NPASS Compound

Natural Product: NPC158674

Natural Product ID	NPC158674
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SCNKDAJBBGDFOB-FDNTWFBCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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 56 59 0 0 0 0 0 0 0 0999 V2000 -3.9943 2.8917 0.7799 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6802 1.4465 0.5704 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7659 0.7186 -0.1913 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4006 -0.7396 -0.1670 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9681 -1.0198 0.2166 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0003 0.0129 -0.1012 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 1.3118 -0.2001 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9866 0.1650 0.9137 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3126 0.4684 0.5534 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6423 1.8310 0.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2761 2.6519 0.5477 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8959 2.2001 0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2311 3.5138 -0.1888 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5338 3.8170 -0.5615 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4662 2.8335 -0.7374 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1320 1.5187 -0.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8399 1.2056 -0.1774 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5356 -0.0323 -0.0017 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2933 -0.4360 0.3626 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0947 -1.8703 0.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0423 -2.4242 1.1949 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0995 -3.8166 1.2597 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8329 -4.6254 0.6472 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9127 -4.0797 -0.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0344 -2.7164 -0.0879 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8634 -4.8882 -0.6578 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7243 -6.0075 0.6909 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1872 -4.3549 1.9465 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7595 3.1721 -1.1103 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7792 2.2322 -1.3129 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2693 4.4936 -0.0047 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6441 -2.1981 -0.5079 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7565 -1.3528 -1.3798 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0208 0.9308 0.3738 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0385 2.9578 1.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3390 3.3073 1.5679 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0034 3.4806 -0.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5092 0.9482 1.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7560 1.0323 -1.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0579 -1.2194 0.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9259 -1.3239 1.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -0.1213 -1.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8321 4.8477 -0.7196 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8522 0.7047 -0.6798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6846 -1.8200 1.7129 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8865 -2.2842 -0.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8368 -4.6932 -0.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4374 -6.6089 0.3508 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4593 -3.9518 2.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7020 2.8146 -1.5859 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9519 1.5718 -0.4516 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4834 1.6089 -2.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1301 4.8924 0.9204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5099 -1.9739 -1.4627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6522 -2.3194 -1.3430 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6034 1.2960 -0.3372 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 22 28 1 0 15 29 1 0 29 30 1 0 13 31 1 0 5 32 1 0 4 33 1 0 3 34 1 0 7 2 1 0 19 9 2 0 25 20 1 0 17 12 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 6 4 40 1 1 5 41 1 1 6 42 1 6 14 43 1 0 16 44 1 0 21 45 1 0 25 46 1 0 26 47 1 0 27 48 1 0 28 49 1 0 30 50 1 0 30 51 1 0 30 52 1 0 31 53 1 0 32 54 1 0 33 55 1 0 34 56 1 0 M END

Standard InCHIKey	SCNKDAJBBGDFOB-FDNTWFBCSA-N
Standard InCHI	InChI=1S/C22H22O12/c1-7-15(26)18(29)19(30)22(32-7)34-21-17(28)14-10(23)5-9(31-2)6-13(14)33-20(21)8-3-11(24)16(27)12(25)4-8/h3-7,15,18-19,22-27,29-30H,1-2H3/t7-,15-,18+,19+,22-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1cc(c(c(c1)O)O)O)OC)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	478.11	Volume:	439.233 ? Van der Waals volume.
Dense:	1.089	LogP:	1.16 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.473 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.988 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	199.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.257	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.094	Fsp³:	0.318
MCE-18:	93.655 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.634	Fluc inhibitor:	0.172 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.949 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.887 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.129	Promiscuous compounds:	0.836

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.044	MDCK Permeability:	-5.174
Pgp-inhibitor:	0.001	Pgp-substrate:	0.306
PAMPA:	0.99 ? 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):	0.208
20% Bioavailability (F20%):	0.448	30% Bioavailability (F30%):	0.857
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.185
Plasma Protein Binding (PPB):	85.283%	Volume Distribution (VD):	-0.027
Fu:	14.406% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.86
BSEP inhibitor:	0.139

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.091	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.812
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.261
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.978 ? 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):

3.615

Half-life (T1/2):

3.06

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.665
Human Hepatotoxicity (H-HT):	0.353	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.756	Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.299	Skin Sensitization:	0.999
Carcinogencity:	0.116	Eye Corrosion:	0.001
Eye Irritation:	0.863	Respiratory Toxicity:	0.089
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.932
Hematotoxicity:	0.024	Drug-induced Nephrotoxicity:	0.022
Genotoxicity:	0.922	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.918	Hek293 Cytotoxicity:	0.246
BCF:	0.665 ? 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:	3.362 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.692 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.963 ? 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
NPO17083	Atraphaxis frutescens	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28006914]
NPO17083	Atraphaxis frutescens	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17083	Atraphaxis frutescens	Species	Polygonaceae	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	3

Activity Type	# Activity
Others	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
NPT35	Others	n.a.	n.a.	IC50	=	23200.0	nM	PMID[28006914]
NPT2	Others	Unspecified	n.a.	IC50	>	300000.0	nM	PMID[28006914]
NPT2	Others	Unspecified	n.a.	IC50	=	1100000.0	nM	PMID[28006914]

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 NPC158674 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	21256
0.1-0.2	24976
0.2-0.3	2651
0.3-0.4	524
0.4-0.5	247
0.5-0.6	128
0.6-0.7	45
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8714	High Similarity	NPC271692
0.8194	Intermediate Similarity	NPC46420
0.7733	Intermediate Similarity	NPC611303
0.7703	Intermediate Similarity	NPC349108
0.7671	Intermediate Similarity	NPC249281
0.7534	Intermediate Similarity	NPC135599
0.7534	Intermediate Similarity	NPC73855
0.7534	Intermediate Similarity	NPC113968
0.7534	Intermediate Similarity	NPC328940
0.7534	Intermediate Similarity	NPC277174
0.7534	Intermediate Similarity	NPC606877
0.7532	Intermediate Similarity	NPC605784
0.7297	Intermediate Similarity	NPC473043
0.7215	Intermediate Similarity	NPC355481
0.7089	Intermediate Similarity	NPC116458
0.7089	Intermediate Similarity	NPC246943
0.7037	Intermediate Similarity	NPC480463
0.7013	Intermediate Similarity	NPC27640
0.7	Intermediate Similarity	NPC276377
0.6883	Remote Similarity	NPC136042
0.6829	Remote Similarity	NPC251417
0.6795	Remote Similarity	NPC84362
0.6786	Remote Similarity	NPC293626
0.6753	Remote Similarity	NPC238376
0.6709	Remote Similarity	NPC59534
0.6706	Remote Similarity	NPC186816
0.6667	Remote Similarity	NPC267680
0.6667	Remote Similarity	NPC265530
0.6667	Remote Similarity	NPC606657
0.6591	Remote Similarity	NPC486577
0.6588	Remote Similarity	NPC150164
0.6582	Remote Similarity	NPC305811
0.6538	Remote Similarity	NPC289667
0.6538	Remote Similarity	NPC127546
0.6538	Remote Similarity	NPC57625
0.6538	Remote Similarity	NPC19709
0.6538	Remote Similarity	NPC173637
0.6538	Remote Similarity	NPC317489
0.6538	Remote Similarity	NPC223424
0.6538	Remote Similarity	NPC600591
0.6471	Remote Similarity	NPC39834
0.6456	Remote Similarity	NPC297987
0.6329	Remote Similarity	NPC19388
0.6329	Remote Similarity	NPC240431
0.6329	Remote Similarity	NPC55786
0.631	Remote Similarity	NPC265115
0.6292	Remote Similarity	NPC72016
0.6279	Remote Similarity	NPC227508
0.622	Remote Similarity	NPC219904
0.6203	Remote Similarity	NPC111929
0.6203	Remote Similarity	NPC320283
0.6203	Remote Similarity	NPC41121
0.6163	Remote Similarity	NPC480466
0.6125	Remote Similarity	NPC108831
0.6125	Remote Similarity	NPC182634
0.6111	Remote Similarity	NPC32641
0.6111	Remote Similarity	NPC256188
0.6111	Remote Similarity	NPC35119
0.6071	Remote Similarity	NPC223747
0.6067	Remote Similarity	NPC240306
0.6	Remote Similarity	NPC470443
0.6	Remote Similarity	NPC483414
0.6	Remote Similarity	NPC331652
0.6	Remote Similarity	NPC483415
0.5957	Remote Similarity	NPC14187
0.5949	Remote Similarity	NPC34531
0.5934	Remote Similarity	NPC483416
0.5876	Remote Similarity	NPC480441
0.587	Remote Similarity	NPC142142
0.5833	Remote Similarity	NPC488071
0.573	Remote Similarity	NPC67105
0.5729	Remote Similarity	NPC121703
0.5714	Remote Similarity	NPC126784
0.5714	Remote Similarity	NPC241423
0.5667	Remote Similarity	NPC203259
0.5667	Remote Similarity	NPC33054
0.5667	Remote Similarity	NPC210073
0.5667	Remote Similarity	NPC176740
0.5667	Remote Similarity	NPC471725
0.5667	Remote Similarity	NPC134532
0.5667	Remote Similarity	NPC602582
0.5663	Remote Similarity	NPC277205
0.5663	Remote Similarity	NPC37919
0.5647	Remote Similarity	NPC182121
0.5634	Remote Similarity	NPC188871
0.5556	Remote Similarity	NPC25523
0.5556	Remote Similarity	NPC275454
0.5543	Remote Similarity	NPC64425
0.5529	Remote Similarity	NPC42773
0.5529	Remote Similarity	NPC472459
0.5529	Remote Similarity	NPC45522
0.5529	Remote Similarity	NPC599850
0.5506	Remote Similarity	NPC278419
0.5506	Remote Similarity	NPC179198
0.55	Remote Similarity	NPC277532
0.5495	Remote Similarity	NPC22062
0.5495	Remote Similarity	NPC473634
0.5495	Remote Similarity	NPC138811
0.5476	Remote Similarity	NPC145038
0.5476	Remote Similarity	NPC56077
0.5476	Remote Similarity	NPC281131
0.5476	Remote Similarity	NPC253662
0.5476	Remote Similarity	NPC179950
0.5476	Remote Similarity	NPC88789
0.5476	Remote Similarity	NPC189142
0.5476	Remote Similarity	NPC77660
0.5476	Remote Similarity	NPC491374
0.5474	Remote Similarity	NPC473073
0.5465	Remote Similarity	NPC175107
0.5426	Remote Similarity	NPC209296
0.5426	Remote Similarity	NPC473327
0.5422	Remote Similarity	NPC476771
0.5412	Remote Similarity	NPC24043
0.5405	Remote Similarity	NPC58382
0.5402	Remote Similarity	NPC486578
0.5393	Remote Similarity	NPC116864
0.5393	Remote Similarity	NPC244776
0.5385	Remote Similarity	NPC173582
0.5385	Remote Similarity	NPC265885
0.5385	Remote Similarity	NPC181465
0.5385	Remote Similarity	NPC215710
0.5385	Remote Similarity	NPC473438
0.5385	Remote Similarity	NPC253788
0.5368	Remote Similarity	NPC5319
0.5357	Remote Similarity	NPC476772
0.5349	Remote Similarity	NPC325555
0.5349	Remote Similarity	NPC226304
0.5326	Remote Similarity	NPC65563
0.5326	Remote Similarity	NPC470949
0.5326	Remote Similarity	NPC605592
0.5312	Remote Similarity	NPC476472
0.5312	Remote Similarity	NPC294815
0.5312	Remote Similarity	NPC16194
0.5294	Remote Similarity	NPC64305
0.5294	Remote Similarity	NPC95090
0.5294	Remote Similarity	NPC27408
0.5281	Remote Similarity	NPC190003
0.5278	Remote Similarity	NPC103904
0.5278	Remote Similarity	NPC262094
0.5275	Remote Similarity	NPC609888
0.5269	Remote Similarity	NPC473571
0.5269	Remote Similarity	NPC110941
0.5258	Remote Similarity	NPC470445
0.5238	Remote Similarity	NPC160515
0.5233	Remote Similarity	NPC181712
0.5227	Remote Similarity	NPC22832
0.5227	Remote Similarity	NPC120099
0.5217	Remote Similarity	NPC196127
0.5217	Remote Similarity	NPC44931
0.5208	Remote Similarity	NPC64755
0.5205	Remote Similarity	NPC76376
0.5205	Remote Similarity	NPC146679
0.5205	Remote Similarity	NPC605755
0.5176	Remote Similarity	NPC261866
0.5176	Remote Similarity	NPC77672
0.5176	Remote Similarity	NPC133671
0.5176	Remote Similarity	NPC135391
0.5176	Remote Similarity	NPC78263
0.5176	Remote Similarity	NPC250069
0.5176	Remote Similarity	NPC348541
0.5172	Remote Similarity	NPC138927
0.5169	Remote Similarity	NPC607707
0.514	Remote Similarity	NPC209550
0.514	Remote Similarity	NPC138990
0.5119	Remote Similarity	NPC67037
0.5119	Remote Similarity	NPC255615
0.5116	Remote Similarity	NPC323593
0.5116	Remote Similarity	NPC203500
0.5114	Remote Similarity	NPC285197
0.5111	Remote Similarity	NPC203050
0.5111	Remote Similarity	NPC488072
0.5111	Remote Similarity	NPC225434
0.5111	Remote Similarity	NPC66087
0.5111	Remote Similarity	NPC267254
0.5111	Remote Similarity	NPC601586
0.5109	Remote Similarity	NPC258044
0.5109	Remote Similarity	NPC217387
0.5104	Remote Similarity	NPC37668
0.5093	Remote Similarity	NPC175429
0.5067	Remote Similarity	NPC270620
0.5057	Remote Similarity	NPC52550
0.5057	Remote Similarity	NPC488080
0.5057	Remote Similarity	NPC169977
0.5057	Remote Similarity	NPC603655
0.5056	Remote Similarity	NPC243930
0.5056	Remote Similarity	NPC21666
0.5056	Remote Similarity	NPC189913
0.5055	Remote Similarity	NPC95866
0.5054	Remote Similarity	NPC67326
0.5053	Remote Similarity	NPC488073
0.5053	Remote Similarity	NPC153755
0.5053	Remote Similarity	NPC488074

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5252
0.1-0.2	3843
0.2-0.3	46
0.3-0.4	3
0.4-0.5	1
0.5-0.6	4
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
0.6517	Remote Similarity	NPD7251	Phase 2
0.5895	Remote Similarity	NPD7808	Phase 3
0.5667	Remote Similarity	NPD6797	Phase 2
0.5426	Remote Similarity	NPD7054	Phase 4
0.5368	Remote Similarity	NPD7804	Clinical (unspecified phase)

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