NPASS Compound

Natural Product: NPC317590

Natural Product ID	NPC317590
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Meliasenin L
IUPAC Name	(5R,9R,10R,13S,14S,16S,17S)-17-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-16-hydroxy-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms	Meliasenin L
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1641920
PubChem CID	50900150
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 82 85 0 0 0 0 0 0 0 0999 V2000 5.0070 3.0926 -1.2311 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7216 2.1486 -0.7105 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5393 0.9591 -1.3988 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7988 0.4836 -2.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9288 0.3917 -3.3517 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9789 0.0868 -1.2077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9631 -0.1225 -0.4841 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6242 0.3044 0.0729 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0958 -0.7893 0.9662 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7670 -0.4800 1.5730 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3867 -1.6909 2.4128 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4283 -1.4666 3.7663 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0567 -2.0046 2.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5403 -0.6461 1.6753 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6095 -0.2443 0.7287 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5700 -1.0858 -0.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2954 1.1732 0.3561 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9573 1.2673 -0.4702 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9512 0.2098 -0.2802 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8235 -0.5561 0.9905 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8762 -1.1581 1.5303 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2317 -1.1544 0.9592 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2603 -0.4447 -0.3379 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3884 0.7739 -0.2893 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5869 1.6362 0.9021 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 1.6003 -1.5577 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1682 0.8035 -2.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5133 0.4021 -2.2247 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5162 0.5278 -2.9002 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6417 -0.1850 -0.8702 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5104 0.6589 -0.0079 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3171 -1.5453 -1.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5698 0.1690 2.9375 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0597 -0.9826 2.1302 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4827 3.9453 -1.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8186 1.1567 -2.2187 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8160 0.0556 -3.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0776 0.6778 -3.9581 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9144 0.5311 -1.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0376 -1.0359 -1.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7579 0.3273 -0.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6975 -0.4297 0.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8508 -1.0240 -1.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7331 1.2583 0.5838 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9462 0.3379 -0.8219 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1557 -1.7412 0.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9672 0.4010 2.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9728 -2.5959 2.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8621 -2.2590 4.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6312 -2.3128 2.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1784 -2.7991 1.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1804 -1.9019 -0.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3467 -0.4671 -1.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5323 -1.6389 -0.7133 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0977 1.6980 -0.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1244 1.8111 1.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6584 1.2988 -1.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4202 2.2730 -0.2959 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9945 -0.5267 -1.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7641 -1.7142 2.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5083 -2.2403 0.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9567 -0.7725 1.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7824 -1.1355 -1.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6710 2.0739 1.2970 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1054 1.1386 1.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2503 2.5111 0.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5733 1.9742 -1.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1832 2.4850 -1.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5277 -0.0568 -2.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2645 1.5016 -3.5343 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4827 0.4029 1.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3575 1.7468 -0.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5754 0.4718 -0.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8675 -1.8297 -0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5276 -2.3401 -1.1532 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9396 -1.5933 -1.9308 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5341 0.7617 2.9477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2147 0.8906 3.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6523 -0.4497 3.8670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5102 -0.7955 3.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4788 -2.0023 2.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8480 -0.2005 2.0884 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 2 0 4 6 1 0 3 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 30 32 1 0 14 33 1 1 9 34 1 0 15 10 1 0 24 19 1 0 20 14 1 0 30 23 1 0 1 35 1 0 3 36 1 0 5 37 1 0 5 38 1 0 6 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 9 46 1 6 10 47 1 1 11 48 1 1 12 49 1 0 13 50 1 0 13 51 1 0 16 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 6 21 60 1 0 22 61 1 0 22 62 1 0 23 63 1 6 25 64 1 0 25 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 27 69 1 0 27 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	GMYOLHJETWNFPY-UUKLBSCWSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(2)23(34-33)11-9-19(3)26-22(31)17-30(8)21-10-12-24-27(4,5)25(32)14-15-28(24,6)20(21)13-16-29(26,30)7/h10,19-20,22-24,26,31,33H,1,9,11-17H2,2-8H3/t19-,20+,22+,23?,24+,26-,28-,29+,30-/m1/s1
SMILES	OOC(C(=C)C)CC[C@H]([C@@H]1[C@@H](O)C[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	4.859 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.14 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.712 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	22.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.248	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.13	Fsp³:	0.833
MCE-18:	82.8 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.934	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.303	Promiscuous compounds:	0.127

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.957	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.335	Pgp-substrate:	0.0
PAMPA:	0.095 ? 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%):	0.003	30% Bioavailability (F30%):	0.012
50% Bioavailability (F50%):	0.784

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.502	MRP1:	0.588
Plasma Protein Binding (PPB):	93.116%	Volume Distribution (VD):	0.123
Fu:	7.837% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.695
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.998	CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.56 ? 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):

10.577

Half-life (T1/2):

0.574

ADMET: Toxicity

hERG Blockers:	0.097	hERG Blockers (10um):	0.124
Human Hepatotoxicity (H-HT):	0.757	Drug-induced Liver Injury (DILI):	0.777
AMES Toxicity:	0.86	Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.634	Skin Sensitization:	0.994
Carcinogencity:	0.93	Eye Corrosion:	0.002
Eye Irritation:	0.084	Respiratory Toxicity:	0.306
Drug-induced Neurotoxicity:	0.238	Ototoxicity:	0.692
Hematotoxicity:	0.747	Drug-induced Nephrotoxicity:	0.767
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.102
A549 Cytotoxicity:	0.027	Hek293 Cytotoxicity:	0.752
BCF:	1.801 ? 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:	4.116 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.659 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.995 ? 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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

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	2

Activity Type	# Activity
Cell line	2

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
NPT1045	Cell line	U2OS	Homo sapiens	IC50	=	9.5	ug.mL-1	PMID[20961091]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	9.8	ug.mL-1	PMID[20961091]

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 NPC317590 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	21858
0.1-0.2	23740
0.2-0.3	3855
0.3-0.4	335
0.4-0.5	34
0.5-0.6	18
0.6-0.7	9
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
0.7619	Intermediate Similarity	NPC469994
0.7581	Intermediate Similarity	NPC82902
0.7273	Intermediate Similarity	NPC320026
0.7077	Intermediate Similarity	NPC2983
0.6957	Remote Similarity	NPC474327
0.6769	Remote Similarity	NPC474218
0.6567	Remote Similarity	NPC171441
0.6301	Remote Similarity	NPC57416
0.625	Remote Similarity	NPC218383
0.6197	Remote Similarity	NPC154101
0.6164	Remote Similarity	NPC271387
0.6164	Remote Similarity	NPC153792
0.6111	Remote Similarity	NPC107243
0.5714	Remote Similarity	NPC90652
0.5714	Remote Similarity	NPC155255
0.5714	Remote Similarity	NPC260992
0.5694	Remote Similarity	NPC486521
0.5694	Remote Similarity	NPC262870
0.5405	Remote Similarity	NPC67831
0.5405	Remote Similarity	NPC174051
0.5395	Remote Similarity	NPC273669
0.5395	Remote Similarity	NPC484802
0.5395	Remote Similarity	NPC118647
0.5362	Remote Similarity	NPC470078
0.5278	Remote Similarity	NPC470417
0.527	Remote Similarity	NPC471224
0.5143	Remote Similarity	NPC1319
0.5135	Remote Similarity	NPC318390
0.5068	Remote Similarity	NPC470052
0.5063	Remote Similarity	NPC322063
0.5062	Remote Similarity	NPC484792

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC317590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7320
0.1-0.2	1758
0.2-0.3	71
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