NPASS Compound

Natural Product: NPC485424

Natural Product ID	NPC485424
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YLEXRPOVNWIAJQ-PEBRZITQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 97102 0 0 0 0 0 0 0 0999 V2000 -6.6056 0.2395 -2.8883 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5955 -0.6446 -1.6375 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6051 -1.7568 -1.9807 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2652 0.1679 -0.5620 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9038 -0.4569 0.7542 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4324 -0.2820 1.0430 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0611 1.1435 1.3904 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6097 1.1002 1.7109 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7336 0.4590 0.9155 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2904 0.4683 1.3229 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1992 -0.2026 2.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8514 1.9182 1.5313 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6636 1.9556 1.7650 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2859 1.3703 0.5513 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6978 1.7602 0.3499 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7298 3.2977 0.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6669 1.2559 1.3723 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1829 1.4363 -1.0482 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1839 0.5201 -1.7581 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6311 -0.5101 -0.8763 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7149 -1.6724 -1.2063 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9832 -0.1032 0.3997 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5136 -0.9843 1.4651 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5013 -0.1593 0.2115 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0971 -1.4769 -0.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3595 -1.2191 -0.8964 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2676 -0.1769 -0.2857 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3999 0.9068 -1.3464 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6065 -0.8721 -0.0343 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3022 -1.2373 -1.3075 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4586 0.8002 -0.9274 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5828 1.2909 -1.5690 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4129 2.3249 -2.2619 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9043 0.6790 -1.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1580 -0.3966 -0.7714 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4604 -1.0458 -0.6457 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5847 -0.5885 -1.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7827 -1.2559 -1.1022 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8485 -2.3763 -0.2993 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7104 -2.8402 0.3389 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5437 -2.1635 0.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0513 -3.0588 -0.1162 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2595 -1.0093 2.3674 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4877 -1.9803 2.4849 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9917 -0.5506 3.4340 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4687 1.3156 -2.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6540 0.2370 -3.2936 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8824 -0.0771 -3.6401 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4040 -2.6173 -1.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3523 -2.0559 -3.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6325 -1.3859 -1.8919 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9890 1.2424 -0.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3803 0.1401 -0.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0519 -1.5671 0.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5557 -0.1658 1.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3746 1.9006 0.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6088 1.3666 2.3490 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2541 1.6000 2.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1817 -0.0201 3.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1244 -1.3093 2.6219 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4555 0.2230 3.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3010 2.3333 2.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0273 2.5044 0.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9679 1.5314 2.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9370 3.0507 1.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7296 1.8457 -0.3210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9098 3.6051 1.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6313 3.6226 -0.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8505 3.7560 -0.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5159 2.0026 1.4315 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2734 1.1779 2.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1925 0.3189 1.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2577 2.3357 -1.6966 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3872 1.1938 -2.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7268 0.1068 -2.6289 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8777 -1.9220 1.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6254 -0.5575 2.4598 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5330 -1.3966 1.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6872 0.5028 -0.6909 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4936 -2.1581 -0.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4027 -2.0908 0.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0046 -0.9591 -1.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8792 -2.1907 -1.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7101 1.7207 -1.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0173 0.5799 -2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3941 1.3562 -1.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2581 -1.8707 0.4038 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3773 -2.3528 -1.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5919 -0.9767 -2.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7162 1.1380 -2.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3207 -0.8240 -0.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5291 0.3040 -1.9153 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6813 -0.9031 -1.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7739 -3.7377 0.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6536 -2.5557 0.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8457 -2.5899 0.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7480 -0.8023 4.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 18 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 39 40 1 0 40 41 2 0 39 42 1 0 6 43 1 1 43 44 2 0 43 45 1 0 30 2 1 0 41 36 1 0 29 6 1 0 27 9 1 0 24 10 1 0 22 14 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 11 59 1 0 11 60 1 0 11 61 1 0 12 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 14 66 1 6 16 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 17 72 1 0 18 73 1 6 19 74 1 0 19 75 1 0 23 76 1 0 23 77 1 0 23 78 1 0 24 79 1 6 25 80 1 0 25 81 1 0 26 82 1 0 26 83 1 0 28 84 1 0 28 85 1 0 28 86 1 0 29 87 1 1 30 88 1 0 30 89 1 0 34 90 1 0 35 91 1 0 37 92 1 0 38 93 1 0 40 94 1 0 41 95 1 0 42 96 1 0 45 97 1 0 M END

Standard InCHIKey	YLEXRPOVNWIAJQ-PEBRZITQSA-N
Standard InCHI	InChI=1S/C39H52O6/c1-34(2)20-21-39(33(43)44)19-16-27-36(5)17-14-26-35(3,4)31(45-32(42)13-10-24-8-11-25(40)12-9-24)22-30(41)38(26,7)28(36)15-18-37(27,6)29(39)23-34/h8-13,16,26,28-29,31,40H,14-15,17-23H2,1-7H3,(H,43,44)/b13-10+/t26-,28-,29-,31-,36-,37+,38-,39+/m0/s1
SMILES	CC1(C)CC[C@@]2(CC=C3[C@]4(C)CC[C@H]5C(C)(C)[C@H](CC(=O)[C@]5(C)[C@H]4CC[C@@]3(C)[C@@H]2C1)OC(=O)/C=C/c1ccc(cc1)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	616.38	Volume:	663.411 ? Van der Waals volume.
Dense:	0.929	LogP:	4.205 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.399 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.73 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	36.0
TPSA:	100.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.2	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.137	Fsp³:	0.667
MCE-18:	164.892 ? 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:	0.985	Fluc inhibitor:	0.747 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.04 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.22 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.262	Promiscuous compounds:	0.05

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.297	MDCK Permeability:	-5.036
Pgp-inhibitor:	0.999	Pgp-substrate:	0.0
PAMPA:	0.578 ? 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):	0.001
20% Bioavailability (F20%):	0.73	30% Bioavailability (F30%):	0.866
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.046
Plasma Protein Binding (PPB):	95.272%	Volume Distribution (VD):	-0.04
Fu:	3.858% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.141
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.122	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.128	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.032 ? 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):

1.003

Half-life (T1/2):

1.683

ADMET: Toxicity

hERG Blockers:	0.178	hERG Blockers (10um):	0.192
Human Hepatotoxicity (H-HT):	0.694	Drug-induced Liver Injury (DILI):	0.78
AMES Toxicity:	0.209	Rat Oral Acute Toxicity:	0.26
Maximum Recommended Daily Dose:	0.819	Skin Sensitization:	0.973
Carcinogencity:	0.783	Eye Corrosion:	0.001
Eye Irritation:	0.297	Respiratory Toxicity:	0.756
Drug-induced Neurotoxicity:	0.246	Ototoxicity:	0.618
Hematotoxicity:	0.246	Drug-induced Nephrotoxicity:	0.907
Genotoxicity:	0.831	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.199	Hek293 Cytotoxicity:	0.717
BCF:	1.546 ? 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:	4.827 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.368 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.867 ? 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
NPO41069	Sapium discolor	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30350995]

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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	14000.0	nM	PMID[30350995]

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 NPC485424 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	7621
0.1-0.2	38534
0.2-0.3	3454
0.3-0.4	177
0.4-0.5	56
0.5-0.6	8
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8488	Intermediate Similarity	NPC485425
0.7701	Intermediate Similarity	NPC485423
0.7051	Intermediate Similarity	NPC485429
0.6042	Remote Similarity	NPC485427
0.6042	Remote Similarity	NPC485426
0.6022	Remote Similarity	NPC325032
0.6022	Remote Similarity	NPC477483
0.5745	Remote Similarity	NPC327962
0.5435	Remote Similarity	NPC86257
0.5412	Remote Similarity	NPC30522
0.5412	Remote Similarity	NPC485428
0.5281	Remote Similarity	NPC485422
0.5196	Remote Similarity	NPC22676
0.51	Remote Similarity	NPC248287
0.51	Remote Similarity	NPC234548

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC485424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3375
0.1-0.2	5681
0.2-0.3	91
0.3-0.4	2
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