NPASS Compound

Natural Product: NPC309603

Natural Product ID	NPC309603
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6Beta-Hydroxy-24-Ethylcholesta-4,24(28)-Dien-3-One
IUPAC Name	(6R,8S,9S,10R,13R,14S,17R)-6-hydroxy-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL485978
PubChem CID	10717343
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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 77 80 0 0 0 0 0 0 0 0999 V2000 4.8936 3.4546 0.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4934 2.2422 0.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1646 1.0069 0.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1377 0.7824 -0.7870 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9531 -0.0292 -0.2313 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9946 -0.1848 -1.3460 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7256 -0.9291 -2.4742 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7384 -0.8598 -1.1087 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8196 -2.2938 -0.6348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5470 -2.5814 0.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3095 -1.3528 -0.3047 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5482 -1.0759 0.4132 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5925 -2.0939 0.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5881 -1.5936 -0.9806 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2582 -0.4036 -0.4282 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5436 -0.1706 -0.5664 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1230 1.0437 0.0183 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3120 1.0546 0.3927 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2840 2.2366 0.1537 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8319 1.9425 -0.1814 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4125 0.5844 0.3268 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6714 0.4428 1.8119 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0015 0.3251 -0.0476 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9849 1.2997 0.4188 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7290 1.0722 -0.4386 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2219 -0.2802 -0.1179 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2417 -0.3852 1.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4851 -2.6395 -1.2182 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8324 -0.1555 0.8644 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5655 -1.0027 -0.1672 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8649 0.2623 1.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5077 4.3272 0.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8665 3.6607 0.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8772 3.4764 -1.1025 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2649 2.3306 1.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7859 1.7584 -1.1725 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5393 0.2422 -1.6946 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5821 0.5876 0.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3792 -0.9857 0.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7897 0.8281 -1.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0427 -1.6265 -2.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2130 -0.2175 -3.1725 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5200 -1.5525 -2.0190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1762 -0.9104 -2.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9193 -3.0024 -1.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6482 -2.4977 0.0389 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4143 -2.7297 1.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0190 -3.4777 -0.4460 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5285 -1.3642 -1.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5036 -1.0672 1.5063 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1785 -2.4474 0.9054 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1381 -3.0155 -0.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1270 -1.3719 -1.9678 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1691 -0.8697 -1.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6259 2.9659 -0.6345 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3589 2.7146 1.1314 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7307 1.8929 -1.3044 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2137 2.7744 0.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6929 0.4195 2.3291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2850 1.3039 2.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2717 -0.4773 1.9996 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9567 0.3053 -1.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6604 1.0247 1.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2640 2.3473 0.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9463 1.2089 -1.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0147 1.8342 -0.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5464 -0.8124 1.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4812 0.6085 1.7632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1019 -1.1078 1.4269 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9563 -3.3266 -1.7340 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1133 -0.8150 1.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3363 -1.5746 0.3868 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0965 -0.3522 -0.8845 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8946 -1.7384 -0.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4451 0.8355 2.7240 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6750 0.8551 1.3904 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3654 -0.6801 2.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 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 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 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 1 14 28 1 0 3 29 1 0 29 30 1 0 29 31 1 0 26 8 1 0 26 11 1 0 23 12 1 0 21 15 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 6 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 6 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 6 12 50 1 1 13 51 1 0 13 52 1 0 14 53 1 6 16 54 1 0 19 55 1 0 19 56 1 0 20 57 1 0 20 58 1 0 22 59 1 0 22 60 1 0 22 61 1 0 23 62 1 6 24 63 1 0 24 64 1 0 25 65 1 0 25 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 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 31 77 1 0 M END

Standard InCHIKey	PRKRLDJHSWQHED-CLUHYBOGSA-N
Standard InCHI	InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h7,16,18-19,22-25,27,31H,8-15,17H2,1-6H3/b20-7+/t19-,22+,23-,24+,25+,27-,28-,29-/m1/s1
SMILES	C/C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)O)/C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.35	Volume:	485.585 ? Van der Waals volume.
Dense:	0.878	LogP:	6.556 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.708 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.195 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.475	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.657	Fsp³:	0.828
MCE-18:	70.792 ? 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:	0.902	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.422	Promiscuous compounds:	0.297

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.001	MDCK Permeability:	-5.027
Pgp-inhibitor:	0.788	Pgp-substrate:	0.0
PAMPA:	0.004 ? 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%):	0.469	30% Bioavailability (F30%):	0.968
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.043
Plasma Protein Binding (PPB):	97.249%	Volume Distribution (VD):	0.046
Fu:	3.351% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.641
BSEP inhibitor:	0.937

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.78
CYP2C19-inhibitor:	0.818	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.214
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.991
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.83 ? 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):

10.571

Half-life (T1/2):

0.563

ADMET: Toxicity

hERG Blockers:	0.139	hERG Blockers (10um):	0.422
Human Hepatotoxicity (H-HT):	0.654	Drug-induced Liver Injury (DILI):	0.21
AMES Toxicity:	0.097	Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.585	Skin Sensitization:	0.704
Carcinogencity:	0.533	Eye Corrosion:	0.04
Eye Irritation:	0.847	Respiratory Toxicity:	0.702
Drug-induced Neurotoxicity:	0.18	Ototoxicity:	0.571
Hematotoxicity:	0.508	Drug-induced Nephrotoxicity:	0.614
Genotoxicity:	0.224	RPMI-8226 Immunitoxicity:	0.095
A549 Cytotoxicity:	0.096	Hek293 Cytotoxicity:	0.392
BCF:	2.629 ? 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:	4.558 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.644 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.385 ? 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
NPO16318	Turbinaria conoides	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075746]
NPO16318	Turbinaria conoides	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15720	Russula flavida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6567	Aesculus x carnea	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15720	Russula flavida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20447	Ichthyothere rufa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18754	Agathosma capensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27825	Diospyros sapota	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16768	Tortella inclinata	Species	Pottiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6567	Aesculus x carnea	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21457	Schefflera taiwaniana	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16318	Turbinaria conoides	Species	Sargassaceae	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
ED50	4

Activity Type	# Activity
Cell line	4

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
NPT168	Cell line	P388	Mus musculus	ED50	=	0.9	ug ml-1	PMID[10075746]
NPT91	Cell line	KB	Homo sapiens	ED50	=	4.6	ug ml-1	PMID[10075746]
NPT81	Cell line	A549	Homo sapiens	ED50	=	2.3	ug ml-1	PMID[10075746]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[10075746]

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 NPC309603 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	15235
0.1-0.2	29309
0.2-0.3	4960
0.3-0.4	293
0.4-0.5	38
0.5-0.6	9
0.6-0.7	4
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
0.7818	Intermediate Similarity	NPC473999
0.7167	Intermediate Similarity	NPC473998
0.7119	Intermediate Similarity	NPC475806
0.7049	Intermediate Similarity	NPC489873
0.6909	Remote Similarity	NPC282593
0.6667	Remote Similarity	NPC8993
0.6552	Remote Similarity	NPC303613
0.6207	Remote Similarity	NPC159577
0.5738	Remote Similarity	NPC209430
0.5667	Remote Similarity	NPC35734
0.5667	Remote Similarity	NPC602429
0.5574	Remote Similarity	NPC149203
0.55	Remote Similarity	NPC214043
0.55	Remote Similarity	NPC85774
0.5079	Remote Similarity	NPC237712
0.5077	Remote Similarity	NPC469948
0.5075	Remote Similarity	NPC320514

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC309603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5937
0.1-0.2	2899
0.2-0.3	237
0.3-0.4	66
0.4-0.5	10
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