NPASS Compound

Natural Product: NPC253738

Natural Product ID	NPC253738
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Reissantin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507618
PubChem CID	11763527
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 84 88 0 0 0 0 0 0 0 0999 V2000 -1.8426 -4.9645 2.6242 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2216 -3.6216 2.4881 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6784 -3.1180 3.4943 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1627 -2.8521 1.3986 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6399 -1.6265 1.1243 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6480 -1.6230 0.3246 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3075 -0.2934 0.6758 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6498 -0.1976 0.4174 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6483 -0.0217 1.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2650 0.0538 2.5660 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0560 0.0702 1.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9850 0.2452 2.0181 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3390 0.3387 1.7392 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7392 0.2529 0.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9538 0.3335 0.1471 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8436 0.0815 -0.5656 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5296 -0.0074 -0.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3351 -0.0011 -1.9227 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4017 0.5832 -0.1282 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8759 0.8281 0.6145 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5712 -0.5039 0.8677 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5846 -0.7530 -0.0784 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9503 -0.7785 0.1856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2906 -0.5601 1.3707 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9670 -1.0387 -0.8209 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6892 -1.2854 -2.1473 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7288 -1.5243 -3.0400 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0366 -1.5235 -2.6442 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3276 -1.2768 -1.3136 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2908 -1.0413 -0.4372 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7104 1.5570 1.9183 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7690 1.7545 -0.2165 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2583 1.9809 -1.6125 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1585 2.4491 -1.6771 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0681 1.8017 -0.6738 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6199 2.7384 0.3423 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1763 1.3187 -1.4209 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8992 3.0407 0.3598 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1023 3.5776 0.6937 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1400 2.8978 0.4787 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1510 4.9378 1.2962 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0783 -0.1609 -1.2662 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4952 -1.4511 -1.1361 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7355 -1.7996 -1.8699 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5541 -2.3355 -1.7783 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9623 -5.4929 1.6720 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8419 -4.8106 3.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2727 -5.6042 3.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2251 -1.3932 2.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2438 -2.4717 0.6598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1993 -0.2028 1.7760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6393 0.3109 3.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0689 0.4747 2.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8087 -0.1443 -1.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3934 -0.3316 -1.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2368 0.9688 -2.4426 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7126 -0.7663 -2.4358 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1709 -0.3449 1.8159 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6566 -1.2837 -2.4525 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4867 -1.7167 -4.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8711 -1.7076 -3.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3705 -1.2781 -1.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5578 -0.8496 0.6075 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5853 2.6508 1.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0188 1.2043 2.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7145 1.4620 2.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7897 1.3545 -0.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8731 2.8533 -2.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5121 1.1662 -2.3220 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2245 3.5606 -1.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4990 2.3388 -2.7309 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7441 2.2895 1.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6620 3.0819 0.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0469 3.7117 0.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6138 2.1399 -1.7836 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8130 5.6806 0.5444 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4565 5.0344 2.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1665 5.1936 1.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7619 -2.8953 -2.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6834 -1.5692 -1.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6775 -1.2886 -2.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0275 -2.9886 -0.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1539 -3.0574 -2.5164 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3184 -1.7605 -2.3275 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 2 0 9 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 16 18 1 0 7 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 20 31 1 1 20 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 6 32 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 19 42 1 6 42 43 1 0 43 44 1 0 43 45 1 0 21 5 1 0 30 25 1 0 43 6 1 0 17 11 2 0 35 19 1 0 1 46 1 0 1 47 1 0 1 48 1 0 5 49 1 1 6 50 1 6 7 51 1 1 12 52 1 0 13 53 1 0 17 54 1 0 18 55 1 0 18 56 1 0 18 57 1 0 21 58 1 1 26 59 1 0 27 60 1 0 28 61 1 0 29 62 1 0 30 63 1 0 31 64 1 0 31 65 1 0 31 66 1 0 32 67 1 6 33 68 1 0 33 69 1 0 34 70 1 0 34 71 1 0 36 72 1 0 36 73 1 0 36 74 1 0 37 75 1 0 41 76 1 0 41 77 1 0 41 78 1 0 44 79 1 0 44 80 1 0 44 81 1 0 45 82 1 0 45 83 1 0 45 84 1 0 M END

Standard InCHIKey	PEFXNCJFEYSZKT-GXNYSBAXSA-N
Standard InCHI	InChI=1S/C33H39NO11/c1-18(35)41-22-15-16-31(5,40)33-26(43-29(39)21-13-14-23(37)34(7)17-21)24(30(3,4)45-33)25(42-19(2)36)27(32(22,33)6)44-28(38)20-11-9-8-10-12-20/h8-14,17,22,24-27,40H,15-16H2,1-7H3/t22-,24+,25-,26+,27-,31-,32-,33-/m0/s1
SMILES	CC(=O)O[C@H]1[C@@H]2[C@@H](OC(=O)c3ccc(=O)n(c3)C)[C@]3([C@@]([C@H]1OC(=O)c1ccccc1)(C)[C@H](CC[C@]3(C)O)OC(=O)C)OC2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	625.25	Volume:	617.866 ? Van der Waals volume.
Dense:	1.012	LogP:	1.302 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.736 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.323 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	31.0
TPSA:	156.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.372	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.849	Fsp³:	0.545
MCE-18:	177.255 ? 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:	0.165	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.139 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.044

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.425	MDCK Permeability:	-4.844
Pgp-inhibitor:	1.0	Pgp-substrate:	0.291
PAMPA:	0.712 ? 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%):	0.934	30% Bioavailability (F30%):	0.957
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	59.657%	Volume Distribution (VD):	-0.172
Fu:	36.772% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.003
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.295	CYP3A4-substrate:	0.37
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.993 ? 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):

4.164

Half-life (T1/2):

0.686

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.321
Human Hepatotoxicity (H-HT):	0.186	Drug-induced Liver Injury (DILI):	0.467
AMES Toxicity:	0.237	Rat Oral Acute Toxicity:	0.494
Maximum Recommended Daily Dose:	0.588	Skin Sensitization:	0.592
Carcinogencity:	0.386	Eye Corrosion:	0.002
Eye Irritation:	0.221	Respiratory Toxicity:	0.241
Drug-induced Neurotoxicity:	0.129	Ototoxicity:	0.399
Hematotoxicity:	0.117	Drug-induced Nephrotoxicity:	0.435
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.045
A549 Cytotoxicity:	0.01	Hek293 Cytotoxicity:	0.104
BCF:	0.53 ? 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:	3.523 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.567 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.839 ? 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
NPO28607	Reissantia buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640511]
NPO28607	Reissantia buchananii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28607	Reissantia buchananii	Species	Celastraceae	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	9

Activity Type	# Activity
Cell line	9

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
NPT81	Cell line	A549	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[20503985]
NPT83	Cell line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[19173621]
NPT180	Cell line	HCT-8	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[19173621]
NPT91	Cell line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[19216517]
NPT306	Cell line	PC-3	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[20503985]
NPT309	Cell line	1A9	Homo sapiens	ED50	>	20.0	ug ml-1	PubChem BioAssay data set
NPT310	Cell line	1A9/ptx-10	Homo sapiens	ED50	>	20.0	ug ml-1	PubChem BioAssay data set

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 NPC253738 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	12517
0.1-0.2	35551
0.2-0.3	1409
0.3-0.4	258
0.4-0.5	94
0.5-0.6	14
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
0.7945	Intermediate Similarity	NPC163719
0.7945	Intermediate Similarity	NPC95810
0.7927	Intermediate Similarity	NPC30171
0.7439	Intermediate Similarity	NPC301368
0.7439	Intermediate Similarity	NPC84815
0.6706	Remote Similarity	NPC610927
0.6322	Remote Similarity	NPC125106
0.6322	Remote Similarity	NPC472573
0.6173	Remote Similarity	NPC200471
0.6173	Remote Similarity	NPC472575
0.5882	Remote Similarity	NPC57628
0.5663	Remote Similarity	NPC483886
0.5476	Remote Similarity	NPC87448
0.5412	Remote Similarity	NPC291599
0.5385	Remote Similarity	NPC4421
0.5349	Remote Similarity	NPC472572
0.5341	Remote Similarity	NPC472570
0.5301	Remote Similarity	NPC66761
0.5301	Remote Similarity	NPC483843
0.5294	Remote Similarity	NPC281717
0.5263	Remote Similarity	NPC470154
0.5158	Remote Similarity	NPC148896
0.5106	Remote Similarity	NPC611111
0.5054	Remote Similarity	NPC212768

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC253738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3470
0.1-0.2	5594
0.2-0.3	86
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