NPASS Compound

Natural Product: NPC476973

Natural Product ID	NPC476973
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(1S,2S,5S,6S,7S,9R,12R)-5-acetyloxy-6-(acetyloxymethyl)-2,12-dihydroxy-2,10-dimethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-10-yl]methyl benzoate
IUPAC Name	[(1S,2S,5S,6S,7S,9R,12R)-5-acetyloxy-6-(acetyloxymethyl)-2,12-dihydroxy-2,10-dimethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-10-yl]methyl benzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	118726319
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 86 90 0 0 0 0 0 0 0 0999 V2000 -2.3440 -5.5301 -2.4770 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2487 -4.0505 -2.3970 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0686 -3.3631 -3.0593 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2690 -3.4710 -1.6028 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2086 -2.1015 -1.5515 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1322 -1.4871 -0.6788 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3636 -1.9819 0.6989 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0634 -3.4461 0.8627 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9554 -4.0925 0.0568 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5531 -3.3531 -1.0918 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2786 -1.8947 -0.9967 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7403 -1.0586 -2.1065 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1861 0.1802 -1.2894 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9324 0.8319 -0.8553 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2971 -0.0313 -0.9169 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2836 0.5020 -0.0583 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4281 1.1319 -0.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5446 1.1874 -1.7894 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4561 1.7098 0.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5330 2.2950 -0.1349 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5827 2.8842 0.6805 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6613 3.4664 0.0231 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7089 4.0524 0.7017 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7196 4.0796 2.0716 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6576 3.5066 2.7295 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5971 2.9133 2.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8503 -0.4894 -0.1535 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0145 -1.5213 0.1702 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2673 -0.9392 -0.4684 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0101 0.3629 1.0869 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8319 1.4941 0.8200 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1089 2.4080 1.8215 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6013 2.1780 2.9471 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9386 3.5817 1.6161 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5233 3.8903 0.4083 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3127 5.0278 0.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5217 5.8745 1.3345 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9464 5.5752 2.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1573 4.4328 2.6732 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6961 -1.5549 -2.9279 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3599 -3.9815 -2.4373 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9694 -3.4558 -0.8817 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7348 -1.7917 1.0507 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1752 -1.0662 2.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3628 -0.5010 2.8697 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6594 -1.0027 2.3300 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5794 -5.8797 -1.4358 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0949 -5.8466 -3.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3240 -5.9005 -2.7399 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2246 -1.6045 -2.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1741 -1.7470 -1.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2343 -1.4044 1.4207 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0596 -3.9773 0.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1235 -3.5682 1.9732 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7456 -4.5088 0.7612 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5564 -5.0626 -0.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9245 -0.6551 -2.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8488 0.8155 -1.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 1.3555 0.1054 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7940 1.6986 -1.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7010 0.1741 -1.9656 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3423 1.6740 1.4166 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6141 2.3239 -1.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7226 3.4833 -1.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5507 4.5067 0.1804 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5572 4.5476 2.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6574 3.5236 3.8186 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7854 2.4760 2.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5883 -1.6175 0.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4550 -1.2471 -1.4825 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9099 -0.0163 -0.3210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 0.7080 1.4611 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5997 -0.1991 1.8677 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3906 3.2663 -0.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7804 5.2850 -0.6888 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1341 6.7612 1.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0977 6.2216 3.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7350 4.2648 3.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5745 -1.3519 -3.8727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8989 -3.3240 -3.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8560 -4.9746 -2.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3353 -4.2779 -2.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2504 -4.4008 -1.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1876 -0.9010 1.3780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0281 -1.9239 2.8340 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8644 -0.0976 2.9489 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 4 5 1 0 6 5 1 6 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 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 13 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 30 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 12 40 1 0 10 41 1 0 10 42 1 1 7 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 11 6 1 0 15 6 1 0 11 28 1 1 26 21 1 0 39 34 1 0 1 47 1 0 1 48 1 0 1 49 1 0 5 50 1 0 5 51 1 0 7 52 1 1 8 53 1 0 8 54 1 0 9 55 1 0 9 56 1 0 12 57 1 6 13 58 1 6 14 59 1 0 14 60 1 0 15 61 1 6 19 62 1 0 20 63 1 0 22 64 1 0 23 65 1 0 24 66 1 0 25 67 1 0 26 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 35 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 39 78 1 0 40 79 1 0 41 80 1 0 41 81 1 0 41 82 1 0 42 83 1 0 46 84 1 0 46 85 1 0 46 86 1 0 M END

Standard InCHIKey	CFCWERMAAXCFKA-OWYAAZHBSA-N
Standard InCHI	InChI=1S/C35H40O11/c1-22(36)42-21-34-27(44-23(2)37)17-18-33(4,41)35(34)30(39)26(19-28(34)45-29(38)16-15-24-11-7-5-8-12-24)32(3,46-35)20-43-31(40)25-13-9-6-10-14-25/h5-16,26-28,30,39,41H,17-21H2,1-4H3/b16-15+/t26-,27+,28+,30-,32?,33+,34+,35+/m1/s1
SMILES	CC(=O)OC[C@@]12[C@H](CC[C@]([C@@]13[C@@H]([C@@H](C[C@@H]2OC(=O)/C=C/C4=CC=CC=C4)C(O3)(C)COC(=O)C5=CC=CC=C5)O)(C)O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.26	Volume:	638.825 ? Van der Waals volume.
Dense:	0.996	LogP:	3.8 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.194 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.655 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	31.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.236	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.966	Fsp³:	0.486
MCE-18:	163.654 ? 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:	0.91	Fluc inhibitor:	0.434 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.526 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.039	Promiscuous compounds:	0.117

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.582	MDCK Permeability:	-4.936
Pgp-inhibitor:	0.999	Pgp-substrate:	0.041
PAMPA:	0.141 ? 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%):	0.305	30% Bioavailability (F30%):	0.905
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246	MRP1:	0.996
Plasma Protein Binding (PPB):	95.195%	Volume Distribution (VD):	-0.607
Fu:	6.223% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.012
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.328
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.774
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.841 ? 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):

4.232

Half-life (T1/2):

0.888

ADMET: Toxicity

hERG Blockers:	0.184	hERG Blockers (10um):	0.445
Human Hepatotoxicity (H-HT):	0.175	Drug-induced Liver Injury (DILI):	0.735
AMES Toxicity:	0.771	Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.945	Skin Sensitization:	0.998
Carcinogencity:	0.889	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.035
Drug-induced Neurotoxicity:	0.541	Ototoxicity:	0.26
Hematotoxicity:	0.012	Drug-induced Nephrotoxicity:	0.838
Genotoxicity:	0.845	RPMI-8226 Immunitoxicity:	0.194
A549 Cytotoxicity:	0.206	Hek293 Cytotoxicity:	0.672
BCF:	0.634 ? 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:	3.595 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.332 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.848 ? 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
NPO33650	Denhamia celastroides	Species	Celastraceae	Eukaryota	leave	Walton Bridge Reserve, The Gap, Australia	2012-OCT	PMID[25579619]

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
IC50	1

Activity Type	# Activity
Cell line	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
NPT858	Cell line	LNCaP	Homo sapiens	IC50	>	10000	nM	PMID[25579619]

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 NPC476973 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	10837
0.1-0.2	34772
0.2-0.3	3695
0.3-0.4	463
0.4-0.5	70
0.5-0.6	18
0.6-0.7	1
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
0.7821	Intermediate Similarity	NPC476972
0.75	Intermediate Similarity	NPC476974
0.6235	Remote Similarity	NPC476970
0.5895	Remote Similarity	NPC96801
0.5895	Remote Similarity	NPC150698
0.5729	Remote Similarity	NPC476975
0.5729	Remote Similarity	NPC476977
0.5714	Remote Similarity	NPC294579
0.5714	Remote Similarity	NPC144779
0.5667	Remote Similarity	NPC476971
0.5604	Remote Similarity	NPC70403
0.5604	Remote Similarity	NPC177940
0.5275	Remote Similarity	NPC488915
0.5213	Remote Similarity	NPC174982
0.5158	Remote Similarity	NPC171525
0.5057	Remote Similarity	NPC470158
0.5056	Remote Similarity	NPC171207
0.5054	Remote Similarity	NPC488920
0.5053	Remote Similarity	NPC125106
0.5053	Remote Similarity	NPC472573
0.5049	Remote Similarity	NPC6981

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3942
0.1-0.2	5055
0.2-0.3	153
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