NPASS Compound

Natural Product: NPC579803

Natural Product ID	NPC579803
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(3~{R},6~{R})-5-hydroxy-6-[[(3~{R},5~{R},10~{S},13~{R},14~{S},17~{R})-14-hydroxy-10,13-dimethyl-17-(5-oxo-2~{H}-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-2-methyl-tetrahydropyran-3-yl] acetate
IUPAC Name	[(3~{R},6~{R})-5-hydroxy-6-[[(3~{R},5~{R},10~{S},13~{R},14~{S},17~{R})-14-hydroxy-10,13-dimethyl-17-(5-oxo-2~{H}-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-methoxy-2-methyl-tetrahydropyran-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 -7.3193 -3.4426 1.3005 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8135 -2.2042 1.6772 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0885 -1.5929 0.6526 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6543 -1.5060 1.1066 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8544 -2.5016 0.5433 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0473 -0.1487 0.8454 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8193 -0.1021 1.5062 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7685 0.1874 0.6017 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8617 -0.9987 0.6003 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5464 -0.7084 0.2158 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7359 0.6358 -0.4369 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0508 0.6215 -1.7864 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1887 0.9415 -0.7126 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7854 0.1137 -1.7793 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1439 -0.4228 -1.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0444 0.4229 -0.6745 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0065 1.2211 -1.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8197 -0.4512 0.2940 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8612 -1.2731 -0.3026 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1776 -1.1027 -0.1115 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9078 -2.0989 -0.8567 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1736 -2.2573 -0.9247 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0131 -2.8987 -1.5201 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7123 -2.4374 -1.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4160 0.6267 1.2058 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1839 1.4489 1.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3610 1.4005 0.2525 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2867 2.6762 -0.2872 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9669 0.8433 0.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3265 1.5729 1.7014 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1685 2.4257 1.2986 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1832 1.7765 0.3614 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1243 1.4650 1.0419 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8719 0.7819 1.4567 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0988 0.9174 0.8917 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0180 1.5049 1.9744 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6798 -0.2829 0.2434 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7930 -0.1112 -1.1494 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9421 -0.0199 -1.8725 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0249 0.1601 -3.3403 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0111 -0.0962 -1.2305 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8686 -3.8554 2.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4813 -4.1577 1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9721 -3.3669 0.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1188 -2.2952 -0.2128 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5727 -1.6613 2.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3883 -2.9649 -0.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8560 0.0534 -0.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2084 0.3002 -0.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9463 -1.5371 1.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3006 -1.7368 -0.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8853 -1.4874 -0.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1849 -0.8501 1.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7530 0.7681 -2.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5051 -0.3220 -1.9598 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6721 1.4481 -1.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1969 2.0274 -1.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1162 -0.7687 -1.9802 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7874 0.7069 -2.7425 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0664 -1.4751 -1.1140 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6437 -0.5253 -2.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4231 1.5225 -2.4421 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2730 2.1517 -1.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8583 0.6237 -1.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1028 -0.9990 0.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6367 -0.3327 0.5094 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2377 -3.3080 -0.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0985 -2.2846 -2.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8786 0.1748 2.0964 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1076 1.2431 0.6115 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6349 0.9718 2.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4301 2.4834 1.8070 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2440 3.3407 0.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1271 -0.2077 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0333 0.8918 2.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0984 2.2576 2.1238 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6008 2.6690 2.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5613 3.3972 0.9333 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0587 2.5849 -0.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8603 2.2798 0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9104 1.4716 2.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0266 1.7395 0.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0681 1.4961 1.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6367 2.4701 2.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9284 0.7969 2.8434 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7627 -0.3254 0.5799 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0863 0.6158 -3.7463 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8718 0.7949 -3.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1489 -0.8064 -3.8750 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 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 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 18 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 6 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 2 0 37 3 1 0 33 8 1 0 32 11 1 0 29 13 1 0 27 16 1 0 24 19 1 0 1 42 1 0 1 43 1 0 1 44 1 0 3 45 1 0 4 46 1 0 5 47 1 0 6 48 1 6 8 49 1 6 9 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 12 55 1 0 12 56 1 0 13 57 1 0 14 58 1 0 14 59 1 0 15 60 1 0 15 61 1 0 17 62 1 0 17 63 1 0 17 64 1 0 18 65 1 1 20 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 28 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 32 79 1 6 33 80 1 0 33 81 1 0 35 82 1 0 36 83 1 0 36 84 1 0 36 85 1 0 37 86 1 1 40 87 1 0 40 88 1 0 40 89 1 0 M END

Standard InCHIKey	WSAWDNPGMCYQEI-TUVPHVQISA-N
Standard InCHI	InChI=1S/C32H48O9/c1-17-27(40-18(2)33)28(37-5)26(35)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h14,17,20-24,26-29,35-36H,6-13,15-16H2,1-5H3/t17?,20-,21-,22-,23?,24?,26?,27-,28?,29+,30+,31-,32+/m1/s1
SMILES	COC1C(O)[C@H](O[C@@H]2CC[C@]3(C)C4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)C4CC[C@@H]3C2)OC(C)[C@H]1OC(C)=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.33	Volume:	581.892 ? Van der Waals volume.
Dense:	0.99	LogP:	2.251 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.706 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.044 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	33.0
TPSA:	120.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.373	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.133	Fsp³:	0.875
MCE-18:	110.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.696	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.089	Promiscuous compounds:	0.099

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.567	MDCK Permeability:	-5.109
Pgp-inhibitor:	0.625	Pgp-substrate:	0.985
PAMPA:	0.973 ? 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):	0.03
20% Bioavailability (F20%):	0.955	30% Bioavailability (F30%):	0.826
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039	MRP1:	0.993
Plasma Protein Binding (PPB):	86.617%	Volume Distribution (VD):	-0.286
Fu:	11.287% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.975
OATP1B3 inhibitor:	0.62	BCRP inhibitor:	0.029
BSEP inhibitor:	0.912

ADMET: Metabolism

CYP1A2-inhibitor:	0.994	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.012
CYP2B6-substrate:	0.375	CYP2C8-inhibitor:	0.091
HLM stability:	0.404 ? 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):

6.56

Half-life (T1/2):

2.082

ADMET: Toxicity

hERG Blockers:	0.319	hERG Blockers (10um):	0.748
Human Hepatotoxicity (H-HT):	0.848	Drug-induced Liver Injury (DILI):	0.627
AMES Toxicity:	0.664	Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.873	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.977
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.787
Hematotoxicity:	0.269	Drug-induced Nephrotoxicity:	0.607
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.711
A549 Cytotoxicity:	0.582	Hek293 Cytotoxicity:	0.985
BCF:	0.568 ? 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:	3.563 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.46 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.637 ? 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
NPO42633	Cerbera floribunda	Species	Apocynaceae	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

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 NPC579803 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	12716
0.1-0.2	31216
0.2-0.3	5541
0.3-0.4	156
0.4-0.5	73
0.5-0.6	82
0.6-0.7	46
0.7-0.8	1
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC486143
0.8095	Intermediate Similarity	NPC486142
0.8095	Intermediate Similarity	NPC486149
0.775	Intermediate Similarity	NPC199428
0.775	Intermediate Similarity	NPC109448
0.775	Intermediate Similarity	NPC310341
0.7561	Intermediate Similarity	NPC93883
0.7556	Intermediate Similarity	NPC486144
0.7556	Intermediate Similarity	NPC486145
0.7556	Intermediate Similarity	NPC486147
0.7556	Intermediate Similarity	NPC486148
0.7204	Intermediate Similarity	NPC120390
0.7176	Intermediate Similarity	NPC72260
0.716	Intermediate Similarity	NPC99620
0.716	Intermediate Similarity	NPC471633
0.7111	Intermediate Similarity	NPC486146
0.7108	Intermediate Similarity	NPC84949
0.7108	Intermediate Similarity	NPC480562
0.7108	Intermediate Similarity	NPC74945
0.7108	Intermediate Similarity	NPC31354
0.7108	Intermediate Similarity	NPC69576
0.7083	Intermediate Similarity	NPC474423
0.7079	Intermediate Similarity	NPC55532
0.7079	Intermediate Similarity	NPC486135
0.7079	Intermediate Similarity	NPC486137
0.7	Intermediate Similarity	NPC232785
0.7	Intermediate Similarity	NPC486139
0.6988	Remote Similarity	NPC5311
0.6941	Remote Similarity	NPC484202
0.6932	Remote Similarity	NPC236973
0.6842	Remote Similarity	NPC475419
0.6778	Remote Similarity	NPC231518
0.6778	Remote Similarity	NPC488944
0.6771	Remote Similarity	NPC486134
0.6771	Remote Similarity	NPC486141
0.6702	Remote Similarity	NPC488943
0.6702	Remote Similarity	NPC488942
0.6667	Remote Similarity	NPC74259
0.6632	Remote Similarity	NPC486136
0.6629	Remote Similarity	NPC30483
0.6629	Remote Similarity	NPC470897
0.6628	Remote Similarity	NPC250556
0.6598	Remote Similarity	NPC474908
0.6552	Remote Similarity	NPC305574
0.6395	Remote Similarity	NPC479356
0.6395	Remote Similarity	NPC479355
0.6374	Remote Similarity	NPC292467
0.6354	Remote Similarity	NPC479360
0.6354	Remote Similarity	NPC479359
0.6333	Remote Similarity	NPC5883
0.63	Remote Similarity	NPC488945
0.63	Remote Similarity	NPC488946
0.6237	Remote Similarity	NPC475629
0.6211	Remote Similarity	NPC329986
0.6211	Remote Similarity	NPC140092
0.6207	Remote Similarity	NPC469750
0.6146	Remote Similarity	NPC486138
0.6146	Remote Similarity	NPC276838
0.6136	Remote Similarity	NPC76572
0.6136	Remote Similarity	NPC193382
0.6129	Remote Similarity	NPC479353
0.6129	Remote Similarity	NPC479354
0.6129	Remote Similarity	NPC486130
0.6122	Remote Similarity	NPC475590
0.6064	Remote Similarity	NPC488941
0.6064	Remote Similarity	NPC488940
0.6064	Remote Similarity	NPC486127
0.6023	Remote Similarity	NPC77299
0.6023	Remote Similarity	NPC480906
0.6022	Remote Similarity	NPC32177
0.6022	Remote Similarity	NPC469756
0.6022	Remote Similarity	NPC275901
0.6	Remote Similarity	NPC483822
0.5978	Remote Similarity	NPC488935
0.5978	Remote Similarity	NPC173555
0.5978	Remote Similarity	NPC488936
0.5957	Remote Similarity	NPC188234
0.5955	Remote Similarity	NPC480914
0.5934	Remote Similarity	NPC193893
0.5882	Remote Similarity	NPC486150
0.5843	Remote Similarity	NPC99080
0.5823	Remote Similarity	NPC268829
0.5823	Remote Similarity	NPC295110
0.5806	Remote Similarity	NPC103534
0.5806	Remote Similarity	NPC44899
0.5806	Remote Similarity	NPC304260
0.5806	Remote Similarity	NPC29639
0.5789	Remote Similarity	NPC480910
0.5789	Remote Similarity	NPC240070
0.5789	Remote Similarity	NPC480909
0.5758	Remote Similarity	NPC479357
0.5758	Remote Similarity	NPC486132
0.5758	Remote Similarity	NPC486131
0.573	Remote Similarity	NPC196429
0.573	Remote Similarity	NPC486129
0.57	Remote Similarity	NPC486128
0.57	Remote Similarity	NPC488938
0.57	Remote Similarity	NPC488937
0.5699	Remote Similarity	NPC480907
0.5667	Remote Similarity	NPC486126
0.5631	Remote Similarity	NPC117445
0.5631	Remote Similarity	NPC308262
0.5618	Remote Similarity	NPC479351
0.5618	Remote Similarity	NPC473852
0.5618	Remote Similarity	NPC479352
0.5514	Remote Similarity	NPC286809
0.551	Remote Similarity	NPC125077
0.5481	Remote Similarity	NPC486140
0.5472	Remote Similarity	NPC488947
0.5444	Remote Similarity	NPC99728
0.5444	Remote Similarity	NPC87250
0.5444	Remote Similarity	NPC244402
0.5444	Remote Similarity	NPC50305
0.5429	Remote Similarity	NPC486133
0.54	Remote Similarity	NPC146857
0.54	Remote Similarity	NPC488939
0.5354	Remote Similarity	NPC208193
0.534	Remote Similarity	NPC329636
0.5333	Remote Similarity	NPC158344
0.5333	Remote Similarity	NPC474418
0.5326	Remote Similarity	NPC6108
0.5326	Remote Similarity	NPC157376
0.5326	Remote Similarity	NPC17896
0.5326	Remote Similarity	NPC469755
0.5326	Remote Similarity	NPC284406
0.5326	Remote Similarity	NPC89514
0.5326	Remote Similarity	NPC34390
0.5326	Remote Similarity	NPC197707
0.5326	Remote Similarity	NPC251866
0.5326	Remote Similarity	NPC142066
0.5326	Remote Similarity	NPC480915
0.5326	Remote Similarity	NPC603972
0.5294	Remote Similarity	NPC475219
0.5217	Remote Similarity	NPC219085
0.5217	Remote Similarity	NPC84987
0.5213	Remote Similarity	NPC180079
0.5204	Remote Similarity	NPC40749
0.5189	Remote Similarity	NPC329675
0.5189	Remote Similarity	NPC194716
0.5182	Remote Similarity	NPC486152
0.5161	Remote Similarity	NPC477580
0.5158	Remote Similarity	NPC179412
0.5158	Remote Similarity	NPC471356
0.5158	Remote Similarity	NPC471353
0.5152	Remote Similarity	NPC32793
0.5152	Remote Similarity	NPC116075
0.5152	Remote Similarity	NPC486151
0.5119	Remote Similarity	NPC222875
0.5119	Remote Similarity	NPC25177
0.5106	Remote Similarity	NPC152615
0.5106	Remote Similarity	NPC10823
0.506	Remote Similarity	NPC187302
0.5054	Remote Similarity	NPC203862
0.5053	Remote Similarity	NPC88668
0.5048	Remote Similarity	NPC479358

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC579803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5629
0.1-0.2	3363
0.2-0.3	142
0.3-0.4	2
0.4-0.5	4
0.5-0.6	4
0.6-0.7	5
0.7-0.8	1
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
0.7176	Intermediate Similarity	NPD8294	Phase 4
0.6889	Remote Similarity	NPD8377	Phase 4
0.6778	Remote Similarity	NPD8033	Approved
0.6628	Remote Similarity	NPD7507	Pre-clinical
0.625	Remote Similarity	NPD8335	Phase 4
0.618	Remote Similarity	NPD8380	Approved
0.5978	Remote Similarity	NPD8296	Phase 4
0.5773	Remote Similarity	NPD8378	Pre-clinical
0.5773	Remote Similarity	NPD8379	Approved
0.5326	Remote Similarity	NPD7319	Approved

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