NPASS Compound

Natural Product: NPC240592

Natural Product ID	NPC240592
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-O-P-Trans-Coumaroyl-8-O-Acetylshanzhiside Methyl Ester
IUPAC Name	methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500818
PubChem CID	24096431
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid 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 79 0 0 0 0 0 0 0 0999 V2000 -2.3918 -3.0364 -3.6171 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5610 -2.2743 -2.6344 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8192 -1.3680 -3.0784 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5676 -2.5123 -1.2848 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8097 -1.8273 -0.3185 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1396 -2.4404 1.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6845 -2.0594 -0.5102 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2509 -0.8003 0.1600 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3389 0.2515 -0.4289 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5093 1.5795 0.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2328 1.9151 1.2232 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1617 1.0177 1.6861 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8685 0.1820 0.7841 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0211 -0.3336 -0.3250 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0239 0.8454 0.3285 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1949 0.2391 0.7767 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8643 1.2220 1.7082 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0561 0.5009 2.3061 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9437 0.1321 1.1678 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2514 -0.5813 0.0462 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1210 -0.5492 -1.2043 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6469 -1.3987 -2.1859 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9957 -0.2085 -0.2332 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9988 -0.6391 1.6990 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7403 1.3822 3.1421 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9494 1.6045 2.6850 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5122 2.4917 -0.3299 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2415 2.2165 -1.2981 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6623 3.7249 0.2681 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6015 4.6907 -0.1624 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5477 -0.6009 -0.3319 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6732 -0.4916 0.4395 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5478 -0.5747 1.6874 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0111 -0.2842 -0.1027 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0639 -0.1842 0.6569 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4201 0.0229 0.1633 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4720 0.1164 1.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7876 0.3130 0.6558 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0812 0.4229 -0.6863 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0606 0.3343 -1.5901 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7388 0.1357 -1.1706 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3984 0.6211 -1.1128 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8770 -3.1632 -4.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2761 -2.3721 -3.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7945 -3.9493 -3.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5998 -3.4343 1.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6814 -1.8864 1.8756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1949 -2.6877 1.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9632 -2.0483 -1.5774 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0357 -2.9703 -0.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1924 -0.8658 1.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6389 0.3492 -1.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1036 2.8835 1.6792 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2370 -0.6688 1.3927 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5756 -0.0963 -1.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9084 -0.6365 1.3966 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2276 2.1052 1.1531 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7515 -0.4166 2.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4097 1.0557 0.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2318 -1.6722 0.3497 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2504 0.4514 -1.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1451 -0.9378 -0.9274 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5965 -2.3451 -1.8404 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8744 -0.2985 1.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0818 2.0693 3.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9193 2.5964 2.7875 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7480 4.5877 -1.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2120 5.6908 0.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5817 4.5807 0.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0980 -0.2155 -1.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8982 -0.2634 1.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2170 0.0265 2.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5743 0.3794 1.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3040 0.4217 -2.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9597 0.0703 -1.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0695 -0.1376 -0.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 5 4 1 6 5 6 1 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 19 24 1 0 18 25 1 0 17 26 1 0 10 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 8 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 14 5 1 0 23 16 1 0 41 36 1 0 14 9 1 0 1 43 1 0 1 44 1 0 1 45 1 0 6 46 1 0 6 47 1 0 6 48 1 0 7 49 1 0 7 50 1 0 8 51 1 1 9 52 1 6 11 53 1 0 13 54 1 1 14 55 1 6 16 56 1 1 17 57 1 6 18 58 1 1 19 59 1 6 20 60 1 1 21 61 1 0 21 62 1 0 22 63 1 0 24 64 1 0 25 65 1 0 26 66 1 0 30 67 1 0 30 68 1 0 30 69 1 0 34 70 1 0 35 71 1 0 37 72 1 0 38 73 1 0 40 74 1 0 41 75 1 0 42 76 1 0 M END

Standard InCHIKey	VWZXXWQOKCWKSB-PSVLUTBBSA-N
Standard InCHI	InChI=1S/C28H34O14/c1-13(30)42-28(2)10-17(39-19(32)9-6-14-4-7-15(31)8-5-14)20-16(25(36)37-3)12-38-26(21(20)28)41-27-24(35)23(34)22(33)18(11-29)40-27/h4-9,12,17-18,20-24,26-27,29,31,33-35H,10-11H2,1-3H3/b9-6+/t17-,18-,20+,21-,22-,23+,24-,26+,27+,28+/m1/s1
SMILES	CC(=O)O[C@@]1(C)C[C@H]([C@@H]2C(=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC)OC(=O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.19	Volume:	560.59 ? Van der Waals volume.
Dense:	1.06	LogP:	1.35 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.735 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.172 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	26.0
TPSA:	207.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.972	Fsp³:	0.536
MCE-18:	105.349 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.853	Fluc inhibitor:	0.605 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.245 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.249 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.126	Promiscuous compounds:	0.487

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.006	MDCK Permeability:	-5.218
Pgp-inhibitor:	0.033	Pgp-substrate:	0.027
PAMPA:	0.961 ? 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):	0.145
20% Bioavailability (F20%):	0.917	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.194
Plasma Protein Binding (PPB):	67.767%	Volume Distribution (VD):	-0.359
Fu:	30.999% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.459

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.974
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.092 ? 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):

2.283

Half-life (T1/2):

2.579

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.171
Human Hepatotoxicity (H-HT):	0.694	Drug-induced Liver Injury (DILI):	0.968
AMES Toxicity:	0.907	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.125	Skin Sensitization:	1.0
Carcinogencity:	0.138	Eye Corrosion:	0.0
Eye Irritation:	0.063	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.076	Ototoxicity:	0.915
Hematotoxicity:	0.309	Drug-induced Nephrotoxicity:	0.899
Genotoxicity:	0.769	RPMI-8226 Immunitoxicity:	0.102
A549 Cytotoxicity:	0.201	Hek293 Cytotoxicity:	0.444
BCF:	0.616 ? 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:	3.334 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.09 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.386 ? 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
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	aerial part	purchased in Vung Tau, Vietnam	2012-MAR	PMID[25611215]
NPO17110	Barleria prionitis	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784173]
NPO17110	Barleria prionitis	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17110	Barleria prionitis	Species	Acanthaceae	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
EC50	1
Ratio IC50/EC50	1

Activity Type	# Activity
Organism	1
Others	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
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	=	2.46	ug.mL-1	PMID[12166949]
NPT2	Others	Unspecified	n.a.	Ratio IC50/EC50	=	17.0	n.a.	PMID[12166949]

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 NPC240592 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	8705
0.1-0.2	35105
0.2-0.3	5192
0.3-0.4	662
0.4-0.5	163
0.5-0.6	21
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC117346
0.7093	Intermediate Similarity	NPC96599
0.6923	Remote Similarity	NPC63304
0.6818	Remote Similarity	NPC31745
0.6818	Remote Similarity	NPC220936
0.6374	Remote Similarity	NPC202391
0.6374	Remote Similarity	NPC296659
0.6105	Remote Similarity	NPC203664
0.6087	Remote Similarity	NPC475484
0.5806	Remote Similarity	NPC475379
0.5699	Remote Similarity	NPC46644
0.5638	Remote Similarity	NPC475213
0.5638	Remote Similarity	NPC152796
0.5591	Remote Similarity	NPC474620
0.5532	Remote Similarity	NPC49597
0.5532	Remote Similarity	NPC475539
0.5532	Remote Similarity	NPC143246
0.5521	Remote Similarity	NPC475378
0.5417	Remote Similarity	NPC479970
0.5316	Remote Similarity	NPC11724
0.5104	Remote Similarity	NPC169398
0.51	Remote Similarity	NPC180586
0.5053	Remote Similarity	NPC145287
0.5052	Remote Similarity	NPC18789
0.505	Remote Similarity	NPC229548
0.505	Remote Similarity	NPC286919
0.505	Remote Similarity	NPC475663
0.5049	Remote Similarity	NPC184464
0.5049	Remote Similarity	NPC251062
0.5048	Remote Similarity	NPC179914

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC240592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4539
0.1-0.2	4525
0.2-0.3	84
0.3-0.4	2
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