NPASS Compound

Natural Product: NPC482302

Natural Product ID	NPC482302
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LOFAXWYWIGZHPN-PSLQACODSA-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]

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 84 86 0 0 0 0 0 0 0 0999 V2000 -2.4432 -3.6984 -0.1753 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2763 -2.2190 -0.0693 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2198 -1.5605 0.8428 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0540 -0.6447 0.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0239 0.0716 1.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2905 -0.6874 2.4875 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2367 0.4009 0.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2743 1.3567 1.5892 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9323 2.3761 1.5016 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8705 1.3256 2.0102 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8786 1.4029 0.8851 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4853 1.1200 1.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1120 0.9964 2.4958 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5417 0.9823 0.1713 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3142 -0.0849 -0.8235 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4844 -0.1332 -1.7744 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2494 -1.4313 -2.5230 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5191 -2.2432 -2.6924 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2087 -2.1613 -1.7420 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2202 -1.5094 -0.3732 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9123 -1.8906 0.4478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8211 -1.9659 1.6608 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4024 -1.7965 0.3491 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6293 -3.0473 0.9118 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7257 -3.8810 0.7295 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8450 -3.3768 1.6715 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7429 -0.3103 -1.1507 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8417 0.4736 -1.4436 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6927 1.3624 -2.2929 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1126 0.2504 -0.7728 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2313 1.0262 -1.0508 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4483 0.8389 -0.4318 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5425 -0.1687 0.5032 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4599 -0.9690 0.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2744 -0.7354 0.1678 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4013 2.2274 -0.5490 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3966 3.1730 -0.5711 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4479 2.9215 0.0700 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2089 4.4371 -1.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9388 2.7354 0.3272 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3433 2.9316 -0.9552 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6702 1.9359 -1.6668 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4121 4.2965 -1.5480 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6412 2.4255 2.8788 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0170 -4.1209 -1.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0014 -4.2221 0.7231 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5217 -3.9581 -0.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3987 -1.8326 -1.1210 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2592 -1.7892 1.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0725 -0.3976 -0.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3727 -0.6174 3.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5047 -1.7476 2.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0923 -0.1922 3.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9296 0.5215 -0.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7743 1.2759 0.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8989 -0.5056 0.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6898 0.4397 2.6660 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2132 0.7496 0.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9199 0.7861 2.7904 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8298 1.0967 3.2854 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5434 0.8886 0.6221 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5704 0.1689 -1.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5042 0.7297 -2.4838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9218 -1.1574 -3.5474 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0543 -2.0061 -3.6333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2485 -3.3369 -2.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1814 -2.0550 -1.8423 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2995 -3.2410 -1.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7568 -1.8946 -2.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6853 -3.5647 0.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6710 -4.3317 2.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1071 -2.5602 2.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1320 1.8056 -1.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3211 1.4553 -0.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4662 -0.3467 1.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5649 -1.7673 1.5685 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4288 -1.3544 0.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6325 5.1903 -0.7968 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7025 4.1881 -2.2890 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2037 4.8693 -1.6398 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6861 4.4066 -2.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4384 4.3703 -2.0134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3817 5.0795 -0.7786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2835 2.4245 3.6074 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 1 0 5 7 1 0 5 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 20 23 1 1 23 24 1 0 24 25 2 0 24 26 1 0 16 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 14 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 11 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 10 44 1 0 21 2 1 0 35 30 1 0 20 15 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 6 3 49 1 0 4 50 1 0 6 51 1 0 6 52 1 0 6 53 1 0 7 54 1 0 7 55 1 0 7 56 1 0 10 57 1 1 11 58 1 6 13 59 1 0 13 60 1 0 14 61 1 1 15 62 1 6 16 63 1 6 17 64 1 6 18 65 1 0 18 66 1 0 18 67 1 0 19 68 1 0 19 69 1 0 26 70 1 0 26 71 1 0 26 72 1 0 31 73 1 0 32 74 1 0 33 75 1 0 34 76 1 0 35 77 1 0 39 78 1 0 39 79 1 0 39 80 1 0 43 81 1 0 43 82 1 0 43 83 1 0 44 84 1 0 M END

Standard InCHIKey	LOFAXWYWIGZHPN-PSLQACODSA-N
Standard InCHI	InChI=1S/C33H40O11/c1-17-14-15-32(7,8)30(39)25(37)28(42-21(5)35)19(3)27(41-20(4)34)24-26(43-31(40)23-12-10-9-11-13-23)18(2)16-33(24,29(17)38)44-22(6)36/h9-15,17-18,24-28,37H,3,16H2,1-2,4-8H3/b15-14+/t17-,18-,24+,25+,26-,27-,28-,33+/m0/s1
SMILES	C[C@H]1/C=C/C(C)(C)C(=O)[C@@H]([C@H](C(=C)[C@@H]([C@H]2[C@H]([C@@H](C)C[C@@]2(C1=O)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	612.26	Volume:	621.346 ? Van der Waals volume.
Dense:	0.985	LogP:	2.112 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.443 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.746 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	29.0
TPSA:	159.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.525	Fsp³:	0.515
MCE-18:	102.0 ? 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:	0.921	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.059 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.187	Promiscuous compounds:	0.157

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.332	MDCK Permeability:	-4.76
Pgp-inhibitor:	1.0	Pgp-substrate:	0.026
PAMPA:	0.838 ? 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):	0.0
20% Bioavailability (F20%):	0.96	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	83.623%	Volume Distribution (VD):	-0.011
Fu:	17.049% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.668	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

4.58

Half-life (T1/2):

0.615

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.1
Human Hepatotoxicity (H-HT):	0.521	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.426	Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.213	Skin Sensitization:	0.988
Carcinogencity:	0.381	Eye Corrosion:	0.0
Eye Irritation:	0.061	Respiratory Toxicity:	0.058
Drug-induced Neurotoxicity:	0.274	Ototoxicity:	0.449
Hematotoxicity:	0.519	Drug-induced Nephrotoxicity:	0.929
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.228
A549 Cytotoxicity:	0.624	Hek293 Cytotoxicity:	0.374
BCF:	0.662 ? 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:	3.623 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.613 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.995 ? 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
NPO40845	Euphorbia glomerulans	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30860373]

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
Ratio IC50	1
IC50	3

Activity Type	# Activity
Cell line	2
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	4.9	n.a.	PMID[30860373]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	IC50	=	13300.0	nM	PMID[30860373]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]

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 NPC482302 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	7524
0.1-0.2	38307
0.2-0.3	3456
0.3-0.4	443
0.4-0.5	83
0.5-0.6	23
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC482310
0.8889	High Similarity	NPC482301
0.7368	Intermediate Similarity	NPC482308
0.7273	Intermediate Similarity	NPC482300
0.7273	Intermediate Similarity	NPC482315
0.7125	Intermediate Similarity	NPC482252
0.7013	Intermediate Similarity	NPC482313
0.6835	Remote Similarity	NPC86772
0.679	Remote Similarity	NPC205389
0.675	Remote Similarity	NPC475262
0.675	Remote Similarity	NPC482304
0.65	Remote Similarity	NPC482307
0.642	Remote Similarity	NPC482314
0.6341	Remote Similarity	NPC265459
0.6341	Remote Similarity	NPC482265
0.5952	Remote Similarity	NPC290833
0.5952	Remote Similarity	NPC482249
0.5698	Remote Similarity	NPC482347
0.5682	Remote Similarity	NPC482253
0.5652	Remote Similarity	NPC482258
0.5647	Remote Similarity	NPC276652
0.5542	Remote Similarity	NPC196683
0.5517	Remote Similarity	NPC482248
0.5455	Remote Similarity	NPC482268
0.5455	Remote Similarity	NPC482269
0.5455	Remote Similarity	NPC482272
0.5412	Remote Similarity	NPC473497
0.5412	Remote Similarity	NPC42234
0.5402	Remote Similarity	NPC82467
0.5402	Remote Similarity	NPC482270
0.5326	Remote Similarity	NPC482250
0.5281	Remote Similarity	NPC482267
0.5227	Remote Similarity	NPC272523
0.5172	Remote Similarity	NPC472250
0.5172	Remote Similarity	NPC325805
0.5063	Remote Similarity	NPC105725
0.5056	Remote Similarity	NPC482153
0.5053	Remote Similarity	NPC482353

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3505
0.1-0.2	5495
0.2-0.3	149
0.3-0.4	1
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