NPASS Compound

Natural Product: NPC310572

Natural Product ID	NPC310572
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Meliavolkinin
IUPAC Name	n.a.
Synonyms	Meliavolkinin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452721
PubChem CID	44566525
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 90 0 0 0 0 0 0 0 0999 V2000 -6.3145 1.4262 1.5154 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4086 2.0543 0.5200 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8458 3.0474 -0.1159 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1253 1.6053 0.2628 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2496 2.2029 -0.6912 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9253 1.2696 -1.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6060 0.5187 -1.7271 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8695 -0.5608 -0.8503 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8976 -1.8514 -1.2896 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6958 -2.1490 -2.5155 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1567 -2.9928 -0.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1876 -4.2973 -0.8433 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4400 -5.3446 0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6652 -5.0950 1.3708 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6375 -3.8006 1.8141 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 -2.7539 0.9226 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4902 1.3518 -1.1379 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0892 1.7788 0.1547 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1365 2.8249 0.0565 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8242 4.1852 -0.3897 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3287 2.9509 1.5790 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9531 3.1802 1.8870 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2520 2.1310 1.2976 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1456 2.4456 0.8909 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7218 1.4103 0.0087 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7440 0.5763 -0.7526 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3653 -0.1930 -1.8531 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6171 -0.9055 -1.4270 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8222 -0.9140 0.0522 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6507 0.4312 0.6780 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4012 0.4488 1.7616 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1387 -0.8819 1.9071 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2846 -1.1545 0.4244 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8575 -2.4045 0.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5801 -2.5405 -1.1760 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9950 -3.7732 -1.2652 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6111 -4.4646 -0.2285 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8942 -3.6380 0.6047 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9113 -1.8798 0.7320 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6759 2.1879 -0.9235 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8574 2.7308 2.0522 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2333 2.4335 -2.1379 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3497 1.4695 1.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2904 1.9439 2.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1023 0.3257 1.6324 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8597 3.0566 -1.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7675 0.5201 -1.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9379 1.7819 -2.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3562 0.1032 -2.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0167 -4.5183 -1.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4676 -6.3781 -0.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8663 -5.9090 2.0839 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8174 -3.6105 2.8725 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3815 -1.7631 1.3647 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6676 0.8744 0.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6257 4.8545 0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8953 4.6341 -0.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0081 4.3655 -1.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8737 3.8546 1.8491 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6815 2.0208 2.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1589 1.3586 2.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1501 3.4652 0.3823 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3376 -0.1668 -0.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6282 0.3670 -2.7729 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6874 -0.9867 -2.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6401 -1.9688 -1.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5482 -0.4626 -1.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4945 1.2706 2.4480 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0848 -0.7517 2.4270 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4218 -1.5659 2.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8278 -0.2681 -0.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7757 -1.7781 -1.9175 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8126 -5.5095 -0.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4359 -3.9056 1.5703 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3833 -1.4868 1.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4467 -2.7916 1.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1617 -2.3422 0.0188 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7470 1.7934 -1.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7148 2.2235 -0.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3945 3.2600 -0.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2708 2.9722 2.8116 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5605 2.0707 -2.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1449 3.3773 -1.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1026 2.6032 -2.8429 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 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 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 2 0 29 39 1 1 25 40 1 6 24 41 1 0 17 42 1 6 19 5 1 0 30 25 1 0 38 34 1 0 16 11 1 0 26 17 1 0 33 29 1 0 23 18 1 0 1 43 1 0 1 44 1 0 1 45 1 0 5 46 1 6 6 47 1 0 6 48 1 0 7 49 1 6 12 50 1 0 13 51 1 0 14 52 1 0 15 53 1 0 16 54 1 0 18 55 1 1 20 56 1 0 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 23 61 1 1 24 62 1 6 26 63 1 1 27 64 1 0 27 65 1 0 28 66 1 0 28 67 1 0 31 68 1 0 32 69 1 0 32 70 1 0 33 71 1 6 35 72 1 0 37 73 1 0 38 74 1 0 39 75 1 0 39 76 1 0 39 77 1 0 40 78 1 0 40 79 1 0 40 80 1 0 41 81 1 0 42 82 1 0 42 83 1 0 42 84 1 0 M END

Standard InCHIKey	OVRHPVPNJONXSX-YWQAOYTKSA-N
Standard InCHI	InChI=1S/C35H42O7/c1-20(36)41-26-17-27(42-31(38)21-9-7-6-8-10-21)35(5)25-13-15-32(2)23(22-14-16-39-18-22)11-12-24(32)34(25,4)30(37)28-29(35)33(26,3)19-40-28/h6-10,12,14,16,18,23,25-30,37H,11,13,15,17,19H2,1-5H3/t23-,25-,26+,27-,28-,29-,30+,32-,33+,34-,35-/m0/s1
SMILES	CC(=O)O[C@@H]1C[C@H](OC(=O)c2ccccc2)[C@]2([C@@H]3[C@]1(C)CO[C@@H]3[C@H]([C@@]1([C@@H]2CC[C@@]2(C1=CC[C@H]2c1cocc1)C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	574.29	Volume:	594.461 ? Van der Waals volume.
Dense:	0.966	LogP:	4.244 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.592 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.396 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	36.0
TPSA:	95.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	7.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.349	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.253	Fsp³:	0.6
MCE-18:	160.714 ? 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:	0.913	Fluc inhibitor:	0.176 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.022	Promiscuous compounds:	0.165

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.311	MDCK Permeability:	-4.788
Pgp-inhibitor:	0.983	Pgp-substrate:	0.029
PAMPA:	0.708 ? 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%):	0.618	30% Bioavailability (F30%):	0.4
50% Bioavailability (F50%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095	MRP1:	0.994
Plasma Protein Binding (PPB):	95.562%	Volume Distribution (VD):	-0.165
Fu:	4.089% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.9	BCRP inhibitor:	0.272
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.025	CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.976	CYP3A4-substrate:	0.069
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.649 ? 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):

9.396

Half-life (T1/2):

0.656

ADMET: Toxicity

hERG Blockers:	0.162	hERG Blockers (10um):	0.464
Human Hepatotoxicity (H-HT):	0.252	Drug-induced Liver Injury (DILI):	0.932
AMES Toxicity:	0.498	Rat Oral Acute Toxicity:	0.752
Maximum Recommended Daily Dose:	0.98	Skin Sensitization:	0.955
Carcinogencity:	0.877	Eye Corrosion:	0.0
Eye Irritation:	0.073	Respiratory Toxicity:	0.71
Drug-induced Neurotoxicity:	0.283	Ototoxicity:	0.437
Hematotoxicity:	0.067	Drug-induced Nephrotoxicity:	0.797
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.107
A549 Cytotoxicity:	0.613	Hek293 Cytotoxicity:	0.588
BCF:	1.006 ? 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:	4.172 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.784 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.271 ? 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
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217705]
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461654]
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4571	Melia volkensii	Species	Meliaceae	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	6

Activity Type	# Activity
Cell line	6

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	=	25.36	ug ml-1	PMID[25798528]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	27.84	ug ml-1	PMID[25906087]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	28.07	ug ml-1	PMID[25420236]
NPT376	Cell line	A498	Homo sapiens	ED50	=	26.88	ug ml-1	PMID[25420236]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	1.02	ug ml-1	PMID[25420236]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	16.73	ug ml-1	PMID[25420236]

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
-	Aedes aegypti	LC50	=	59.7	ug.mL-1	PMID[22194678]
-	Artemia	LC50	=	5.37	ug.mL-1	PMID[22194678]

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 NPC310572 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	10195
0.1-0.2	36068
0.2-0.3	3252
0.3-0.4	285
0.4-0.5	37
0.5-0.6	14
0.6-0.7	3
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8395	Intermediate Similarity	NPC34421
0.8395	Intermediate Similarity	NPC237259
0.8193	Intermediate Similarity	NPC98206
0.6562	Remote Similarity	NPC608643
0.6238	Remote Similarity	NPC11062
0.6154	Remote Similarity	NPC196846
0.5824	Remote Similarity	NPC471007
0.5699	Remote Similarity	NPC33938
0.551	Remote Similarity	NPC609027
0.5455	Remote Similarity	NPC471003
0.5354	Remote Similarity	NPC155939
0.5354	Remote Similarity	NPC470995
0.5319	Remote Similarity	NPC253201
0.5294	Remote Similarity	NPC470792
0.5258	Remote Similarity	NPC601664
0.5208	Remote Similarity	NPC302054
0.5192	Remote Similarity	NPC610301
0.5189	Remote Similarity	NPC126984
0.5104	Remote Similarity	NPC470997
0.5049	Remote Similarity	NPC610307

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC310572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3028
0.1-0.2	6006
0.2-0.3	115
0.3-0.4	1
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