	Remote Similarity	NPD7808	Phase 3
0.5784	Remote Similarity	NPD7054	Phase 4
0.57	Remote Similarity	NPD6797	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