NPASS Compound

Natural Product: NPC472239

Natural Product ID	NPC472239
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VOYZLKWKVLYJHD-KMWZBSAESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3353859
PubChem CID	n.a.
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 79 82 0 0 0 0 0 0 0 0999 V2000 4.0937 -1.5023 -2.1489 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3014 -0.8467 -1.0046 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8970 -1.2208 -1.2077 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5577 -2.6754 -1.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0288 -2.6945 -1.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3754 -1.2363 -0.9708 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8729 -0.6733 -0.2634 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8996 -1.3346 1.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8081 0.7932 -0.1406 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5796 1.3529 -0.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5712 0.3763 0.5544 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5168 -0.9536 -0.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4798 -1.8166 0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5609 -1.3712 1.0946 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9881 -0.0189 0.5167 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9150 1.0052 0.6433 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9954 1.7984 1.9294 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1787 2.0343 -0.4674 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6120 2.4470 -0.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3495 1.9308 0.7833 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9421 2.6088 1.5902 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3368 0.4268 0.9617 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7395 0.0088 2.3298 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4185 -0.0695 -0.0028 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5406 -0.7273 -2.3561 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9540 -1.2381 0.2570 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4142 -0.7307 0.2091 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5038 0.7119 0.0711 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0582 1.4681 0.9706 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6654 1.0720 2.2203 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1626 2.0013 2.9671 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7870 -0.1983 2.7345 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0785 2.9635 0.6868 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9008 -0.8346 -2.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5908 -2.4192 -1.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4478 -1.7219 -3.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3915 0.2463 -1.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6070 -0.8437 -2.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7766 -3.0952 -2.2249 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0830 -3.2951 -0.4819 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4542 -3.1579 -1.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2519 -3.2671 -0.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0720 -1.8604 1.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6408 -2.1708 1.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0412 -0.6115 1.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4455 1.0973 0.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3396 1.2488 -1.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8558 1.8038 -0.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5194 2.2040 0.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2181 0.2003 1.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4734 -2.7884 -0.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2105 -1.2728 2.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4444 -2.0123 1.0777 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0828 -0.2185 -0.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7061 1.4154 2.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9943 1.7918 2.4468 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2145 2.8740 1.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5595 2.9289 -0.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9511 1.5786 -1.4295 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1359 2.1610 -1.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7291 3.5700 -0.3612 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6509 -0.6175 2.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9868 -0.5932 2.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0381 0.9215 2.8947 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3623 -1.1483 -0.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3874 0.1613 0.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3929 0.4995 -0.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6486 -0.5934 -2.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0824 0.2292 -2.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2434 -1.5041 -3.1068 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5468 -0.7497 1.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0501 -2.3386 0.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8886 -1.1781 -0.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9283 -1.1122 1.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1042 1.2376 -0.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6743 -0.4321 3.1979 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0842 3.5331 1.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1672 3.2382 0.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9744 3.2046 0.0857 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 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 22 24 1 0 6 25 1 6 2 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 29 33 1 0 7 3 1 0 16 11 1 0 12 6 1 0 22 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 6 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 1 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 6 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 28 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 M END

Standard InCHIKey	VOYZLKWKVLYJHD-KMWZBSAESA-N
Standard InCHI	InChI=1S/C30H46O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h10-11,19,21-22,24H,8-9,12-18H2,1-7H3,(H,32,33)/b20-10-/t19-,21-,22-,24+,28-,29-,30+/m1/s1
SMILES	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)CC/C=C(C(=O)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	509.035 ? Van der Waals volume.
Dense:	0.893	LogP:	5.359 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.985 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.264 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.343	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.625	Fsp³:	0.8
MCE-18:	80.593 ? 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:	0.925	Fluc inhibitor:	0.001 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.63	Promiscuous compounds:	0.154

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.05	MDCK Permeability:	-4.886
Pgp-inhibitor:	0.355	Pgp-substrate:	0.0
PAMPA:	0.666 ? 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%):	0.075	30% Bioavailability (F30%):	0.18
50% Bioavailability (F50%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.954
Plasma Protein Binding (PPB):	94.091%	Volume Distribution (VD):	-0.273
Fu:	6.241% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.014
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.045	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.896	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.951
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
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):

4.346

Half-life (T1/2):

0.634

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.086
Human Hepatotoxicity (H-HT):	0.67	Drug-induced Liver Injury (DILI):	0.77
AMES Toxicity:	0.091	Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.36	Skin Sensitization:	0.886
Carcinogencity:	0.453	Eye Corrosion:	0.174
Eye Irritation:	0.637	Respiratory Toxicity:	0.671
Drug-induced Neurotoxicity:	0.336	Ototoxicity:	0.556
Hematotoxicity:	0.684	Drug-induced Nephrotoxicity:	0.808
Genotoxicity:	0.746	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.028	Hek293 Cytotoxicity:	0.101
BCF:	1.348 ? 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:	4.275 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.628 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.062 ? 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
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]
NPO33399	abies faxoniana	Species	Pinaceae	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

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell line	2
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
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	24000.0	nM	PMID[20479200]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[25554367]

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 NPC472239 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	27294
0.1-0.2	18781
0.2-0.3	3109
0.3-0.4	488
0.4-0.5	124
0.5-0.6	37
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	0

Similarity Score	Similarity Level	Natural Product ID
0.7692	Intermediate Similarity	NPC6190
0.7353	Intermediate Similarity	NPC73506
0.7313	Intermediate Similarity	NPC293081
0.7015	Intermediate Similarity	NPC472240
0.7015	Intermediate Similarity	NPC262858
0.6667	Remote Similarity	NPC260992
0.6562	Remote Similarity	NPC470078
0.6471	Remote Similarity	NPC483383
0.6377	Remote Similarity	NPC479296
0.6377	Remote Similarity	NPC87552
0.6324	Remote Similarity	NPC142253
0.6324	Remote Similarity	NPC3511
0.6232	Remote Similarity	NPC147066
0.6176	Remote Similarity	NPC90652
0.6176	Remote Similarity	NPC155255
0.6176	Remote Similarity	NPC470052
0.6143	Remote Similarity	NPC471224
0.6143	Remote Similarity	NPC8571
0.6119	Remote Similarity	NPC470223
0.6087	Remote Similarity	NPC470047
0.6087	Remote Similarity	NPC470046
0.5915	Remote Similarity	NPC486521
0.5915	Remote Similarity	NPC262870
0.5811	Remote Similarity	NPC489798
0.5775	Remote Similarity	NPC162703
0.5753	Remote Similarity	NPC479667
0.5733	Remote Similarity	NPC489789
0.5714	Remote Similarity	NPC470417
0.5694	Remote Similarity	NPC146554
0.5652	Remote Similarity	NPC16287
0.5526	Remote Similarity	NPC479301
0.5507	Remote Similarity	NPC247220
0.5467	Remote Similarity	NPC456
0.5467	Remote Similarity	NPC472941
0.5467	Remote Similarity	NPC483394
0.5467	Remote Similarity	NPC202814
0.5443	Remote Similarity	NPC484792
0.5405	Remote Similarity	NPC470050
0.5405	Remote Similarity	NPC67831
0.5405	Remote Similarity	NPC174051
0.5405	Remote Similarity	NPC470051
0.5352	Remote Similarity	NPC82902
0.5333	Remote Similarity	NPC605437
0.525	Remote Similarity	NPC189282
0.525	Remote Similarity	NPC237402
0.5195	Remote Similarity	NPC273669
0.5195	Remote Similarity	NPC484802
0.5195	Remote Similarity	NPC118647
0.519	Remote Similarity	NPC63023
0.519	Remote Similarity	NPC121566
0.519	Remote Similarity	NPC100955
0.519	Remote Similarity	NPC95243
0.5128	Remote Similarity	NPC285702
0.5128	Remote Similarity	NPC166745
0.5128	Remote Similarity	NPC235464
0.5068	Remote Similarity	NPC477372
0.5067	Remote Similarity	NPC263272
0.5065	Remote Similarity	NPC96496

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6753
0.1-0.2	2300
0.2-0.3	92
0.3-0.4	5
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