NPASS Compound

Natural Product: NPC212729

Natural Product ID	NPC212729
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Helicide
IUPAC Name	4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
Synonyms	Helicide
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL201358
PubChem CID	12896796
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

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 36 37 0 0 0 0 0 0 0 0999 V2000 -3.2004 -2.5738 0.3421 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2657 -1.6601 1.4093 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5517 -0.3975 0.9365 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2470 -0.7748 0.6399 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4174 0.3092 0.3647 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6067 -0.1675 -0.4605 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9457 -0.1929 -0.2516 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 0.2956 0.9077 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8550 0.2643 1.1089 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7100 -0.2512 0.1668 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1391 -0.7352 -0.9879 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7858 -0.7178 -1.2169 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1638 -0.2891 0.3712 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6388 0.1589 1.4290 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1425 1.3866 -0.4157 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2048 0.7177 -1.2513 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2530 0.1923 -0.2705 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0298 1.2948 0.1037 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7656 1.5959 -2.1514 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7002 2.3351 0.4351 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0672 -3.4866 0.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2922 -1.4657 1.7388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6171 -2.1004 2.2089 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5513 0.3823 1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0620 0.7219 1.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8865 0.7298 1.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2641 0.6616 2.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8248 -1.1477 -1.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4105 -1.1179 -2.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8017 -0.6994 -0.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4110 1.8978 -1.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7284 -0.1433 -1.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9098 -0.5442 -0.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5528 1.1261 0.9269 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8614 1.1802 -3.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 3.2152 -0.0523 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 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 10 13 1 0 13 14 2 0 5 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 15 20 1 0 17 3 1 0 12 7 1 0 1 21 1 0 2 22 1 0 2 23 1 0 3 24 1 1 5 25 1 1 8 26 1 0 9 27 1 0 11 28 1 0 12 29 1 0 13 30 1 0 15 31 1 6 16 32 1 6 17 33 1 6 18 34 1 0 19 35 1 0 20 36 1 0 M END

Standard InCHIKey	OLZAGZCCJJBKNZ-SYLRKERUSA-N
Standard InCHI	InChI=1S/C13H16O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-5,9-13,15-18H,6H2/t9-,10-,11-,12-,13-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2ccc(cc2)C=O)[C@@H]([C@@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	284.09	Volume:	267.277 ? Van der Waals volume.
Dense:	1.063	LogP:	-0.774 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.291 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.149 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	13.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.507	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.429	Fsp³:	0.462
MCE-18:	45.842 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.615	Fluc inhibitor:	0.041 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.094 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.017 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.406	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.966	MDCK Permeability:	-5.0
Pgp-inhibitor:	0.002	Pgp-substrate:	0.009
PAMPA:	0.983 ? 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):	0.753
20% Bioavailability (F20%):	0.484	30% Bioavailability (F30%):	0.964
50% Bioavailability (F50%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.0
Plasma Protein Binding (PPB):	57.032%	Volume Distribution (VD):	-0.386
Fu:	42.22% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.044
BSEP inhibitor:	0.469

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.089
HLM stability:	0.005 ? 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):

2.121

Half-life (T1/2):

3.401

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.211
Human Hepatotoxicity (H-HT):	0.461	Drug-induced Liver Injury (DILI):	0.338
AMES Toxicity:	0.738	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	0.962
Carcinogencity:	0.241	Eye Corrosion:	0.012
Eye Irritation:	0.74	Respiratory Toxicity:	0.029
Drug-induced Neurotoxicity:	0.038	Ototoxicity:	0.851
Hematotoxicity:	0.236	Drug-induced Nephrotoxicity:	0.335
Genotoxicity:	0.018	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.034	Hek293 Cytotoxicity:	0.081
BCF:	0.25 ? 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:	2.707 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.424 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.493 ? 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
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387653]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22325941]
NPO23779	Premna subscandens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24926	Fomes fomentarius	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24970	Anthurium versicolor	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24525	Desmanthodium perfoliatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25276	Ligusticum scoticum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23779	Premna subscandens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25276	Ligusticum scoticum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23662	Arthraxon hispidus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25276	Ligusticum scoticum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24852	Helicia nilagirica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23779	Premna subscandens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25139	Cocculus sarmentosus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23523	Triumfetta cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24926	Fomes fomentarius	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24729	Securinega tinctoria	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23323	Dianthus superbus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25276	Ligusticum scoticum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23662	Arthraxon hispidus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24970	Anthurium versicolor	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24685	Ramalina dilacerata	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24525	Desmanthodium perfoliatum	Species	Asteraceae	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	4
Inhibition	2

Activity Type	# Activity
Individual protein	5
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2668	Individual protein	Acetylcholinesterase	Torpedo californica	Inhibition	=	24.84	%	PMID[19726199]
NPT675	Individual protein	Succinate semialdehyde dehydrogenase	Homo sapiens	IC50	>	1000000.0	nM	PMID[16290145]
NPT674	Individual protein	Gamma-amino-N-butyrate transaminase	Homo sapiens	IC50	>	1000000.0	nM	PMID[16290145]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	IC50	=	2540000.0	nM	PMID[18996693]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	10.0	%	PMID[18996693]

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	>	20000.0	nM	PMID[28274626]

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 NPC212729 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	17060
0.1-0.2	28905
0.2-0.3	2763
0.3-0.4	715
0.4-0.5	292
0.5-0.6	80
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC604498
0.7857	Intermediate Similarity	NPC269242
0.7674	Intermediate Similarity	NPC294470
0.7333	Intermediate Similarity	NPC60589
0.7333	Intermediate Similarity	NPC469708
0.7333	Intermediate Similarity	NPC609376
0.7174	Intermediate Similarity	NPC200092
0.7021	Intermediate Similarity	NPC80098
0.6818	Remote Similarity	NPC142319
0.6809	Remote Similarity	NPC608788
0.68	Remote Similarity	NPC251102
0.68	Remote Similarity	NPC210298
0.6667	Remote Similarity	NPC228907
0.6471	Remote Similarity	NPC604356
0.6346	Remote Similarity	NPC26080
0.6346	Remote Similarity	NPC165686
0.6275	Remote Similarity	NPC218685
0.625	Remote Similarity	NPC604439
0.617	Remote Similarity	NPC153149
0.6154	Remote Similarity	NPC479028
0.6154	Remote Similarity	NPC479031
0.6122	Remote Similarity	NPC226712
0.6087	Remote Similarity	NPC276195
0.6042	Remote Similarity	NPC25817
0.5957	Remote Similarity	NPC217854
0.5882	Remote Similarity	NPC214454
0.5882	Remote Similarity	NPC166040
0.5833	Remote Similarity	NPC192810
0.58	Remote Similarity	NPC12308
0.5769	Remote Similarity	NPC310661
0.5769	Remote Similarity	NPC9912
0.5714	Remote Similarity	NPC9248
0.5686	Remote Similarity	NPC221090
0.5625	Remote Similarity	NPC484157
0.5614	Remote Similarity	NPC146540
0.56	Remote Similarity	NPC299144
0.5577	Remote Similarity	NPC166168
0.5556	Remote Similarity	NPC472024
0.5556	Remote Similarity	NPC270849
0.5556	Remote Similarity	NPC205054
0.5556	Remote Similarity	NPC23084
0.5556	Remote Similarity	NPC19470
0.5556	Remote Similarity	NPC606892
0.5536	Remote Similarity	NPC222455
0.5517	Remote Similarity	NPC294166
0.5517	Remote Similarity	NPC115022
0.55	Remote Similarity	NPC248119
0.55	Remote Similarity	NPC175275
0.5472	Remote Similarity	NPC40377
0.5455	Remote Similarity	NPC26653
0.5455	Remote Similarity	NPC214910
0.5455	Remote Similarity	NPC80600
0.5455	Remote Similarity	NPC164599
0.5455	Remote Similarity	NPC481303
0.5424	Remote Similarity	NPC479030
0.5424	Remote Similarity	NPC37468
0.5424	Remote Similarity	NPC186418
0.5424	Remote Similarity	NPC8497
0.541	Remote Similarity	NPC264381
0.541	Remote Similarity	NPC259767
0.541	Remote Similarity	NPC295970
0.54	Remote Similarity	NPC152722
0.5385	Remote Similarity	NPC69513
0.5385	Remote Similarity	NPC145900
0.5357	Remote Similarity	NPC248355
0.5357	Remote Similarity	NPC479029
0.5323	Remote Similarity	NPC471029
0.5323	Remote Similarity	NPC601944
0.5294	Remote Similarity	NPC198798
0.5283	Remote Similarity	NPC48863
0.5283	Remote Similarity	NPC251981
0.5283	Remote Similarity	NPC13745
0.5273	Remote Similarity	NPC485268
0.5273	Remote Similarity	NPC83975
0.5263	Remote Similarity	NPC55040
0.5246	Remote Similarity	NPC210192
0.5238	Remote Similarity	NPC186406
0.5192	Remote Similarity	NPC36434
0.5185	Remote Similarity	NPC215833
0.5179	Remote Similarity	NPC210015
0.5179	Remote Similarity	NPC210478
0.5172	Remote Similarity	NPC302378
0.5172	Remote Similarity	NPC59324
0.5172	Remote Similarity	NPC85799
0.5172	Remote Similarity	NPC303422
0.5172	Remote Similarity	NPC218003
0.5172	Remote Similarity	NPC232673
0.5172	Remote Similarity	NPC34456
0.5167	Remote Similarity	NPC479374
0.5161	Remote Similarity	NPC57587
0.5156	Remote Similarity	NPC185103
0.5156	Remote Similarity	NPC170475
0.5091	Remote Similarity	NPC49074
0.5088	Remote Similarity	NPC57751
0.5088	Remote Similarity	NPC105827
0.5088	Remote Similarity	NPC609351
0.5085	Remote Similarity	NPC100389
0.5085	Remote Similarity	NPC269421
0.5082	Remote Similarity	NPC474044
0.5082	Remote Similarity	NPC121001
0.5079	Remote Similarity	NPC605700
0.5079	Remote Similarity	NPC606353
0.5077	Remote Similarity	NPC169761
0.5077	Remote Similarity	NPC26195

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC212729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3848
0.1-0.2	5072
0.2-0.3	194
0.3-0.4	30
0.4-0.5	5
0.5-0.6	0
0.6-0.7	1
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
0.6122	Remote Similarity	NPD1091	Pre-clinical

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