NPASS Compound

Natural Product: NPC134451

Natural Product ID	NPC134451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PHKSUFCCGLWIMC-SIKIZQCASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	12310372
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

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 51 53 0 0 0 0 0 0 0 0999 V2000 0.0753 2.8482 -0.8695 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0975 1.3609 -1.0648 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1494 0.9497 -1.8473 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3014 1.0483 -0.8703 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1919 -0.0181 0.1446 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0161 0.4012 1.3439 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5888 1.5967 1.8904 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8093 -1.2901 -0.3044 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5289 -2.3367 0.4963 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6979 -2.2839 1.7084 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7865 -1.0729 1.7925 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7667 -0.3903 0.4611 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3043 0.5677 0.1901 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7085 1.5128 1.2735 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5774 -0.2826 -0.0486 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7972 0.5152 -0.3095 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9066 -0.4874 -0.5232 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7515 -1.0412 0.4105 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6066 -1.9117 -0.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2632 -1.8528 -1.5124 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2676 -1.0316 -1.7317 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6250 -1.5410 -1.4375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0707 -2.7223 -1.6679 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9916 -0.5823 -2.3468 O 0 0 0 0 0 1 0 0 0 0 0 0 -0.5100 3.2128 -0.0275 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1201 3.2685 -0.8817 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4021 3.2930 -1.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9266 1.1793 -1.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0503 -0.0308 -2.3169 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3028 1.7189 -2.6233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1600 2.0836 -0.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2281 1.1643 -1.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0821 0.6033 1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1105 -0.3335 2.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0515 2.3699 1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9575 -3.2887 0.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0535 -3.2247 1.6456 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2809 -2.4652 2.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0631 -0.3970 2.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2298 -1.4479 2.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5537 -1.2635 -0.2688 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1878 0.9365 2.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0303 2.1929 1.6617 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4950 2.1869 0.8062 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7793 -0.9269 0.8267 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4144 -0.9641 -0.9060 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8154 1.1480 -1.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1590 1.1119 0.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7273 -0.8197 1.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3733 -2.4793 0.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7767 -0.7841 -2.6619 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 1 0 5 6 1 1 6 7 1 0 5 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 8 22 1 0 22 23 2 0 22 24 1 0 13 2 1 0 21 17 2 0 12 5 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 6 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 6 33 1 0 6 34 1 0 7 35 1 0 9 36 1 0 10 37 1 0 10 38 1 0 11 39 1 0 11 40 1 0 12 41 1 6 14 42 1 0 14 43 1 0 14 44 1 0 15 45 1 0 15 46 1 0 16 47 1 0 16 48 1 0 18 49 1 0 19 50 1 0 21 51 1 0 M CHG 1 24 -1 M END

Standard InCHIKey	PHKSUFCCGLWIMC-SIKIZQCASA-N
Standard InCHI	InChI=1S/C20H28O4/c1-14-6-10-20(13-21)16(18(22)23)4-3-5-17(20)19(14,2)9-7-15-8-11-24-12-15/h4,8,11-12,14,17,21H,3,5-7,9-10,13H2,1-2H3,(H,22,23)/p-1/t14-,17-,19+,20-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CO)C(=CCC[C@@H]2[C@@]1(C)CCc1ccoc1)C(=O)[O-]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	332.2	Volume:	353.422 ? Van der Waals volume.
Dense:	0.94	LogP:	2.615 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.255 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.363 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	17.0
TPSA:	70.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.853	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.355	Fsp³:	0.65
MCE-18:	69.697 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.044	Fluc inhibitor:	0.03 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.171	Promiscuous compounds:	0.061

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.339	MDCK Permeability:	-4.923
Pgp-inhibitor:	0.002	Pgp-substrate:	0.114
PAMPA:	0.987 ? 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):	0.236
20% Bioavailability (F20%):	0.813	30% Bioavailability (F30%):	0.667
50% Bioavailability (F50%):	0.872

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085	MRP1:	0.886
Plasma Protein Binding (PPB):	86.715%	Volume Distribution (VD):	-0.711
Fu:	10.946% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.771
OATP1B3 inhibitor:	0.332	BCRP inhibitor:	0.248
BSEP inhibitor:	0.344

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.007 ? 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):

3.226

Half-life (T1/2):

1.182

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.159
Human Hepatotoxicity (H-HT):	0.476	Drug-induced Liver Injury (DILI):	0.642
AMES Toxicity:	0.286	Rat Oral Acute Toxicity:	0.571
Maximum Recommended Daily Dose:	0.64	Skin Sensitization:	0.452
Carcinogencity:	0.517	Eye Corrosion:	0.004
Eye Irritation:	0.829	Respiratory Toxicity:	0.714
Drug-induced Neurotoxicity:	0.061	Ototoxicity:	0.621
Hematotoxicity:	0.288	Drug-induced Nephrotoxicity:	0.518
Genotoxicity:	0.778	RPMI-8226 Immunitoxicity:	0.029
A549 Cytotoxicity:	0.052	Hek293 Cytotoxicity:	0.115
BCF:	0.566 ? 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:	3.462 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.977 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.077 ? 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
NPO19190	Garcinia vieillardii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104511]
NPO19190	Garcinia vieillardii	Species	Clusiaceae	Eukaryota	n.a.	stem	n.a.	PMID[15104511]
NPO19190	Garcinia vieillardii	Species	Clusiaceae	Eukaryota	n.a.	stem	n.a.	PMID[17826924]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19435339]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO19058	Loranthus europaeus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14841	Streptomyces variabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19190	Garcinia vieillardii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14174	Frankenia pulverulenta	Species	Frankeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13525	Erythraea centaurium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15950	Acacia baileyana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27734	Verbesina coahuilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17832	Ocotea bullata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17832	Ocotea bullata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14356	Acronychia vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14356	Acronychia vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15950	Acacia baileyana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23335	Caroxylon imbricatum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14356	Acronychia vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13133	Brickellia brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18633	Berberis guimpelii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14174	Frankenia pulverulenta	Species	Frankeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19190	Garcinia vieillardii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6967	Bersama engleriana	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1316	Vernonia monocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18794	Diplostephium floribundum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13525	Erythraea centaurium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14841	Streptomyces variabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27734	Verbesina coahuilensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO680	Citrus lumia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16577	Padina vickersiae	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19058	Loranthus europaeus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17832	Ocotea bullata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13964	Tetradenia barberae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9093	Selenastrum capricornutum	Species	Selenastraceae	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

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

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 NPC134451 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	13007
0.1-0.2	35371
0.2-0.3	1348
0.3-0.4	110
0.4-0.5	18
0.5-0.6	2
0.6-0.7	2
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
0.7759	Intermediate Similarity	NPC112706
0.625	Remote Similarity	NPC207294
0.6032	Remote Similarity	NPC23086
0.5312	Remote Similarity	NPC476947
0.5217	Remote Similarity	NPC289537

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3216
0.1-0.2	5890
0.2-0.3	42
0.3-0.4	2
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