NPASS Compound

Natural Product: NPC509880

Natural Product ID	NPC509880
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	9,10,12,13,15,16-hexahydroxyheptacos-18-enoic acid
IUPAC Name	9,10,12,13,15,16-hexahydroxyheptacos-18-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 87 86 0 0 0 0 0 0 0 0999 V2000 -3.4419 -4.3930 -2.0300 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7836 -3.9519 -1.5311 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6481 -2.8240 -0.5391 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0056 -2.3916 -0.0290 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7733 -1.2556 0.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0442 -0.7623 1.5490 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9284 0.3183 2.5362 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4180 1.6403 2.1692 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0689 1.6470 1.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7841 2.1597 0.4068 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3857 2.1217 -0.0800 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9511 3.5401 -0.2852 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0240 4.1969 0.9239 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5033 3.5674 -0.8123 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6223 2.8951 -2.0485 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6163 2.8463 0.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8289 2.8922 -0.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2054 4.2638 -0.3115 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1464 2.3338 -1.6215 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8068 0.9895 -1.7689 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5861 2.5021 -1.9867 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5663 1.8347 -1.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5868 2.2051 0.2153 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4614 0.3631 -1.2544 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4282 -0.0056 -2.6058 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6006 -0.3776 -0.5591 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9309 0.0320 -1.0819 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0740 -0.7398 -0.5602 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3986 -0.7967 0.8636 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4877 -1.4588 1.8324 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3014 -2.9073 1.4206 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4273 -3.6952 2.3275 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0518 -3.2407 2.4830 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5323 -2.2557 1.9180 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2311 -3.9802 3.3525 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1126 -3.7389 -2.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6845 -4.2899 -1.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4901 -5.4492 -2.3783 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4203 -4.7559 -1.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3220 -3.5120 -2.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9933 -3.1306 0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1279 -1.9837 -1.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5744 -2.0002 -0.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5646 -3.2252 0.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1401 -1.7019 1.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1412 -0.5315 0.4661 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5257 -1.6433 2.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7874 -0.5017 0.7453 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9703 0.4756 2.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3219 -0.1091 3.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3690 2.2972 3.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1187 2.2088 1.4951 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2372 1.2252 2.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5573 2.5885 -0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7773 1.6209 0.6842 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3350 1.5154 -1.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5962 4.0733 -1.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2550 4.8306 1.0581 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2379 4.6094 -1.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3859 3.3093 -2.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8704 1.7653 0.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6602 3.2660 1.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4651 2.4677 0.5410 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9811 4.7044 0.5474 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5110 2.9321 -2.3626 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0688 0.6941 -1.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6757 2.0816 -3.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8230 3.5932 -2.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5932 2.1892 -1.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6047 1.5399 0.9074 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -0.0503 -0.7891 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1799 0.3718 -3.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3896 -1.4481 -0.7032 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4879 -0.1597 0.5241 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0862 1.1495 -0.8973 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9714 -0.0872 -2.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9878 -0.4152 -1.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9241 -1.8060 -0.9896 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3858 -1.3786 0.9409 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7173 0.2337 1.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0829 -1.5505 2.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5960 -0.9469 2.1432 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3234 -3.3898 1.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9200 -2.9175 0.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9132 -3.6538 3.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4640 -4.7594 1.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2325 -3.9197 3.3290 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 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 0 2 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 0 5 46 1 0 6 47 1 0 6 48 1 0 7 49 1 0 7 50 1 0 8 51 1 0 8 52 1 0 9 53 1 0 10 54 1 0 11 55 1 0 11 56 1 0 12 57 1 0 13 58 1 0 14 59 1 0 15 60 1 0 16 61 1 0 16 62 1 0 17 63 1 0 18 64 1 0 19 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 22 69 1 0 23 70 1 0 24 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 30 82 1 0 31 83 1 0 31 84 1 0 32 85 1 0 32 86 1 0 35 87 1 0 M END

Standard InCHIKey	ZHEGLTRCODOIQP-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C27H52O8/c1-2-3-4-5-6-7-8-10-13-16-21(28)23(30)19-25(32)26(33)20-24(31)22(29)17-14-11-9-12-15-18-27(34)35/h10,13,21-26,28-33H,2-9,11-12,14-20H2,1H3,(H,34,35)
SMILES	CCCCCCCCC=CCC(O)C(O)CC(O)C(O)CC(O)C(O)CCCCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.37	Volume:	540.597 ? Van der Waals volume.
Dense:	0.933	LogP:	3.823 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.729 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.834 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	2.0
TPSA:	158.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	7.0	Rings:	0.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.249	Fsp³:	0.889
MCE-18:	7.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.058	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.634	Promiscuous compounds:	0.227

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.275	MDCK Permeability:	-4.759
Pgp-inhibitor:	0.0	Pgp-substrate:	0.1
PAMPA:	0.996 ? 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):	0.939
20% Bioavailability (F20%):	0.937	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.932
Plasma Protein Binding (PPB):	91.333%	Volume Distribution (VD):	0.021
Fu:	6.47% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.291
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.037
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.775
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.971
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):

2.967

Half-life (T1/2):

1.302

ADMET: Toxicity

hERG Blockers:	0.095	hERG Blockers (10um):	0.411
Human Hepatotoxicity (H-HT):	0.24	Drug-induced Liver Injury (DILI):	0.002
AMES Toxicity:	0.006	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.848	Skin Sensitization:	0.025
Carcinogencity:	0.018	Eye Corrosion:	0.0
Eye Irritation:	0.019	Respiratory Toxicity:	0.105
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.999
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.688
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.008
A549 Cytotoxicity:	0.004	Hek293 Cytotoxicity:	0.057
BCF:	0.716 ? 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:	3.975 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.368 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.171 ? 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
NPO40501	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27186821]
NPO40501	Usnea longissima	Species	Parmeliaceae	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

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 NPC509880 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	29787
0.1-0.2	18149
0.2-0.3	1579
0.3-0.4	199
0.4-0.5	94
0.5-0.6	29
0.6-0.7	15
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
0.7333	Intermediate Similarity	NPC243532
0.7174	Intermediate Similarity	NPC321838
0.6444	Remote Similarity	NPC606120
0.6341	Remote Similarity	NPC424
0.6341	Remote Similarity	NPC36061
0.6341	Remote Similarity	NPC69510
0.6341	Remote Similarity	NPC77272
0.6341	Remote Similarity	NPC290563
0.6341	Remote Similarity	NPC139029
0.6341	Remote Similarity	NPC281972
0.6341	Remote Similarity	NPC261831
0.6341	Remote Similarity	NPC87564
0.625	Remote Similarity	NPC255863
0.625	Remote Similarity	NPC136164
0.625	Remote Similarity	NPC245947
0.62	Remote Similarity	NPC49863
0.6098	Remote Similarity	NPC281245
0.5952	Remote Similarity	NPC92114
0.5918	Remote Similarity	NPC99619
0.5909	Remote Similarity	NPC154245
0.5909	Remote Similarity	NPC85813
0.5909	Remote Similarity	NPC223697
0.5909	Remote Similarity	NPC6095
0.5882	Remote Similarity	NPC26500
0.5814	Remote Similarity	NPC95145
0.5814	Remote Similarity	NPC325642
0.5814	Remote Similarity	NPC65174
0.5682	Remote Similarity	NPC321062
0.5682	Remote Similarity	NPC324004
0.5682	Remote Similarity	NPC328497
0.5577	Remote Similarity	NPC323045
0.5577	Remote Similarity	NPC317881
0.549	Remote Similarity	NPC323477
0.5417	Remote Similarity	NPC323436
0.537	Remote Similarity	NPC605544
0.537	Remote Similarity	NPC607260
0.5333	Remote Similarity	NPC5413
0.5217	Remote Similarity	NPC52955
0.5217	Remote Similarity	NPC88966
0.5217	Remote Similarity	NPC25417
0.5217	Remote Similarity	NPC1813
0.5217	Remote Similarity	NPC59051
0.52	Remote Similarity	NPC477201
0.5094	Remote Similarity	NPC470320
0.5094	Remote Similarity	NPC327112
0.5091	Remote Similarity	NPC328653

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC509880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6404
0.1-0.2	2560
0.2-0.3	143
0.3-0.4	17
0.4-0.5	18
0.5-0.6	4
0.6-0.7	4
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
0.6341	Remote Similarity	NPD3195	Phase 2
0.6341	Remote Similarity	NPD3196	Approved
0.62	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3194	Phase 4
0.5909	Remote Similarity	NPD4266	Phase 2
0.5333	Remote Similarity	NPD3173	Phase 4
0.5217	Remote Similarity	NPD3172	Approved
0.5094	Remote Similarity	NPD4246	Phase 2

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