NPASS Compound

Natural Product: NPC158347

Natural Product ID	NPC158347
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UKMCPHKTWARBEJ-FHUIVYTKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1079242
PubChem CID	23651014
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 89 94 0 0 0 0 0 0 0 0999 V2000 -0.4427 -2.0395 1.9990 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1955 -1.0428 1.4045 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6600 -0.1431 2.1444 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4344 -1.0560 -0.0585 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1246 -2.3231 -0.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3791 -2.3541 0.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3336 -1.2612 0.1642 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7399 -0.2754 -0.7891 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3867 0.0712 -0.4040 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9227 1.2858 -0.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5310 1.5968 0.0252 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4124 0.4350 -0.0859 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1678 -0.7579 -0.7857 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5099 -0.5356 -2.2298 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8260 -1.8819 -0.7463 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1713 -1.4552 -1.3061 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6820 -0.3275 -0.4247 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7813 0.8538 -0.5705 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7781 1.4876 -1.9223 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2623 1.9143 0.4199 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3151 1.3854 1.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5297 0.8775 0.5886 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1316 -0.0784 -0.5189 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6546 0.3704 -1.8336 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8700 -1.3848 -0.1851 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2320 -1.0076 -0.1057 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4910 -0.2442 1.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2992 0.1921 1.5295 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1992 -1.0957 2.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3686 0.9484 0.7216 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6617 0.8630 -1.1163 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4113 1.4069 0.0491 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9228 0.8651 1.3728 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8766 -0.6315 1.4146 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9211 1.1779 -0.0832 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2376 2.9092 0.0806 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5320 -1.8919 -0.5702 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5786 -2.3440 2.9565 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4633 -2.4651 -1.4052 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5226 -3.1995 -0.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0376 -2.2412 1.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8741 -3.3515 0.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6578 -0.8575 -1.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5648 2.1110 -0.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1641 2.4340 -0.6445 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5555 2.0752 1.0253 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5870 0.0883 0.9800 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 -1.4530 -2.5369 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1403 0.3185 -2.4534 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3402 -0.5282 -2.9163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0077 -2.3248 0.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4498 -2.6878 -1.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1694 -1.2221 -2.3670 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8306 -2.3655 -1.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4955 -0.7124 0.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2625 0.8879 -2.7133 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3366 2.4726 -1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7724 1.7504 -2.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7360 2.7844 -0.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4606 2.3399 1.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6861 2.2754 1.9295 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9695 0.6467 2.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1246 1.7153 0.1679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3388 -0.3052 -2.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4992 1.4483 -2.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7817 0.2635 -1.7898 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5051 -1.8376 0.7344 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8423 -2.0819 -1.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8455 -2.1424 2.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1353 -0.6031 3.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2866 -1.1359 1.7713 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1178 1.4792 -0.1982 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2858 1.6689 1.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4429 0.6678 0.6537 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4482 0.4776 -1.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1134 1.6056 -1.7254 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6840 1.1851 2.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9830 1.3618 1.6827 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2719 -0.9362 2.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9024 -1.0373 1.6349 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3309 0.6202 0.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0580 0.5352 -0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4815 2.0923 -0.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8346 3.2480 -0.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1764 3.4370 0.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4842 3.1956 0.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3931 -2.9988 -0.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6194 -1.5305 -1.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4835 -1.6774 -0.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 4 2 1 1 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 8 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 32 36 1 0 7 37 1 6 9 4 1 0 18 12 1 0 28 22 1 0 13 4 1 0 23 17 1 0 34 7 1 0 1 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 6 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 1 14 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 1 19 56 1 0 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 22 63 1 6 24 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 33 77 1 0 33 78 1 0 34 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 36 86 1 0 37 87 1 0 37 88 1 0 37 89 1 0 M END

Standard InCHIKey	UKMCPHKTWARBEJ-FHUIVYTKSA-N
Standard InCHI	InChI=1S/C33H52O4/c1-27(2)15-16-29(5)17-18-33(26(34)35)21(22(29)19-27)9-10-24-30(6)13-12-25-31(7,20-36-28(3,4)37-25)23(30)11-14-32(24,33)8/h9,22-25H,10-20H2,1-8H3,(H,34,35)/t22-,23+,24+,25+,29+,30-,31-,32+,33+/m0/s1
SMILES	OC(=O)[C@@]12CC[C@@]3([C@H](C1=CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]2(C)COC(O1)(C)C)CC(CC3)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.39	Volume:	557.873 ? Van der Waals volume.
Dense:	0.918	LogP:	3.684 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.06 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.405 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	32.0
TPSA:	55.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.362	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.054	Fsp³:	0.909
MCE-18:	121.429 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.775	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.455	Promiscuous compounds:	0.116

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.151	MDCK Permeability:	-4.798
Pgp-inhibitor:	0.318	Pgp-substrate:	0.001
PAMPA:	0.995 ? 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):	0.0
20% Bioavailability (F20%):	0.184	30% Bioavailability (F30%):	0.007
50% Bioavailability (F50%):	0.768

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.703	MRP1:	0.949
Plasma Protein Binding (PPB):	97.59%	Volume Distribution (VD):	-0.384
Fu:	2.85% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.699	BCRP inhibitor:	0.119
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.01	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.24
CYP2C9-inhibitor:	0.009	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.506	CYP3A4-substrate:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.024
HLM stability:	0.767 ? 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):

2.919

Half-life (T1/2):

0.827

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.074
Human Hepatotoxicity (H-HT):	0.887	Drug-induced Liver Injury (DILI):	0.852
AMES Toxicity:	0.368	Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.089	Skin Sensitization:	0.824
Carcinogencity:	0.988	Eye Corrosion:	0.031
Eye Irritation:	0.65	Respiratory Toxicity:	0.89
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.651
Hematotoxicity:	0.169	Drug-induced Nephrotoxicity:	0.413
Genotoxicity:	0.478	RPMI-8226 Immunitoxicity:	0.004
A549 Cytotoxicity:	0.012	Hek293 Cytotoxicity:	0.186
BCF:	2.022 ? 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:	4.393 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.691 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.239 ? 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
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	1
Non-molecular	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
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	150000.0	nM	PMID[25798528]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	150000.0	nM	PMID[19618898]

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 NPC158347 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	27215
0.1-0.2	20184
0.2-0.3	2292
0.3-0.4	136
0.4-0.5	11
0.5-0.6	12
0.6-0.7	7
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
0.6857	Remote Similarity	NPC470590
0.6857	Remote Similarity	NPC285184
0.6429	Remote Similarity	NPC17733
0.6429	Remote Similarity	NPC470629
0.6286	Remote Similarity	NPC251779
0.6164	Remote Similarity	NPC1753
0.6	Remote Similarity	NPC195715
0.5946	Remote Similarity	NPC126369
0.5946	Remote Similarity	NPC470589
0.5946	Remote Similarity	NPC111110
0.5867	Remote Similarity	NPC209868
0.5833	Remote Similarity	NPC199595
0.5769	Remote Similarity	NPC96580
0.5513	Remote Similarity	NPC260149
0.5275	Remote Similarity	NPC469447
0.5128	Remote Similarity	NPC60755
0.5128	Remote Similarity	NPC77099
0.5119	Remote Similarity	NPC478836
0.5065	Remote Similarity	NPC473240

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158347 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6767
0.1-0.2	2353
0.2-0.3	28
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