NPASS Compound

Natural Product: NPC288426

Natural Product ID	NPC288426
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OPOXKCGDGZJWHI-UJGPHIHISA-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:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid 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 59 62 0 0 0 0 0 0 0 0999 V2000 6.7788 2.5321 -2.5721 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3211 1.5727 -1.6661 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5358 0.7509 -0.8848 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1688 0.8021 -0.9275 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4069 -0.0290 -0.1374 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0585 -0.9105 0.6944 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4158 -0.9876 0.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1580 -0.1342 -0.0495 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5438 -0.2447 0.0493 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0439 -1.8804 1.6041 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2484 -2.7266 2.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9359 0.0209 -0.1785 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2312 1.2000 -0.1672 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9245 1.2377 -0.2038 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2169 0.1383 -0.2535 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1828 0.2393 -0.2911 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9615 -0.8922 -0.3437 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2701 -2.1069 -0.3563 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0780 -2.2479 -0.3213 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8421 -1.0901 -0.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2194 -1.1493 -0.2303 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8386 -2.2610 -0.2422 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7286 -3.4765 -0.3354 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3322 -0.9282 -0.3841 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1289 0.2085 -0.3767 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0052 0.1976 -1.6450 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4083 -0.1253 -1.2381 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9678 0.8981 -0.2712 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8480 1.2972 0.6543 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4439 1.6374 2.0108 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1385 0.5708 2.5572 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9666 0.2393 0.7555 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5007 1.9814 -0.9504 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4412 -1.3811 -0.6683 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9064 1.4065 -2.3250 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6559 3.0989 -2.9781 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2433 2.0058 -3.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1386 3.2012 -1.9762 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6654 1.5135 -1.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4585 -1.5631 1.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1125 0.5099 -0.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8917 -3.5144 2.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7890 -2.1087 3.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4806 -3.2620 1.7964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7590 2.1459 -0.1268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6366 1.2204 -0.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8678 -3.0085 -0.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5865 -4.0413 -1.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5649 1.1535 -0.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6621 -0.5978 -2.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0705 -0.1422 -2.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7460 0.3871 0.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3046 2.1961 0.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1448 2.4908 1.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6337 1.9870 2.7048 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0969 0.7083 2.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3008 1.8766 -1.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7163 -1.9525 -1.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2288 1.3361 -3.0250 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 7 10 1 0 10 11 1 0 5 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 19 23 1 0 17 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 29 32 1 0 28 33 1 0 27 34 1 0 26 35 1 0 8 3 1 0 21 12 1 0 32 25 1 0 20 15 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 6 40 1 0 9 41 1 0 11 42 1 0 11 43 1 0 11 44 1 0 13 45 1 0 16 46 1 0 18 47 1 0 23 48 1 0 25 49 1 6 26 50 1 6 27 51 1 6 28 52 1 1 29 53 1 6 30 54 1 0 30 55 1 0 31 56 1 0 33 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	OPOXKCGDGZJWHI-UJGPHIHISA-N
Standard InCHI	InChI=1S/C23H24O12/c1-31-14-3-9(4-15(32-2)19(14)27)11-8-33-13-6-10(5-12(25)17(13)18(11)26)34-23-22(30)21(29)20(28)16(7-24)35-23/h3-6,8,16,20-25,27-30H,7H2,1-2H3/t16-,20-,21+,22-,23-/m1/s1
SMILES	COc1cc(cc(c1O)OC)c1coc2cc(cc(c2c1=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.13	Volume:	456.529 ? Van der Waals volume.
Dense:	1.078	LogP:	0.505 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.057 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.055 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	188.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.982	Fsp³:	0.348
MCE-18:	89.71 ? 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:	0.521	Fluc inhibitor:	0.189 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.897 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.823 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.098	Promiscuous compounds:	0.568

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.21	MDCK Permeability:	-5.47
Pgp-inhibitor:	0.003	Pgp-substrate:	0.549
PAMPA:	0.953 ? 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):	0.805
20% Bioavailability (F20%):	0.03	30% Bioavailability (F30%):	0.966
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.416
Plasma Protein Binding (PPB):	85.194%	Volume Distribution (VD):	-0.277
Fu:	14.281% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.84
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.013	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.098	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.165
HLM stability:	0.05 ? 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):

3.126

Half-life (T1/2):

3.856

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.127
Human Hepatotoxicity (H-HT):	0.69	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.886	Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.075	Skin Sensitization:	0.944
Carcinogencity:	0.416	Eye Corrosion:	0.0
Eye Irritation:	0.134	Respiratory Toxicity:	0.045
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.919
Hematotoxicity:	0.327	Drug-induced Nephrotoxicity:	0.762
Genotoxicity:	0.776	RPMI-8226 Immunitoxicity:	0.195
A549 Cytotoxicity:	0.348	Hek293 Cytotoxicity:	0.312
BCF:	0.434 ? 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:	3.137 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.503 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.692 ? 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
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7639	Senecio isatideus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14100	Persea kusanoi	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2263	Croton megistocarpus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8075	Cacospongia scalaris	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO433	Geranium sibiricum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7639	Senecio isatideus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4593	Lagerstroemia indica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4582	Baphicacanthus cusia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8075	Cacospongia scalaris	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2263	Croton megistocarpus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14100	Persea kusanoi	Species	Lauraceae	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 NPC288426 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	24174
0.1-0.2	21904
0.2-0.3	2633
0.3-0.4	853
0.4-0.5	216
0.5-0.6	56
0.6-0.7	16
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
0.7973	Intermediate Similarity	NPC73511
0.7838	Intermediate Similarity	NPC197896
0.7838	Intermediate Similarity	NPC313163
0.7368	Intermediate Similarity	NPC234739
0.7089	Intermediate Similarity	NPC80140
0.6667	Remote Similarity	NPC481043
0.6667	Remote Similarity	NPC224462
0.6667	Remote Similarity	NPC160515
0.6628	Remote Similarity	NPC479405
0.6627	Remote Similarity	NPC48773
0.6582	Remote Similarity	NPC348541
0.6552	Remote Similarity	NPC479404
0.6429	Remote Similarity	NPC479407
0.6341	Remote Similarity	NPC205076
0.631	Remote Similarity	NPC307518
0.6296	Remote Similarity	NPC156457
0.619	Remote Similarity	NPC229729
0.6145	Remote Similarity	NPC100720
0.6092	Remote Similarity	NPC487212
0.6049	Remote Similarity	NPC45165
0.6044	Remote Similarity	NPC479403
0.5952	Remote Similarity	NPC138540
0.5904	Remote Similarity	NPC105511
0.5904	Remote Similarity	NPC95090
0.5904	Remote Similarity	NPC161749
0.5904	Remote Similarity	NPC27408
0.5897	Remote Similarity	NPC191154
0.5882	Remote Similarity	NPC479402
0.5854	Remote Similarity	NPC135345
0.5823	Remote Similarity	NPC134819
0.5814	Remote Similarity	NPC22832
0.5814	Remote Similarity	NPC243930
0.5747	Remote Similarity	NPC311830
0.5747	Remote Similarity	NPC607201
0.5714	Remote Similarity	NPC303913
0.5647	Remote Similarity	NPC84362
0.5632	Remote Similarity	NPC486578
0.5595	Remote Similarity	NPC289667
0.5581	Remote Similarity	NPC60966
0.5568	Remote Similarity	NPC479406
0.5568	Remote Similarity	NPC607707
0.5529	Remote Similarity	NPC487213
0.5529	Remote Similarity	NPC258035
0.5526	Remote Similarity	NPC114192
0.5517	Remote Similarity	NPC479401
0.5517	Remote Similarity	NPC285197
0.5506	Remote Similarity	NPC601586
0.5455	Remote Similarity	NPC601144
0.5455	Remote Similarity	NPC601607
0.5412	Remote Similarity	NPC261866
0.5412	Remote Similarity	NPC39360
0.5412	Remote Similarity	NPC29763
0.5412	Remote Similarity	NPC210003
0.5349	Remote Similarity	NPC297987
0.5349	Remote Similarity	NPC277205
0.5349	Remote Similarity	NPC37919
0.5349	Remote Similarity	NPC136042
0.5349	Remote Similarity	NPC323593
0.5349	Remote Similarity	NPC203500
0.5349	Remote Similarity	NPC189142
0.5349	Remote Similarity	NPC77660
0.5287	Remote Similarity	NPC22195
0.5287	Remote Similarity	NPC21190
0.5287	Remote Similarity	NPC603655
0.5281	Remote Similarity	NPC610187
0.527	Remote Similarity	NPC116632
0.5227	Remote Similarity	NPC222936
0.5227	Remote Similarity	NPC325555
0.5227	Remote Similarity	NPC226304
0.5217	Remote Similarity	NPC251417
0.52	Remote Similarity	NPC303644
0.5172	Remote Similarity	NPC603782
0.5169	Remote Similarity	NPC307938
0.5063	Remote Similarity	NPC99515
0.5055	Remote Similarity	NPC116458
0.5055	Remote Similarity	NPC246943
0.5055	Remote Similarity	NPC605784

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC288426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5465
0.1-0.2	3613
0.2-0.3	57
0.3-0.4	10
0.4-0.5	4
0.5-0.6	1
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
0.5904	Remote Similarity	NPD4381	Clinical (unspecified phase)

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