NPASS Compound

Natural Product: NPC53171

Natural Product ID	NPC53171
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UDSUNACNDRCFFJ-RUTAEVJPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	50994306
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 83 86 0 0 0 0 0 0 0 0999 V2000 -7.5858 -0.6953 2.0970 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8452 -0.7446 0.7907 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5597 -1.0567 0.7366 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7558 -1.1299 -0.4899 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2813 -0.8842 -0.2324 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0440 0.5057 0.3756 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5209 1.5912 -0.5182 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7428 0.6247 1.0314 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5412 1.9897 1.6153 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1072 2.3480 1.2512 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5263 0.9947 1.2216 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5362 0.4794 2.6298 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8185 0.9101 0.5447 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6872 1.8896 0.4158 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9989 1.7891 -0.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2723 0.4395 -0.8568 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6784 0.2019 -1.2431 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8136 -0.1341 -2.7360 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4892 1.4654 -1.0453 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2303 -0.9433 -0.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2803 -0.8074 0.0882 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4824 -2.2247 -0.5279 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9856 -2.0089 -0.5414 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6669 -0.6494 0.0375 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2821 -0.5519 1.3752 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1880 -0.4037 -0.0513 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3350 -1.5208 0.4975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1218 -1.2017 0.4306 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4834 0.2446 0.3331 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3491 0.6961 -1.0746 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 -2.4622 -0.9481 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2851 -2.5454 -2.2535 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6185 -0.4308 -0.4233 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8347 -0.8728 2.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0116 0.3260 2.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3592 -1.4759 2.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0703 -1.2736 1.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1266 -0.5193 -1.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7642 -1.0452 -1.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9563 -1.6664 0.4820 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8074 0.4864 1.2286 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5954 1.9001 -0.3138 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5997 1.2619 -1.6005 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9790 2.5277 -0.5451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7597 -0.0782 1.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6550 2.0057 2.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2579 2.7609 1.2982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0172 2.9323 0.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3327 2.8966 2.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0729 1.1860 3.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0620 -0.4856 2.7867 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6163 0.4867 2.9661 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4335 2.8451 0.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7846 2.1492 0.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9553 2.5402 -1.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6518 0.3831 -1.8017 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8552 -0.5622 -3.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0073 0.7804 -3.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6506 -0.8512 -2.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4409 1.3763 -1.6477 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9360 2.3002 -1.5218 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7233 1.6788 0.0019 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7555 -2.7254 -1.4991 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8150 -2.8754 0.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5322 -2.1710 -1.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5678 -2.7555 0.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0161 -1.3914 1.5694 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8822 0.3782 1.5285 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5886 -0.6133 2.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0085 -0.4274 -1.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6446 -1.8288 1.5193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5941 -2.4178 -0.1430 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6139 -1.7112 1.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -1.7855 -0.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2621 -0.1573 -1.8139 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2112 1.2639 -1.4838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5081 1.4211 -1.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3072 -2.1330 -2.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6298 -1.8405 -2.8466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1635 -3.5366 -2.6890 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4853 0.2159 -0.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0224 0.1215 -1.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0223 -1.3535 -0.8910 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 4 31 1 0 31 32 1 0 2 33 1 0 29 8 1 0 29 11 1 0 26 13 1 0 24 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 6 5 39 1 0 5 40 1 0 6 41 1 1 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 1 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 6 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 25 67 1 0 25 68 1 0 25 69 1 0 26 70 1 6 27 71 1 0 27 72 1 0 28 73 1 0 28 74 1 0 30 75 1 0 30 76 1 0 30 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 M END

Standard InCHIKey	UDSUNACNDRCFFJ-RUTAEVJPSA-N
Standard InCHI	InChI=1S/C31H50O2/c1-20(2)18-22(33-9)19-21(3)23-12-16-31(8)25-10-11-26-28(4,5)27(32)14-15-29(26,6)24(25)13-17-30(23,31)7/h10,18,21-24,26H,11-17,19H2,1-9H3/t21-,22-,23-,24-,26-,29+,30-,31+/m0/s1
SMILES	CC(=C[C@@H](C[C@H](C)[C@@H]1CC[C@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]12C)OC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.38	Volume:	520.177 ? Van der Waals volume.
Dense:	0.874	LogP:	6.723 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.514 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.172 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.392	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.895	Fsp³:	0.839
MCE-18:	79.719 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.874	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.682	Promiscuous compounds:	0.325

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.648	MDCK Permeability:	-4.686
Pgp-inhibitor:	0.995	Pgp-substrate:	0.0
PAMPA:	0.051 ? 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%):	0.02	30% Bioavailability (F30%):	0.008
50% Bioavailability (F50%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.59	MRP1:	0.922
Plasma Protein Binding (PPB):	94.124%	Volume Distribution (VD):	0.465
Fu:	6.311% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.76
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.956	CYP1A2-substrate:	0.92
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.449
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

10.846

Half-life (T1/2):

0.22

ADMET: Toxicity

hERG Blockers:	0.134	hERG Blockers (10um):	0.388
Human Hepatotoxicity (H-HT):	0.625	Drug-induced Liver Injury (DILI):	0.411
AMES Toxicity:	0.263	Rat Oral Acute Toxicity:	0.498
Maximum Recommended Daily Dose:	0.781	Skin Sensitization:	0.818
Carcinogencity:	0.852	Eye Corrosion:	0.01
Eye Irritation:	0.262	Respiratory Toxicity:	0.696
Drug-induced Neurotoxicity:	0.579	Ototoxicity:	0.476
Hematotoxicity:	0.675	Drug-induced Nephrotoxicity:	0.693
Genotoxicity:	0.734	RPMI-8226 Immunitoxicity:	0.12
A549 Cytotoxicity:	0.453	Hek293 Cytotoxicity:	0.603
BCF:	2.88 ? 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:	4.621 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.297 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.378 ? 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
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	stem	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19594	Cornus walteri	Species	Cornaceae	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 NPC53171 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	20365
0.1-0.2	25710
0.2-0.3	3369
0.3-0.4	304
0.4-0.5	61
0.5-0.6	21
0.6-0.7	20
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470047
1.0	High Similarity	NPC470046
0.7344	Intermediate Similarity	NPC470050
0.7344	Intermediate Similarity	NPC470051
0.7231	Intermediate Similarity	NPC605437
0.6984	Remote Similarity	NPC470052
0.6984	Remote Similarity	NPC470049
0.6885	Remote Similarity	NPC470078
0.6719	Remote Similarity	NPC90652
0.6719	Remote Similarity	NPC155255
0.6667	Remote Similarity	NPC486521
0.6667	Remote Similarity	NPC262870
0.6462	Remote Similarity	NPC260992
0.6406	Remote Similarity	NPC470223
0.6324	Remote Similarity	NPC67831
0.6324	Remote Similarity	NPC174051
0.6232	Remote Similarity	NPC479667
0.6176	Remote Similarity	NPC471224
0.6119	Remote Similarity	NPC470048
0.6087	Remote Similarity	NPC472239
0.6027	Remote Similarity	NPC63023
0.6027	Remote Similarity	NPC121566
0.6027	Remote Similarity	NPC100955
0.6027	Remote Similarity	NPC95243
0.6	Remote Similarity	NPC6190
0.5972	Remote Similarity	NPC73506
0.597	Remote Similarity	NPC470417
0.5915	Remote Similarity	NPC293081
0.5833	Remote Similarity	NPC273669
0.5833	Remote Similarity	NPC484802
0.5833	Remote Similarity	NPC118647
0.5758	Remote Similarity	NPC247220
0.5658	Remote Similarity	NPC189282
0.5658	Remote Similarity	NPC237402
0.5658	Remote Similarity	NPC484792
0.5493	Remote Similarity	NPC28227
0.5417	Remote Similarity	NPC484798
0.5362	Remote Similarity	NPC82902
0.5352	Remote Similarity	NPC147066
0.5205	Remote Similarity	NPC484789
0.5205	Remote Similarity	NPC484801
0.5205	Remote Similarity	NPC484786
0.5205	Remote Similarity	NPC484787
0.5205	Remote Similarity	NPC484788
0.5143	Remote Similarity	NPC474218
0.5135	Remote Similarity	NPC154101

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC53171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6685
0.1-0.2	2385
0.2-0.3	79
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