NPASS Compound

Natural Product: NPC474889

Natural Product ID	NPC474889
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Acetyl Eburicoic Acid
IUPAC Name	(2R)-2-[(3S,5R,10S,13R,14R,17R)-3-acetyloxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	Acetyl Eburicoic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL486258
PubChem CID	44575769
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 92 0 0 0 0 0 0 0 0999 V2000 -8.9229 1.4232 0.8515 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6085 0.7137 0.9572 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7420 -0.3891 1.9923 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2494 0.1571 -0.3800 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0427 0.3419 -1.4169 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9785 -0.6203 -0.5565 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8213 0.3064 -0.1836 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5078 -0.5084 -0.3693 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4017 0.4091 -0.0021 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 1.6644 -0.8586 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9326 1.8960 -1.2489 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3682 0.4922 -1.1545 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0161 -0.1313 0.0349 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3973 0.2172 1.3641 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8138 1.0991 1.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6671 0.7343 0.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1046 0.4404 -1.0472 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8911 0.0529 -2.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2583 -0.4545 -2.0165 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5530 -0.5705 -0.5400 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1506 0.6843 0.1658 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6796 0.7043 1.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1720 0.7144 1.5273 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7686 0.0875 0.3170 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9282 -1.0465 -0.2445 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6428 -1.6362 -1.4356 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9034 -2.1252 0.8292 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0512 -0.4336 0.7024 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2213 -0.0821 0.0872 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1887 0.7379 -0.8658 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5558 -0.6112 0.4728 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6409 1.9591 -0.4875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9274 -1.6564 -0.0468 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7931 -0.1685 -2.4543 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6742 -1.6340 0.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7868 -2.8425 0.2696 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7119 -1.3549 1.9707 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1615 1.7919 1.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7019 0.6987 0.5369 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8137 2.2622 0.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8317 1.4385 1.2322 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7108 -0.9121 1.8957 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9374 -1.1231 1.9137 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7602 0.1162 2.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9720 0.8940 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7760 -0.0670 -2.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9121 -0.9171 -1.5994 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9301 -1.4659 0.1528 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8506 1.1374 -0.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9135 0.6851 0.8297 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5469 -0.8984 -1.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6671 0.7986 1.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8091 2.5486 -0.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0233 1.4702 -1.7340 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4075 2.6582 -0.7006 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9650 2.2381 -2.3255 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1324 0.7767 1.9802 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1492 -0.6781 1.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6113 2.1815 1.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4444 0.8702 2.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3174 -0.8137 -2.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8574 0.8422 -3.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0370 0.1372 -2.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4255 -1.5009 -2.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8409 -1.3706 -0.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3588 1.6921 2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3476 -0.1328 2.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5687 0.1917 2.4474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6093 1.7521 1.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9702 0.7719 -0.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6361 -2.0017 -1.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1095 -2.5393 -1.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8327 -0.9338 -2.2414 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8307 -2.3296 1.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4206 -1.8360 1.7436 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2967 -3.0892 0.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2606 0.2463 0.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8882 -1.3170 -0.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5406 -1.0823 1.4713 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 2.7275 -0.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4200 2.4848 0.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0545 1.8444 -1.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1714 -1.8596 -0.0733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2767 -2.0557 0.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4708 -2.0892 -0.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6275 -1.2344 -2.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8606 0.1197 -2.7027 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2175 0.3259 -3.2624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1759 -2.0246 2.5697 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 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 2 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 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 21 32 1 0 13 33 1 0 12 34 1 0 8 35 1 0 35 36 2 0 35 37 1 0 13 9 1 0 17 12 1 0 21 16 1 0 25 20 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 3 42 1 0 3 43 1 0 3 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 9 52 1 0 10 53 1 0 10 54 1 0 11 55 1 0 11 56 1 0 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 20 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 24 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 27 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 33 83 1 0 33 84 1 0 33 85 1 0 34 86 1 0 34 87 1 0 34 88 1 0 37 89 1 0 M END

Standard InCHIKey	IMWCOHWUNCFQDX-DLCVLMBDSA-N
Standard InCHI	InChI=1S/C33H52O4/c1-20(2)21(3)10-11-23(29(35)36)24-14-18-33(9)26-12-13-27-30(5,6)28(37-22(4)34)16-17-31(27,7)25(26)15-19-32(24,33)8/h20,23-24,27-28H,3,10-19H2,1-2,4-9H3,(H,35,36)/t23-,24-,27+,28+,31-,32-,33+/m1/s1
SMILES	CC(C)C(=C)CCC(C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)OC(=O)C)C)C)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.39	Volume:	569.713 ? Van der Waals volume.
Dense:	0.899	LogP:	5.061 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.72 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.409 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	23.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.275	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.804	Fsp³:	0.818
MCE-18:	85.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.481	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.08 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.441	Promiscuous compounds:	0.012

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.022	MDCK Permeability:	-4.708
Pgp-inhibitor:	0.688	Pgp-substrate:	0.0
PAMPA:	0.011 ? 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%):	0.018	30% Bioavailability (F30%):	0.227
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	1.0
Plasma Protein Binding (PPB):	96.031%	Volume Distribution (VD):	-0.098
Fu:	4.633% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.865
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.003
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.071	CYP3A4-substrate:	0.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.543
HLM stability:	0.987 ? 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):

3.437

Half-life (T1/2):

0.69

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.238
Human Hepatotoxicity (H-HT):	0.553	Drug-induced Liver Injury (DILI):	0.157
AMES Toxicity:	0.036	Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.635	Skin Sensitization:	0.258
Carcinogencity:	0.205	Eye Corrosion:	0.018
Eye Irritation:	0.667	Respiratory Toxicity:	0.476
Drug-induced Neurotoxicity:	0.19	Ototoxicity:	0.812
Hematotoxicity:	0.226	Drug-induced Nephrotoxicity:	0.224
Genotoxicity:	0.006	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.029	Hek293 Cytotoxicity:	0.068
BCF:	1.712 ? 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:	4.925 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.322 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.499 ? 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
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620242]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19842686]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8498	Laetiporus sulphureus	Species	Coriolaceae	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

Activity Type	# Activity
IC50	2
FC	1

Activity Type	# Activity
Cell line	3

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	15000.0	nM	PMID[9548852]
NPT116	Cell line	HL-60	Homo sapiens	FC	=	7.0	n.a.	PMID[18364258]

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 NPC474889 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	23399
0.1-0.2	23671
0.2-0.3	2496
0.3-0.4	228
0.4-0.5	36
0.5-0.6	20
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	Natural Product ID
0.7937	Intermediate Similarity	NPC148414
0.7937	Intermediate Similarity	NPC111585
0.7937	Intermediate Similarity	NPC175628
0.7313	Intermediate Similarity	NPC184848
0.6769	Remote Similarity	NPC55309
0.6769	Remote Similarity	NPC28252
0.6429	Remote Similarity	NPC484973
0.6111	Remote Similarity	NPC69548
0.5942	Remote Similarity	NPC482908
0.589	Remote Similarity	NPC42042
0.5714	Remote Similarity	NPC469400
0.5513	Remote Similarity	NPC473514
0.5455	Remote Similarity	NPC473648
0.5405	Remote Similarity	NPC608955
0.5325	Remote Similarity	NPC288464
0.5325	Remote Similarity	NPC477813
0.5325	Remote Similarity	NPC607198
0.5278	Remote Similarity	NPC473269
0.5278	Remote Similarity	NPC233836
0.5278	Remote Similarity	NPC159046
0.5278	Remote Similarity	NPC187376
0.5139	Remote Similarity	NPC201912
0.5139	Remote Similarity	NPC38350
0.5139	Remote Similarity	NPC601139
0.5132	Remote Similarity	NPC471896
0.5122	Remote Similarity	NPC195708
0.5068	Remote Similarity	NPC48330
0.5068	Remote Similarity	NPC23434

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6380
0.1-0.2	2713
0.2-0.3	54
0.3-0.4	3
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