NPASS Compound

Natural Product: NPC137306

Natural Product ID	NPC137306
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Acetyldaturadiol
IUPAC Name	[(3S,4aR,5R,6aR,6bS,8aR,12aR,14aR,14bR)-5-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] acetate
Synonyms	3-O-Acetyldaturadiol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL515444
PubChem CID	21672207
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 87 91 0 0 0 0 0 0 0 0999 V2000 8.5564 0.7517 1.6329 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0859 0.8123 1.8019 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5225 0.9507 2.9063 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2798 0.7133 0.7008 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8819 0.7530 0.6996 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3012 1.9746 0.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8081 1.9209 0.1620 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2212 0.6984 -0.5577 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8110 -0.5124 0.1033 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2847 -0.5490 0.2735 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5510 -1.5037 1.4697 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0378 -1.2436 -0.8227 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2494 -1.7635 -0.4894 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7209 -2.0457 -1.7675 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7520 -1.8240 -0.3848 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0223 -0.5557 -0.6372 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7571 0.6784 -0.1720 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0244 1.8850 -0.4945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4627 1.6409 -0.7027 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0949 0.5001 -0.4082 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2905 -0.5801 0.1631 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0402 -0.1983 1.6294 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9748 -1.8844 0.1529 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0758 -2.0579 -0.8269 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1164 -0.9349 -0.7890 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5733 0.4136 -0.6786 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1905 1.3460 0.3237 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5497 0.9869 0.7964 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8405 1.8627 2.0233 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6545 1.2080 -0.1667 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4324 -0.4204 1.3153 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1655 -1.3535 0.1900 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7940 -1.0573 -2.1773 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3662 -0.3412 -2.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4914 0.8588 -1.9922 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9719 1.7123 1.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9851 -0.0300 2.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8628 0.4725 0.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6046 0.8783 1.7945 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6045 2.8482 0.7168 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7045 2.2252 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3330 2.8528 -0.1998 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5520 1.7810 1.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3886 -0.4827 1.1604 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3723 -2.5411 1.2038 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0066 -1.1140 2.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6502 -1.3436 1.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8378 -0.9445 -1.8348 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8106 -2.3499 -0.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1254 -1.1893 -0.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6388 -2.6171 0.1452 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0003 -2.5720 -2.2222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4153 -2.5958 -1.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5152 -2.1275 0.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7917 0.5914 0.9581 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3342 2.4657 -1.3782 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0459 2.6274 0.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0549 2.4530 -1.1290 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9750 -0.5508 2.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2263 -0.7611 2.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0382 0.8874 1.7819 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4201 -2.1193 1.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2861 -2.7646 -0.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7417 -2.2871 -1.8684 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5936 -3.0246 -0.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6677 0.9774 -1.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5462 1.4141 1.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2306 2.4170 -0.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9225 1.6854 2.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1809 1.5965 2.8621 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7570 2.9131 1.6973 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2101 0.2548 -0.3317 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4222 1.9439 0.1868 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2936 1.5112 -1.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6339 -0.4520 2.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3745 -0.7142 1.8002 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9298 -2.3510 0.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1741 -1.5612 -0.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8383 -0.7401 -2.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2227 -0.4696 -2.9268 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7832 -2.1032 -2.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0521 0.6750 -2.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4857 -0.2933 -2.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0246 -1.1568 -2.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0281 1.8406 -2.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5770 1.0565 -2.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2409 0.0461 -2.6646 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 9 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 2 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 31 32 1 0 25 33 1 6 16 34 1 6 8 35 1 6 10 5 1 0 21 16 1 0 32 25 1 0 17 8 1 0 26 20 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 1 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 9 44 1 1 11 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 1 14 52 1 0 15 53 1 0 15 54 1 0 17 55 1 1 18 56 1 0 18 57 1 0 19 58 1 0 22 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 26 66 1 6 27 67 1 0 27 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 32 77 1 0 32 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 35 85 1 0 35 86 1 0 35 87 1 0 M END

Standard InCHIKey	KHNOTTSLMUNERG-FNTGSRHESA-N
Standard InCHI	InChI=1S/C32H52O3/c1-20(33)35-25-12-13-30(7)24-11-10-21-22-18-27(2,3)14-15-29(22,6)16-17-31(21,8)32(24,9)19-23(34)26(30)28(25,4)5/h10,22-26,34H,11-19H2,1-9H3/t22-,23+,24+,25-,26-,29+,30+,31+,32+/m0/s1
SMILES	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)[C@H](O)C[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	484.39	Volume:	540.343 ? Van der Waals volume.
Dense:	0.896	LogP:	3.773 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.597 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.792 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.306	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.834	Fsp³:	0.906
MCE-18:	106.23 ? 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:	0.947	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.064 ? 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:	0.359	Promiscuous compounds:	0.341

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.837	MDCK Permeability:	-4.724
Pgp-inhibitor:	1.0	Pgp-substrate:	0.004
PAMPA:	0.144 ? 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):	0.002
20% Bioavailability (F20%):	0.994	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.842	MRP1:	0.889
Plasma Protein Binding (PPB):	96.426%	Volume Distribution (VD):	0.051
Fu:	4.26% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.452
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.992	CYP2C19-substrate:	0.26
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	1.0	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):

9.506

Half-life (T1/2):

0.344

ADMET: Toxicity

hERG Blockers:	0.064	hERG Blockers (10um):	0.339
Human Hepatotoxicity (H-HT):	0.512	Drug-induced Liver Injury (DILI):	0.316
AMES Toxicity:	0.115	Rat Oral Acute Toxicity:	0.36
Maximum Recommended Daily Dose:	0.468	Skin Sensitization:	0.765
Carcinogencity:	0.709	Eye Corrosion:	0.028
Eye Irritation:	0.362	Respiratory Toxicity:	0.336
Drug-induced Neurotoxicity:	0.055	Ototoxicity:	0.384
Hematotoxicity:	0.373	Drug-induced Nephrotoxicity:	0.36
Genotoxicity:	0.314	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.261	Hek293 Cytotoxicity:	0.482
BCF:	2.668 ? 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:	4.706 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.126 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.831 ? 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
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10543897]
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

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
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	>	1250.0	ug.mL-1	PubChem BioAssay data set
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	78.0	ug.mL-1	PMID[25798528]

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 NPC137306 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	18046
0.1-0.2	25124
0.2-0.3	5770
0.3-0.4	817
0.4-0.5	77
0.5-0.6	17
0.6-0.7	5
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
0.7049	Intermediate Similarity	NPC195334
0.6269	Remote Similarity	NPC191965
0.6154	Remote Similarity	NPC224145
0.6056	Remote Similarity	NPC260149
0.6029	Remote Similarity	NPC10005
0.6029	Remote Similarity	NPC91525
0.5942	Remote Similarity	NPC286786
0.5882	Remote Similarity	NPC162107
0.5882	Remote Similarity	NPC46912
0.5867	Remote Similarity	NPC327179
0.5753	Remote Similarity	NPC488520
0.5417	Remote Similarity	NPC23621
0.5385	Remote Similarity	NPC290598
0.5385	Remote Similarity	NPC30590
0.5362	Remote Similarity	NPC480944
0.5294	Remote Similarity	NPC290495
0.5294	Remote Similarity	NPC475862
0.5217	Remote Similarity	NPC470588
0.5195	Remote Similarity	NPC86368
0.5195	Remote Similarity	NPC488522
0.5072	Remote Similarity	NPC478657
0.507	Remote Similarity	NPC84121
0.5063	Remote Similarity	NPC488524

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC137306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6635
0.1-0.2	2436
0.2-0.3	74
0.3-0.4	4
0.4-0.5	1
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