NPASS Compound

Natural Product: NPC150168

Natural Product ID	NPC150168
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UFSZVMQWXGMGET-HOFJZWJUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	49798966
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

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 84 0 0 0 0 0 0 0 0999 V2000 5.5608 -0.0611 5.5532 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4753 0.8492 5.0947 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0730 0.7327 3.8143 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7196 -0.2770 2.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4279 0.2490 1.7373 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6095 0.9555 0.7468 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5494 0.4496 -0.5010 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7274 1.1221 -1.5323 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7909 0.0990 -2.1474 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2739 -0.6928 -3.1731 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4461 -1.6668 -3.6872 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1705 -1.8858 -3.2254 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6839 -1.0794 -2.1839 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5139 -0.1073 -1.6768 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0299 0.6901 -0.6496 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5937 -1.3506 -1.7495 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0328 -0.6433 -0.8225 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3919 -2.3366 -2.2691 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6578 -2.5576 -1.7732 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2480 -1.7974 -0.6936 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8615 -0.4899 -1.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1427 -0.2252 -0.6831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9182 -1.2884 0.0328 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7227 1.0934 -1.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1872 1.8138 0.2571 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9925 2.0172 1.1544 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6239 3.2155 1.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4457 3.4068 2.4228 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4046 4.4048 1.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3312 -3.6101 -2.4134 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7970 -4.3516 -3.4319 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5390 -4.0897 -3.8813 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8176 -3.0733 -3.2980 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4041 -2.8188 -3.7167 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5649 -5.3718 -3.9936 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6287 -3.8666 -1.9298 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5411 -0.5351 -3.6833 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1601 -1.2409 -4.6985 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9191 2.2137 1.0918 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8735 1.8441 5.9956 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2138 -1.1334 5.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5134 0.0690 5.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7751 0.1624 6.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2658 1.3901 3.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4845 -0.8190 3.5455 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9318 -1.0273 2.6577 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2286 0.9535 2.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9897 -0.6004 1.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1137 -0.4451 -0.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1051 1.8916 -1.0379 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3665 1.5793 -2.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8070 -2.3001 -4.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2502 1.3132 -0.7398 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1283 -2.4373 -0.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6787 -1.7826 0.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3782 0.3298 -1.5446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4015 -1.6075 0.9812 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8821 -0.8480 0.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2233 -2.1216 -0.5887 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5897 1.0632 -1.6905 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9660 1.7477 -1.4547 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0206 1.3098 0.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5287 2.8122 -0.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4230 1.1555 1.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7748 4.2022 1.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8389 2.5103 2.5898 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7890 3.8650 3.3741 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8941 5.3063 1.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4559 4.3581 1.4936 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4249 4.5062 0.0268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0714 -4.6533 -4.6905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4699 -5.6388 -4.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8413 -4.7746 -1.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6305 -1.2055 -5.6816 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1669 -0.7587 -4.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2924 -2.2978 -4.3920 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1010 2.9982 0.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8520 2.1288 1.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4154 2.6418 1.9960 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6351 2.6583 6.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0107 2.3279 5.4909 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5830 1.4311 6.9704 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 13 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 3 27 28 1 0 27 29 1 0 19 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 31 35 1 0 30 36 1 0 10 37 1 0 37 38 1 0 6 39 1 0 2 40 1 0 14 9 1 0 33 18 1 0 34 12 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 0 5 48 1 0 7 49 1 0 8 50 1 0 8 51 1 0 11 52 1 0 15 53 1 0 20 54 1 0 20 55 1 0 21 56 1 0 23 57 1 0 23 58 1 0 23 59 1 0 24 60 1 0 24 61 1 0 25 62 1 0 25 63 1 0 26 64 1 0 28 65 1 0 28 66 1 0 28 67 1 0 29 68 1 0 29 69 1 0 29 70 1 0 32 71 1 0 35 72 1 0 36 73 1 0 38 74 1 0 38 75 1 0 38 76 1 0 39 77 1 0 39 78 1 0 39 79 1 0 40 80 1 0 40 81 1 0 40 82 1 0 M END

Standard InCHIKey	UFSZVMQWXGMGET-HOFJZWJUSA-N
Standard InCHI	InChI=1S/C34H42O6/c1-20(2)10-8-12-22(5)14-16-24-27(39-7)19-29-31(33(24)37)34(38)30-25(32(36)26(35)18-28(30)40-29)17-15-23(6)13-9-11-21(3)4/h10-11,14-15,18-19,35-37H,8-9,12-13,16-17H2,1-7H3/b22-14+,23-15+
SMILES	CC(=CCC/C(=C/Cc1c(cc2c(c1O)c(=O)c1c(C/C=C(C)/CCC=C(C)C)c(c(cc1o2)O)O)OC)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.3	Volume:	594.691 ? Van der Waals volume.
Dense:	0.919	LogP:	9.478 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.501 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.083 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	21.0
TPSA:	100.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.127	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.471	Fsp³:	0.382
MCE-18:	24.0 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.999	Fluc inhibitor:	0.327 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.904 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.791 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.437	Promiscuous compounds:	0.124

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.06	MDCK Permeability:	-4.679
Pgp-inhibitor:	1.0	Pgp-substrate:	0.002
PAMPA:	0.0 ? 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):	0.013
20% Bioavailability (F20%):	0.956	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.787
Plasma Protein Binding (PPB):	97.482%	Volume Distribution (VD):	0.159
Fu:	2.123% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.994
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.998
CYP2C9-inhibitor:	0.813	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.978	CYP2D6-substrate:	0.955
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

7.599

Half-life (T1/2):

1.068

ADMET: Toxicity

hERG Blockers:	0.125	hERG Blockers (10um):	0.676
Human Hepatotoxicity (H-HT):	0.845	Drug-induced Liver Injury (DILI):	0.972
AMES Toxicity:	0.072	Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.683	Skin Sensitization:	0.991
Carcinogencity:	0.376	Eye Corrosion:	0.0
Eye Irritation:	0.418	Respiratory Toxicity:	0.98
Drug-induced Neurotoxicity:	0.155	Ototoxicity:	0.69
Hematotoxicity:	0.385	Drug-induced Nephrotoxicity:	0.269
Genotoxicity:	0.911	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.645	Hek293 Cytotoxicity:	0.516
BCF:	2.046 ? 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:	5.889 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.702 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.814 ? 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
NPO32808	cratoxylum formosum ssp. pruniflorum	Species	Hypericaceae	Eukaryota	stems	n.a.	n.a.	PMID[20608716]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32808	cratoxylum formosum ssp. pruniflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22337	Garcinia dulcis	Species	Clusiaceae	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 NPC150168 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	19674
0.1-0.2	26305
0.2-0.3	3441
0.3-0.4	343
0.4-0.5	56
0.5-0.6	27
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8308	Intermediate Similarity	NPC604618
0.6986	Remote Similarity	NPC236796
0.6533	Remote Similarity	NPC488731
0.6389	Remote Similarity	NPC14353
0.6389	Remote Similarity	NPC56085
0.6154	Remote Similarity	NPC152659
0.6071	Remote Similarity	NPC39091
0.6	Remote Similarity	NPC40491
0.6	Remote Similarity	NPC278052
0.5833	Remote Similarity	NPC7483
0.5833	Remote Similarity	NPC74766
0.5811	Remote Similarity	NPC165977
0.575	Remote Similarity	NPC300727
0.5616	Remote Similarity	NPC142339
0.561	Remote Similarity	NPC239752
0.5513	Remote Similarity	NPC475886
0.5432	Remote Similarity	NPC474287
0.5412	Remote Similarity	NPC479155
0.5366	Remote Similarity	NPC236521
0.5325	Remote Similarity	NPC45146
0.5325	Remote Similarity	NPC266499
0.5316	Remote Similarity	NPC474186
0.5309	Remote Similarity	NPC32694
0.5301	Remote Similarity	NPC474351
0.5294	Remote Similarity	NPC206153
0.5294	Remote Similarity	NPC271629
0.527	Remote Similarity	NPC89474
0.5244	Remote Similarity	NPC475883
0.5244	Remote Similarity	NPC474187
0.5185	Remote Similarity	NPC474350
0.5181	Remote Similarity	NPC262286
0.5169	Remote Similarity	NPC479158
0.5119	Remote Similarity	NPC117854
0.5119	Remote Similarity	NPC170245
0.5063	Remote Similarity	NPC152951
0.506	Remote Similarity	NPC320359

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC150168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3551
0.1-0.2	5533
0.2-0.3	65
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