NPASS Compound

Natural Product: NPC6255

Natural Product ID	NPC6255
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2R,4Ar,5R,6Ar,6As,6Br,8Ar,9R,12Ar,14Bs)-5-Hydroxy-2,9-Bis(Hydroxymethyl)-2,6A,6B,9,12A-Pentamethyl-10-Oxo-3,4,5,6,6A,7,8,8A,11,12,13,14B-Dodecahydro-1H-Picene-4A-Carboxylic Acid
IUPAC Name	(2R,4aR,5R,6aR,6aS,6bR,8aR,9R,12aR,14bS)-5-hydroxy-2,9-bis(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1910833
PubChem CID	54671898
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 86 0 0 0 0 0 0 0 0999 V2000 -6.6402 -1.0959 -2.3616 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3944 -1.5178 -1.9150 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9589 -0.6402 -0.7335 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9882 -0.8080 0.3277 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7670 0.7353 -1.2552 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2828 1.6301 -0.1763 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3621 1.0675 0.8310 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8685 -0.3034 0.6566 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6081 -1.1729 -0.3157 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4123 -0.4580 0.3817 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8202 -1.5715 0.8149 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5944 -1.9225 0.6521 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4284 -0.8626 0.0387 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8762 0.5283 0.1396 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5576 0.5143 -0.3358 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2237 1.8676 -0.2069 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1377 1.9886 0.9672 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5643 3.3212 1.0188 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6098 0.1946 -1.8391 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9237 1.1195 1.5191 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7097 1.3443 -0.8444 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1522 1.3915 -0.3170 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6825 -0.0091 -0.4235 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8827 -0.9983 0.4012 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2184 -1.0393 1.8329 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2718 -2.3790 -0.1766 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7148 -2.6871 0.0904 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5473 -1.4719 0.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6194 -1.5769 0.7760 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1488 -0.1377 -0.2946 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8201 0.8973 0.5599 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7819 -0.0284 -1.6738 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5050 1.1832 -2.2817 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0377 1.2617 2.1744 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2851 0.2545 2.8758 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3919 2.5036 2.6576 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0560 -0.4527 -1.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6603 -1.4236 -2.7410 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5013 -2.5736 -1.5877 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4022 0.1124 0.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8708 -1.4344 0.0004 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5236 -1.4558 1.1304 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7632 1.1021 -1.6319 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0524 0.6785 -2.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8131 2.5207 -0.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2027 2.1133 0.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0215 -0.8177 1.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8207 -2.2080 0.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0479 -1.3800 -1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4344 -2.3187 1.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6177 -2.8502 0.0056 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9573 -2.2834 1.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4234 -1.0738 -1.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4835 2.6982 -0.2034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8645 2.1079 -1.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7127 1.7560 1.9401 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8763 3.8151 1.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0816 0.9972 -2.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3232 -0.8193 -2.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 0.3878 -2.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2960 0.4812 2.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9070 1.1684 1.9814 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5832 2.1758 1.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8076 0.6975 -1.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3205 2.3351 -1.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2468 1.8752 0.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7038 2.0117 -1.0619 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4269 -0.3201 -1.4852 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8648 -0.1830 2.1885 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3509 -1.1101 2.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8452 -1.9390 2.1233 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9614 -2.4819 -1.2143 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6808 -3.1121 0.4295 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8668 -3.3006 1.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0601 -3.3482 -0.7585 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2775 1.8223 0.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8268 1.1899 0.1332 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0841 0.4724 1.5673 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9037 -0.0929 -1.5741 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5059 -0.8941 -2.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2454 1.5841 -2.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5293 2.6479 3.6672 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 15 19 1 6 14 20 1 1 14 21 1 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 1 30 32 1 0 32 33 1 0 7 34 1 1 34 35 2 0 34 36 1 0 9 3 1 0 15 10 1 0 30 23 1 0 17 7 1 0 24 13 1 0 1 37 1 0 2 38 1 0 2 39 1 0 4 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 8 47 1 1 9 48 1 0 9 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 6 16 54 1 0 16 55 1 0 17 56 1 1 18 57 1 0 19 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 6 25 69 1 0 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 31 76 1 0 31 77 1 0 31 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 36 82 1 0 M END

Standard InCHIKey	XRUBFYYNZLBFBN-JYGFFPNFSA-N
Standard InCHI	InChI=1S/C30H46O6/c1-25(16-31)12-13-30(24(35)36)19(14-25)18-6-7-21-26(2)10-9-22(33)27(3,17-32)20(26)8-11-28(21,4)29(18,5)15-23(30)34/h6,19-21,23,31-32,34H,7-17H2,1-5H3,(H,35,36)/t19-,20+,21+,23+,25+,26-,27-,28+,29+,30+/m0/s1
SMILES	OC[C@]1(C)CC[C@]2([C@@H](C1)C1=CC[C@H]3[C@@]([C@@]1(C[C@H]2O)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)[C@@]1(C)CO)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.33	Volume:	529.486 ? Van der Waals volume.
Dense:	0.949	LogP:	2.52 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.609 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.009 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	115.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.426	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.163	Fsp³:	0.867
MCE-18:	107.143 ? 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:	0.646	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.319	Promiscuous compounds:	0.274

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.601	MDCK Permeability:	-5.044
Pgp-inhibitor:	0.001	Pgp-substrate:	0.017
PAMPA:	1.0 ? 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%):	0.437	30% Bioavailability (F30%):	0.008
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797	MRP1:	0.7
Plasma Protein Binding (PPB):	81.892%	Volume Distribution (VD):	-0.259
Fu:	15.955% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.074	BCRP inhibitor:	0.918
BSEP inhibitor:	0.981

ADMET: Metabolism

CYP1A2-inhibitor:	0.016	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.082	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.36	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.024
HLM stability:	0.0 ? 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):

2.155

Half-life (T1/2):

1.415

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.848	Drug-induced Liver Injury (DILI):	0.109
AMES Toxicity:	0.212	Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.181	Skin Sensitization:	0.989
Carcinogencity:	0.968	Eye Corrosion:	0.0
Eye Irritation:	0.229	Respiratory Toxicity:	0.456
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.847
Hematotoxicity:	0.757	Drug-induced Nephrotoxicity:	0.98
Genotoxicity:	0.369	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.191	Hek293 Cytotoxicity:	0.128
BCF:	0.483 ? 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:	3.277 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.916 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.978 ? 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
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21870831]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	stem bark	Purchased from an herbal market at Kumsan, Chungnam, Korea	2009-AUG	PMID[21870831]
NPO30412	Kalopanax pictus	Species	Araliaceae	Eukaryota	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	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	6500.0	nM	PMID[21870831]

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 NPC6255 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	18827
0.1-0.2	26025
0.2-0.3	4097
0.3-0.4	690
0.4-0.5	183
0.5-0.6	21
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
0.6761	Remote Similarity	NPC158141
0.6486	Remote Similarity	NPC471588
0.6438	Remote Similarity	NPC228784
0.6438	Remote Similarity	NPC324341
0.6438	Remote Similarity	NPC601810
0.64	Remote Similarity	NPC222047
0.6351	Remote Similarity	NPC201657
0.6267	Remote Similarity	NPC148964
0.6216	Remote Similarity	NPC173089
0.5946	Remote Similarity	NPC182797
0.5946	Remote Similarity	NPC52169
0.5946	Remote Similarity	NPC488562
0.5867	Remote Similarity	NPC472149
0.5867	Remote Similarity	NPC609452
0.5783	Remote Similarity	NPC476890
0.5783	Remote Similarity	NPC476889
0.575	Remote Similarity	NPC601365
0.5733	Remote Similarity	NPC121798
0.5733	Remote Similarity	NPC234346
0.5517	Remote Similarity	NPC31839
0.5455	Remote Similarity	NPC38754
0.5375	Remote Similarity	NPC324063
0.5281	Remote Similarity	NPC242611
0.5161	Remote Similarity	NPC76999
0.5065	Remote Similarity	NPC274050
0.5065	Remote Similarity	NPC162632
0.5063	Remote Similarity	NPC231063
0.5063	Remote Similarity	NPC282395
0.5063	Remote Similarity	NPC88116
0.5063	Remote Similarity	NPC110308

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC6255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5372
0.1-0.2	3684
0.2-0.3	90
0.3-0.4	4
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