NPASS Compound

Natural Product: NPC331618

Natural Product ID	NPC331618
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MHGLNDDJLDJDBG-GSYFYXRESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL485990
PubChem CID	11419367
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

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 3.3397 -0.6142 2.3495 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2947 -1.2562 1.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2755 -0.5602 0.1063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6542 -0.7090 0.7441 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7047 -0.0559 -0.0777 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5899 1.3898 -0.2581 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8322 2.1844 0.4700 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4697 2.0186 -1.3113 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7899 -0.6346 -1.3525 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9946 -1.5733 0.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1885 -2.5463 1.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1839 -2.4686 0.7218 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1357 -1.3916 -0.3795 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9832 -0.5326 0.1478 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4858 0.1894 1.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8026 0.9259 1.1518 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9203 0.0738 0.6417 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4857 -0.8198 -0.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8261 -0.1088 -1.7594 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3628 -0.1991 -1.8516 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8844 0.7339 -0.8086 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1841 0.7560 0.4794 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0736 -0.3259 1.4483 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4684 2.1191 1.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9633 2.1571 1.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6725 0.9132 0.9024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3720 0.5764 -0.5484 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8032 -0.8048 -0.8932 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1926 1.5432 -1.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0479 1.1846 0.9598 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5113 0.4084 -0.9090 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2070 -2.1185 -1.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4856 -0.8387 3.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2154 -1.0095 2.9119 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5333 0.4986 2.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7810 -2.2824 1.1565 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0913 0.4866 -0.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2480 -1.1664 -0.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6363 -0.1964 1.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9056 -1.7661 0.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7057 -0.2822 0.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8385 3.2597 0.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2200 1.8644 1.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5084 1.7142 -1.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1740 1.5808 -2.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3075 3.0968 -1.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8400 -1.6288 -1.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1858 -2.1330 -0.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6109 -3.5833 1.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2686 -2.3298 2.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5414 -3.4312 0.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8766 -2.1051 1.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2913 -0.5533 2.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2295 0.9690 1.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6432 1.7673 0.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0901 1.3605 2.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1650 -1.7348 -0.4677 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4044 -0.5347 -2.6602 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6525 1.0063 -1.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6873 -1.2421 -1.7389 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6276 0.1752 -2.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7883 1.7712 -1.2591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0228 -0.1130 2.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5190 -1.3265 1.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8935 2.2994 2.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2578 2.8934 0.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0986 2.2079 2.4697 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4397 3.0682 0.9594 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5049 0.0549 1.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8871 -0.9494 -0.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7172 -0.9062 -2.0154 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2190 -1.6099 -0.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9780 1.0341 -1.9606 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6208 2.3673 -0.7828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4767 2.0441 -2.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5404 0.7741 0.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8920 1.3402 -0.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7142 0.7537 -1.5997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2799 -0.0385 -1.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7463 -2.3971 -2.1851 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8143 -1.5562 -2.3529 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6792 -3.1277 -1.4505 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 2 0 6 8 1 0 5 9 1 0 2 10 1 0 10 11 1 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 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 26 30 1 0 14 31 1 0 13 32 1 0 14 10 1 0 18 13 1 0 22 17 1 0 23 17 1 0 27 21 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	MHGLNDDJLDJDBG-GSYFYXRESA-N
Standard InCHI	InChI=1S/C30H50O2/c1-19(2)22(31)9-8-20(3)21-12-14-28(7)24-11-10-23-26(4,5)25(32)13-15-29(23)18-30(24,29)17-16-27(21,28)6/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21-,22?,23+,24+,25+,27-,28+,29-,30+/m1/s1
SMILES	CC(CCC(C(=C)C)O)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	6.067 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.985 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.413 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.444	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.572	Fsp³:	0.933
MCE-18:	133.966 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.367	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.531	Promiscuous compounds:	0.026

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.961	MDCK Permeability:	-4.731
Pgp-inhibitor:	0.001	Pgp-substrate:	0.121
PAMPA:	0.314 ? 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):	0.004
20% Bioavailability (F20%):	0.078	30% Bioavailability (F30%):	0.404
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838	MRP1:	0.997
Plasma Protein Binding (PPB):	85.731%	Volume Distribution (VD):	-0.024
Fu:	11.229% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.019
OATP1B3 inhibitor:	0.969	BCRP inhibitor:	0.1
BSEP inhibitor:	0.406

ADMET: Metabolism

CYP1A2-inhibitor:	0.144	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.279
CYP2C9-inhibitor:	0.765	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.996	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.934	CYP3A4-substrate:	0.118
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.956
HLM stability:	0.997 ? 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):

19.657

Half-life (T1/2):

1.235

ADMET: Toxicity

hERG Blockers:	0.366	hERG Blockers (10um):	0.745
Human Hepatotoxicity (H-HT):	0.58	Drug-induced Liver Injury (DILI):	0.015
AMES Toxicity:	0.124	Rat Oral Acute Toxicity:	0.191
Maximum Recommended Daily Dose:	0.738	Skin Sensitization:	0.203
Carcinogencity:	0.342	Eye Corrosion:	0.005
Eye Irritation:	0.319	Respiratory Toxicity:	0.713
Drug-induced Neurotoxicity:	0.238	Ototoxicity:	0.909
Hematotoxicity:	0.104	Drug-induced Nephrotoxicity:	0.131
Genotoxicity:	0.006	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.205	Hek293 Cytotoxicity:	0.344
BCF:	1.866 ? 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:	5.229 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.488 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.716 ? 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
NPO33470	clermontia fauerei	Species	Campanulaceae	Eukaryota	leaves,?twigs	island of Kauai, Hawaii, USA	n.a.	PMID[16124770]
NPO33470	clermontia fauerei	Species	Campanulaceae	Eukaryota	whole?plant	USA	n.a.	PMID[16124770]

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 NPC331618 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	28112
0.1-0.2	18904
0.2-0.3	2370
0.3-0.4	321
0.4-0.5	98
0.5-0.6	22
0.6-0.7	16
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC257191
0.7872	Intermediate Similarity	NPC196358
0.7708	Intermediate Similarity	NPC200243
0.7708	Intermediate Similarity	NPC254509
0.766	Intermediate Similarity	NPC299948
0.766	Intermediate Similarity	NPC241085
0.766	Intermediate Similarity	NPC607543
0.7551	Intermediate Similarity	NPC472342
0.7447	Intermediate Similarity	NPC41577
0.7347	Intermediate Similarity	NPC85346
0.7347	Intermediate Similarity	NPC65897
0.7347	Intermediate Similarity	NPC80237
0.7255	Intermediate Similarity	NPC76518
0.72	Intermediate Similarity	NPC479659
0.7	Intermediate Similarity	NPC604180
0.6981	Remote Similarity	NPC89747
0.6863	Remote Similarity	NPC470830
0.6863	Remote Similarity	NPC195530
0.6863	Remote Similarity	NPC273366
0.6792	Remote Similarity	NPC477858
0.6667	Remote Similarity	NPC82623
0.6607	Remote Similarity	NPC483817
0.6604	Remote Similarity	NPC472341
0.6415	Remote Similarity	NPC70982
0.6415	Remote Similarity	NPC22133
0.6364	Remote Similarity	NPC473238
0.6296	Remote Similarity	NPC67872
0.614	Remote Similarity	NPC18384
0.614	Remote Similarity	NPC110923
0.614	Remote Similarity	NPC74296
0.6071	Remote Similarity	NPC134481
0.5932	Remote Similarity	NPC195366
0.5932	Remote Similarity	NPC114743
0.5926	Remote Similarity	NPC145552
0.5893	Remote Similarity	NPC12722
0.5818	Remote Similarity	NPC473279
0.5818	Remote Similarity	NPC49168
0.5818	Remote Similarity	NPC5046
0.5667	Remote Similarity	NPC85379
0.5667	Remote Similarity	NPC144909
0.5667	Remote Similarity	NPC476304
0.5614	Remote Similarity	NPC195489
0.5593	Remote Similarity	NPC476186
0.5556	Remote Similarity	NPC611460
0.5536	Remote Similarity	NPC302041
0.5517	Remote Similarity	NPC606508
0.55	Remote Similarity	NPC307776
0.5439	Remote Similarity	NPC113978
0.5357	Remote Similarity	NPC69149
0.5172	Remote Similarity	NPC282275
0.5172	Remote Similarity	NPC484086
0.5079	Remote Similarity	NPC488282
0.5079	Remote Similarity	NPC488286

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC331618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8231
0.1-0.2	868
0.2-0.3	50
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