NPASS Compound

Natural Product: NPC317672

Natural Product ID	NPC317672
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Demethyl Lonijaposide A
IUPAC Name	5-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(3-carboxypropyl)pyridin-1-ium-3-carboxylate
Synonyms	Demethyl Lonijaposide A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1928042
PubChem CID	56599664
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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 71 73 0 0 0 0 0 0 0 0999 V2000 -0.3806 0.0900 -3.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8402 -0.9462 -2.4098 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8863 -0.9532 -0.9267 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0702 -2.1313 -0.3568 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5654 -3.3417 -0.9350 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9167 -3.5315 -0.6844 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4740 -2.4931 0.0659 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3032 -1.1293 -0.3978 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5814 -0.3355 0.6860 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6958 0.4721 0.5162 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7792 0.1565 1.5364 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0004 0.9921 1.1934 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6082 2.1516 0.2775 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3031 2.7096 0.7453 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2957 1.7848 0.7313 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8985 3.9605 0.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9083 4.9094 0.0182 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6248 3.0987 0.3945 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9702 0.2629 0.5237 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3899 0.5076 2.8273 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0379 -4.3550 -1.7661 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2200 -4.4056 -2.1444 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7406 -5.4476 -2.2443 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2802 -1.8196 -0.0120 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4050 -2.4383 0.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7055 -1.8644 0.4134 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8392 -2.6417 0.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0508 -2.1382 0.7512 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1331 -0.8351 1.1668 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0499 -0.0543 1.2121 N 0 0 0 0 0 4 0 0 0 0 0 0 3.8476 -0.5529 0.8426 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1083 1.3188 1.6532 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3884 2.3106 0.5857 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4073 2.3854 -0.5336 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0756 2.7940 -0.0604 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8766 3.0864 1.1349 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9956 2.8676 -0.9299 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2835 -2.9362 0.7274 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2353 -4.1349 0.3502 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4890 -2.4126 1.1047 O 0 0 0 0 0 1 0 0 0 0 0 0 -0.3647 0.0537 -4.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0177 0.9801 -2.6020 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1999 -1.8292 -2.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4781 -0.0205 -0.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5654 -2.1491 0.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4063 -4.3911 -1.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9985 -1.0145 -1.2450 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1493 0.3190 -0.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0978 -0.9056 1.4934 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4442 1.4221 2.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5871 1.7968 -0.7656 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4477 3.0130 1.8206 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5325 3.7666 -1.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0476 4.4108 0.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6966 5.5886 -0.6756 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3936 2.7684 -0.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1046 -0.6216 0.9302 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0612 -0.2407 3.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4241 -5.9830 -3.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3870 -0.7347 0.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4590 -3.4768 -0.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7691 -3.6652 0.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1004 -0.4214 1.4681 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9974 0.1062 0.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9447 1.4387 2.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2020 1.6072 2.2119 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4413 2.2474 0.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3687 3.3239 1.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2661 1.4019 -1.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8053 3.0784 -1.3124 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0799 3.1701 -0.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 5 21 1 0 21 22 2 0 21 23 1 0 4 24 1 0 24 25 2 3 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 28 38 1 0 38 39 2 0 38 40 1 0 8 3 1 0 15 10 1 0 31 26 1 0 1 41 1 0 1 42 1 0 2 43 1 0 3 44 1 0 4 45 1 0 6 46 1 0 8 47 1 0 10 48 1 0 11 49 1 0 12 50 1 0 13 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 18 56 1 0 19 57 1 0 20 58 1 0 23 59 1 0 24 60 1 0 25 61 1 0 27 62 1 0 29 63 1 0 31 64 1 0 32 65 1 0 32 66 1 0 33 67 1 0 33 68 1 0 34 69 1 0 34 70 1 0 37 71 1 0 M CHG 2 30 1 40 -1 M END

Standard InCHIKey	SQWBLOVFMFTTHY-CUQQVVPFSA-N
Standard InCHI	InChI=1S/C26H31NO13/c1-2-15-16(6-5-13-8-14(23(34)35)10-27(9-13)7-3-4-19(29)30)17(24(36)37)12-38-25(15)40-26-22(33)21(32)20(31)18(11-28)39-26/h2,5-6,8-10,12,15-16,18,20-22,25-26,28,31-33H,1,3-4,7,11H2,(H2-,29,30,34,35,36,37)/b6-5+/t15-,16+,18-,20-,21+,22-,25+,26+/m1/s1
SMILES	C=CC1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)C=CC3=CC(=C[N+](=C3)CCCC(=O)O)C(=O)[O-]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	565.18	Volume:	534.124 ? Van der Waals volume.
Dense:	1.058	LogP:	-1.238 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.216 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.645 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	23.0
TPSA:	227.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	3.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.117	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.335	Fsp³:	0.462
MCE-18:	82.105 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.024	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.64 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.121	Promiscuous compounds:	0.008

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.855	MDCK Permeability:	-5.423
Pgp-inhibitor:	0.0	Pgp-substrate:	0.003
PAMPA:	1.0 ? 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):	0.961
20% Bioavailability (F20%):	0.176	30% Bioavailability (F30%):	0.762
50% Bioavailability (F50%):	0.426

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	36.673%	Volume Distribution (VD):	-0.638
Fu:	58.112% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.777	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.228	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

1.414

Half-life (T1/2):

2.157

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.205	Drug-induced Liver Injury (DILI):	0.156
AMES Toxicity:	0.218	Rat Oral Acute Toxicity:	0.51
Maximum Recommended Daily Dose:	0.846	Skin Sensitization:	1.0
Carcinogencity:	0.018	Eye Corrosion:	0.0
Eye Irritation:	0.557	Respiratory Toxicity:	0.033
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.982
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.15
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.157
BCF:	0.152 ? 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:	2.787 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.244 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.465 ? 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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

Activity Type	# Activity
Inhibition	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	<	30.0	%	PMID[21942812]

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 NPC317672 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	24447
0.1-0.2	23616
0.2-0.3	1720
0.3-0.4	38
0.4-0.5	19
0.5-0.6	10
0.6-0.7	6
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
0.7391	Intermediate Similarity	NPC322043
0.732	Intermediate Similarity	NPC32451
0.6489	Remote Similarity	NPC329024
0.6429	Remote Similarity	NPC25442
0.6429	Remote Similarity	NPC12944
0.6421	Remote Similarity	NPC59033
0.6354	Remote Similarity	NPC327373
0.6078	Remote Similarity	NPC111732
0.5938	Remote Similarity	NPC318020
0.5895	Remote Similarity	NPC325093
0.5842	Remote Similarity	NPC160127
0.5842	Remote Similarity	NPC50997
0.581	Remote Similarity	NPC328559
0.58	Remote Similarity	NPC324245
0.5743	Remote Similarity	NPC79223
0.5657	Remote Similarity	NPC182814
0.5294	Remote Similarity	NPC320748
0.5057	Remote Similarity	NPC600174

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC317672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5056
0.1-0.2	4043
0.2-0.3	51
0.3-0.4	0
0.4-0.5	0
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