NPASS Compound

Natural Product: NPC281563

Natural Product ID	NPC281563
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pescaproside A
IUPAC Name	methyl (11S)-11-[(2R,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5S,6S)-3-dodecanoyloxy-6-methyl-4,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxyhexadecanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510033
PubChem CID	21575465
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 189193 0 0 0 0 0 0 0 0999 V2000 16.6983 11.0571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5493 10.0930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4002 9.1288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2511 8.1646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1021 7.2004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9530 6.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8039 5.2721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6549 4.3079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5058 3.3437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3567 2.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2077 1.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 -1.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -4.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -6.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0481 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 -7.6590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -7.6590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 -5.2176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -6.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -4.7665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 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0 80 74 1 0 1 84 1 0 1 85 1 0 1 86 1 0 2 87 1 0 2 88 1 0 3 89 1 0 3 90 1 0 4 91 1 0 4 92 1 0 5 93 1 0 5 94 1 0 6 95 1 0 6 96 1 0 7 97 1 0 7 98 1 0 8 99 1 0 8100 1 0 9101 1 0 9102 1 0 10103 1 0 10104 1 0 11105 1 0 11106 1 0 15107 1 1 16108 1 1 17109 1 6 18110 1 1 19111 1 0 19112 1 0 19113 1 0 21114 1 6 23115 1 1 24116 1 6 25117 1 0 25118 1 0 25119 1 0 27120 1 1 28121 1 6 29122 1 6 30123 1 0 31124 1 0 33125 1 1 34126 1 6 35127 1 6 36128 1 6 37129 1 0 37130 1 0 37131 1 0 39132 1 6 41133 1 1 42134 1 0 42135 1 0 43136 1 0 43137 1 0 44138 1 0 44139 1 0 45140 1 0 45141 1 0 46142 1 0 46143 1 0 46144 1 0 47145 1 0 47146 1 0 48147 1 0 48148 1 0 49149 1 0 49150 1 0 50151 1 0 50152 1 0 51153 1 0 51154 1 0 52155 1 0 52156 1 0 53157 1 0 53158 1 0 54159 1 0 54160 1 0 55161 1 0 55162 1 0 59163 1 0 59164 1 0 59165 1 0 60166 1 0 61167 1 0 63168 1 6 64169 1 1 65170 1 1 66171 1 6 67172 1 1 68173 1 0 68174 1 0 68175 1 0 70176 1 0 71177 1 0 72178 1 0 74179 1 6 75180 1 1 76181 1 1 77182 1 6 78183 1 1 79184 1 0 79185 1 0 79186 1 0 81187 1 0 82188 1 0 83189 1 0 M END

Standard InCHIKey	MHVINGJQHVKKSE-RVBJTDSWSA-N
Standard InCHI	InChI=1S/C59H106O24/c1-9-11-13-14-15-16-19-23-27-31-39(61)79-54-53(83-56-48(70)44(66)41(63)33(4)74-56)51(81-55-47(69)43(65)40(62)32(3)73-55)36(7)77-59(54)80-50-35(6)76-57(49(71)46(50)68)82-52-45(67)42(64)34(5)75-58(52)78-37(28-24-12-10-2)29-25-21-18-17-20-22-26-30-38(60)72-8/h32-37,40-59,62-71H,9-31H2,1-8H3/t32-,33-,34+,35-,36-,37-,40-,41-,42-,43+,44+,45-,46-,47+,48+,49+,50-,51-,52+,53+,54+,55-,56-,57-,58-,59-/m0/s1
SMILES	CCCCCCCCCCCC(=O)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1O[C@H]1[C@H](C)O[C@H]([C@@H]([C@@H]1O)O)O[C@@H]1[C@H]([C@H]([C@@H](C)O[C@H]1O[C@@H](CCCCC)CCCCCCCCCC(=O)OC)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1198.71	Volume:	1191.93 ? Van der Waals volume.
Dense:	1.006	LogP:	4.294 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.655 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.166 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	37.0	Rigid Bonds:	32.0
TPSA:	347.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.032	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.413	Fsp³:	0.966
MCE-18:	104.534 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.98	Fluc inhibitor:	0.334 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.5	Promiscuous compounds:	0.023

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.434	MDCK Permeability:	-5.011
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
PAMPA:	1.0 ? 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):	0.988
20% Bioavailability (F20%):	0.982	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	93.215%	Volume Distribution (VD):	-0.228
Fu:	5.652% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.939
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.006

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.003 ? 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):

1.127

Half-life (T1/2):

2.979

ADMET: Toxicity

hERG Blockers:	0.103	hERG Blockers (10um):	0.636
Human Hepatotoxicity (H-HT):	0.073	Drug-induced Liver Injury (DILI):	0.735
AMES Toxicity:	0.498	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.346	Drug-induced Nephrotoxicity:	0.804
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.359
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.164
BCF:	1.838 ? 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:	6.036 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.953 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.067 ? 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
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730248]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	Leaves	Khon Kaen, Thailand	2002-APR	PMID[15921434]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	ground entire plants	Hainan Province, China	2004-APR	PMID[19061389]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21338052]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31017778]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23352	Ipomoea pes-caprae	Species	Convolvulaceae	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
ED50	4

Activity Type	# Activity
Non-molecular	4

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	5.0	ug ml-1	PMID[15730248]

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 NPC281563 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	21477
0.1-0.2	24495
0.2-0.3	3552
0.3-0.4	195
0.4-0.5	30
0.5-0.6	35
0.6-0.7	48
0.7-0.8	0
0.8-0.85	6
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC600446
0.9296	High Similarity	NPC605013
0.8356	Intermediate Similarity	NPC113745
0.8356	Intermediate Similarity	NPC477320
0.8356	Intermediate Similarity	NPC477323
0.8356	Intermediate Similarity	NPC477325
0.8356	Intermediate Similarity	NPC609436
0.8056	Intermediate Similarity	NPC146380
0.7887	Intermediate Similarity	NPC606819
0.7821	Intermediate Similarity	NPC267592
0.7625	Intermediate Similarity	NPC307400
0.7625	Intermediate Similarity	NPC27289
0.7564	Intermediate Similarity	NPC477326
0.7532	Intermediate Similarity	NPC604005
0.7532	Intermediate Similarity	NPC605014
0.75	Intermediate Similarity	NPC477319
0.7468	Intermediate Similarity	NPC109887
0.7432	Intermediate Similarity	NPC477350
0.7407	Intermediate Similarity	NPC143421
0.7407	Intermediate Similarity	NPC119583
0.7317	Intermediate Similarity	NPC483170
0.7262	Intermediate Similarity	NPC123204
0.7229	Intermediate Similarity	NPC290012
0.7229	Intermediate Similarity	NPC115013
0.7215	Intermediate Similarity	NPC89843
0.6941	Remote Similarity	NPC183888
0.6941	Remote Similarity	NPC259294
0.6824	Remote Similarity	NPC169345
0.6786	Remote Similarity	NPC472204
0.675	Remote Similarity	NPC22742
0.675	Remote Similarity	NPC477349
0.675	Remote Similarity	NPC477346
0.6744	Remote Similarity	NPC184915
0.6744	Remote Similarity	NPC224953
0.6744	Remote Similarity	NPC126685
0.6707	Remote Similarity	NPC477344
0.6667	Remote Similarity	NPC472205
0.6628	Remote Similarity	NPC477317
0.6628	Remote Similarity	NPC477318
0.6591	Remote Similarity	NPC44782
0.6585	Remote Similarity	NPC478734
0.6494	Remote Similarity	NPC478729
0.6429	Remote Similarity	NPC478733
0.6353	Remote Similarity	NPC146992
0.6353	Remote Similarity	NPC85759
0.6296	Remote Similarity	NPC477329
0.6279	Remote Similarity	NPC297768
0.6279	Remote Similarity	NPC173328
0.6277	Remote Similarity	NPC124878
0.6277	Remote Similarity	NPC231888
0.625	Remote Similarity	NPC478731
0.6211	Remote Similarity	NPC35338
0.6211	Remote Similarity	NPC204214
0.6211	Remote Similarity	NPC92283
0.6207	Remote Similarity	NPC294748
0.6207	Remote Similarity	NPC478730
0.6207	Remote Similarity	NPC186992
0.6173	Remote Similarity	NPC477328
0.6173	Remote Similarity	NPC477330
0.6136	Remote Similarity	NPC238264
0.6136	Remote Similarity	NPC476087
0.6136	Remote Similarity	NPC475667
0.6136	Remote Similarity	NPC477345
0.6122	Remote Similarity	NPC10121
0.6122	Remote Similarity	NPC198918
0.6122	Remote Similarity	NPC10883
0.6118	Remote Similarity	NPC158302
0.6111	Remote Similarity	NPC163409
0.6067	Remote Similarity	NPC238056
0.6067	Remote Similarity	NPC478732
0.6042	Remote Similarity	NPC63404
0.6	Remote Similarity	NPC475270
0.6	Remote Similarity	NPC475327
0.5979	Remote Similarity	NPC28069
0.5979	Remote Similarity	NPC77651
0.5934	Remote Similarity	NPC472200
0.5934	Remote Similarity	NPC475525
0.5934	Remote Similarity	NPC475540
0.593	Remote Similarity	NPC479059
0.587	Remote Similarity	NPC476066
0.5814	Remote Similarity	NPC477331
0.5814	Remote Similarity	NPC477332
0.5806	Remote Similarity	NPC475164
0.5745	Remote Similarity	NPC473605
0.5745	Remote Similarity	NPC475375
0.5686	Remote Similarity	NPC471025
0.5663	Remote Similarity	NPC475425
0.5644	Remote Similarity	NPC290276
0.5638	Remote Similarity	NPC478728
0.5625	Remote Similarity	NPC475241
0.5618	Remote Similarity	NPC479061
0.5586	Remote Similarity	NPC147032
0.5579	Remote Similarity	NPC478727
0.5556	Remote Similarity	NPC479058
0.5556	Remote Similarity	NPC478724
0.5556	Remote Similarity	NPC479060
0.5532	Remote Similarity	NPC269318
0.5444	Remote Similarity	NPC478722
0.5444	Remote Similarity	NPC60849
0.5444	Remote Similarity	NPC478725
0.5385	Remote Similarity	NPC478723
0.5385	Remote Similarity	NPC44682
0.537	Remote Similarity	NPC471024
0.5327	Remote Similarity	NPC471026
0.5269	Remote Similarity	NPC478726
0.5185	Remote Similarity	NPC472352
0.5181	Remote Similarity	NPC169085
0.5135	Remote Similarity	NPC206823

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC281563 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7275
0.1-0.2	1788
0.2-0.3	85
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