NPASS Compound

Natural Product: NPC469599

Natural Product ID	NPC469599
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(25R)-26-Hydroxy-22-Oxocholest-5-En-3Beta,16Beta-Diyldiacetate
IUPAC Name	[(3S,8S,9S,10R,13S,14S,16S,17R)-16-acetyloxy-17-[(2S,6R)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1093269
PubChem CID	14769377
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000260] Monohydroxy bile acids, alcohols 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 85 88 0 0 0 0 0 0 0 0999 V2000 -8.9991 0.6078 -1.9999 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4004 1.6450 -1.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2020 1.1132 -0.5248 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1687 0.5482 -1.4775 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9626 0.0176 -0.6752 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9396 -0.5357 -1.5578 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2102 -0.3703 -2.7875 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6867 -1.2360 -1.2029 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7263 -0.4859 -0.4543 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1179 -0.0280 0.9138 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8854 -0.9618 1.6524 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9366 -0.6381 2.4638 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2818 0.5536 2.6042 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7251 -1.6526 3.2182 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7596 0.1565 1.6787 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1973 0.2017 0.5512 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3286 -0.9873 -0.2830 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1974 -2.1966 0.5689 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5264 -0.9650 -1.5055 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9667 -1.2824 -1.1361 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4859 -0.1751 -0.2572 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6292 0.0941 0.9306 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0345 1.4804 1.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5015 1.6505 1.4295 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3732 0.8235 0.8722 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8936 -0.3959 0.1807 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8984 -1.5730 1.1640 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8050 -0.7985 -0.9578 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2310 -0.7468 -0.5239 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5835 0.6773 -0.2166 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8121 1.1833 0.9829 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9467 0.9199 -0.0621 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6853 1.7825 -0.8574 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0716 2.3837 -1.7808 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1405 2.0289 -0.6776 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2598 -2.0144 -2.4120 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6226 2.2367 0.3042 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8563 0.3332 -1.5979 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1359 2.4643 -1.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1738 2.0430 -0.5951 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5518 0.3306 0.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6446 -0.2827 -2.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8829 1.3468 -2.1661 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6154 0.8426 -0.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3698 -0.7740 -0.0184 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0713 -2.0715 -0.4947 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5578 0.5156 -1.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5618 0.9556 1.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1697 -2.5768 3.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6766 -1.8415 2.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9791 -1.2086 4.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7931 1.0384 2.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6711 -0.7187 2.3323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0494 1.1541 0.0009 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1634 -2.4787 1.0790 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1746 -3.0713 -0.0421 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5371 -2.1126 1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2713 -1.6409 -2.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5290 0.0676 -1.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5449 -1.2356 -2.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0923 -2.2829 -0.7206 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4759 0.7556 -0.8893 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8248 -0.5865 1.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6071 2.2561 0.7426 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6141 1.6655 2.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8703 2.5602 1.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7149 -2.2996 0.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1301 -1.2103 2.2063 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9508 -2.1483 1.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5279 -1.8458 -1.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6918 -0.1621 -1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4542 -1.3971 0.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8864 -1.0906 -1.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2250 1.3016 -1.0865 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9559 2.2773 1.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1769 0.7622 1.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6180 2.1003 -1.6899 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6112 1.2639 -0.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2401 3.0482 -0.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8904 -1.3433 -3.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2335 -2.4035 -2.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -2.9168 -2.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3938 3.0240 0.4970 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3369 1.8519 1.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7228 2.6798 -0.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 10 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 8 36 1 0 3 37 1 0 17 9 1 0 26 21 1 0 22 16 1 0 31 25 1 0 1 38 1 0 2 39 1 0 2 40 1 0 3 41 1 1 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 8 46 1 1 9 47 1 6 10 48 1 6 14 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 6 18 55 1 0 18 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 6 22 63 1 1 23 64 1 0 23 65 1 0 24 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 30 74 1 6 31 75 1 0 31 76 1 0 35 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 M END

Standard InCHIKey	INUVWOFKWFJJFJ-WLMGVJRSSA-N
Standard InCHI	InChI=1S/C31H48O6/c1-18(17-32)7-10-27(35)19(2)29-28(37-21(4)34)16-26-24-9-8-22-15-23(36-20(3)33)11-13-30(22,5)25(24)12-14-31(26,29)6/h8,18-19,23-26,28-29,32H,7,9-17H2,1-6H3/t18-,19-,23+,24-,25+,26+,28+,29+,30+,31+/m1/s1
SMILES	OC[C@@H](CCC(=O)[C@H]([C@H]1[C@@H](OC(=O)C)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)OC(=O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.35	Volume:	552.702 ? Van der Waals volume.
Dense:	0.934	LogP:	3.923 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.575 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.474 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	23.0
TPSA:	89.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.331	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.875	Fsp³:	0.839
MCE-18:	75.789 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.861	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.331	Promiscuous compounds:	0.839

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.377	MDCK Permeability:	-5.145
Pgp-inhibitor:	0.979	Pgp-substrate:	0.045
PAMPA:	0.825 ? 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%):	0.082	30% Bioavailability (F30%):	0.399
50% Bioavailability (F50%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.889
Plasma Protein Binding (PPB):	82.049%	Volume Distribution (VD):	-0.056
Fu:	14.744% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.737
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.002 ? 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):

7.688

Half-life (T1/2):

0.42

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.039
Human Hepatotoxicity (H-HT):	0.49	Drug-induced Liver Injury (DILI):	0.504
AMES Toxicity:	0.53	Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.193	Skin Sensitization:	0.995
Carcinogencity:	0.898	Eye Corrosion:	0.031
Eye Irritation:	0.689	Respiratory Toxicity:	0.289
Drug-induced Neurotoxicity:	0.04	Ototoxicity:	0.319
Hematotoxicity:	0.753	Drug-induced Nephrotoxicity:	0.886
Genotoxicity:	0.393	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.788	Hek293 Cytotoxicity:	0.391
BCF:	0.619 ? 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:	3.496 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.316 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.557 ? 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
NPO33234	chamaellirium luteum	Species	n.a.	n.a.	roots	sourced from Botanical Liaisons Ltd. (USA) and Blessed Herbs Ltd. (USA)	n.a.	PMID[22880631]
NPO33234	chamaellirium luteum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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	8
Activity	2

Activity Type	# Activity
Cell line	10

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
NPT2306	Cell line	Ca-Ski	Homo sapiens	IC50	=	47100.0	nM	PMID[17958396]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	76.15	%	PMID[20307086]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	23.85	%	PubChem BioAssay data set
NPT2306	Cell line	Ca-Ski	Homo sapiens	IC50	=	33900.0	nM	PMID[15104495]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[24224794]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[24224794]
NPT1524	Cell line	MM96L	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[19995673]
NPT111	Cell line	K562	Homo sapiens	IC50	=	1.7	ug.mL-1	PMID[21345685]
NPT1523	Cell line	NFF	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[12608855]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	2.8	ug.mL-1	PMID[16499319]

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 NPC469599 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	19064
0.1-0.2	24866
0.2-0.3	5577
0.3-0.4	296
0.4-0.5	48
0.5-0.6	5
0.6-0.7	2
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
0.6301	Remote Similarity	NPC470613
0.6301	Remote Similarity	NPC470612
0.5714	Remote Similarity	NPC100451
0.5641	Remote Similarity	NPC485606
0.5571	Remote Similarity	NPC153987
0.5493	Remote Similarity	NPC44083
0.5441	Remote Similarity	NPC609635

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6692
0.1-0.2	2239
0.2-0.3	197
0.3-0.4	19
0.4-0.5	3
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