NPASS Compound

Natural Product: NPC172270

Natural Product ID	NPC172270
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WPLPEWXTXFTSCF-ZTHZTRLZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102206557
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 60 63 0 0 0 0 0 0 0 0999 V2000 -3.0802 -6.8651 1.3598 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6476 -5.4990 1.0106 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9269 -5.3207 -0.0047 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9863 -4.3615 1.7402 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5634 -3.0951 1.3842 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3047 -2.3040 0.5437 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8270 -1.0436 0.2233 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6406 -0.5511 0.7122 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9171 -1.3514 1.5480 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3736 -2.6321 1.8904 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2620 0.8218 0.3730 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0237 1.3660 0.4920 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2329 2.6969 0.1466 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3483 3.2455 0.2407 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8256 3.4320 -0.3249 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6395 4.7311 -0.6787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6626 5.5128 -1.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9106 4.9433 -1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1194 3.6417 -0.9271 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0772 2.8628 -0.4442 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2194 1.6302 -0.0997 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9477 5.7001 -1.7515 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7534 7.0477 -2.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6061 5.2952 -0.5592 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0614 0.6484 0.9428 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9993 0.0297 0.0922 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4056 0.5576 0.2294 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1127 -0.3506 1.2454 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2189 -1.7209 0.6130 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0296 -2.0055 -0.2744 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6615 -3.4940 -0.2290 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6729 -4.2810 -0.7365 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9461 -1.3320 0.2563 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3787 -1.8699 -0.1433 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3877 -0.4638 2.4118 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1003 0.3715 -0.9803 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3855 -7.4601 0.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8485 -6.8989 2.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1851 -7.3922 1.7762 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 -2.7000 0.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -0.4455 -0.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0062 -1.0504 2.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7910 -3.2590 2.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5293 6.5426 -1.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0787 3.1407 -0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7192 7.5399 -2.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1252 7.0478 -3.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2594 7.6144 -1.3148 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8997 5.8843 0.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6559 0.2463 -0.9614 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4990 1.6036 0.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1618 0.0084 1.4072 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2296 -2.5160 1.3873 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2145 -1.7725 -1.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7072 -3.5778 -0.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4211 -3.7382 0.8413 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4360 -4.2256 -0.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2307 -1.8373 -1.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1120 0.4443 2.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5678 0.8078 -1.6900 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 8 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 18 22 1 0 22 23 1 0 16 24 1 0 12 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 29 34 1 0 28 35 1 0 27 36 1 0 10 5 1 0 21 11 1 0 33 26 1 0 20 15 1 0 1 37 1 0 1 38 1 0 1 39 1 0 6 40 1 0 7 41 1 0 9 42 1 0 10 43 1 0 17 44 1 0 19 45 1 0 23 46 1 0 23 47 1 0 23 48 1 0 24 49 1 0 26 50 1 6 27 51 1 1 28 52 1 1 29 53 1 1 30 54 1 6 31 55 1 0 31 56 1 0 32 57 1 0 34 58 1 0 35 59 1 0 36 60 1 0 M END

Standard InCHIKey	WPLPEWXTXFTSCF-ZTHZTRLZSA-N
Standard InCHI	InChI=1S/C24H24O12/c1-10(26)33-12-5-3-11(4-6-12)22-23(36-24-21(31)20(30)18(28)16(9-25)35-24)19(29)17-14(27)7-13(32-2)8-15(17)34-22/h3-8,16,18,20-21,24-25,27-28,30-31H,9H2,1-2H3/t16-,18-,20+,21-,24+/m1/s1
SMILES	CC(=O)Oc1ccc(cc1)c1c(c(=O)c2c(cc(cc2o1)OC)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.13	Volume:	471.189 ? Van der Waals volume.
Dense:	1.07	LogP:	1.384 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.74 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.258 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	185.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.228	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.883	Fsp³:	0.333
MCE-18:	89.438 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.568	Fluc inhibitor:	0.345 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.934 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.907 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.272

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.992	MDCK Permeability:	-5.029
Pgp-inhibitor:	0.006	Pgp-substrate:	0.122
PAMPA:	0.839 ? 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):	0.463
20% Bioavailability (F20%):	0.005	30% Bioavailability (F30%):	0.8
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.03
Plasma Protein Binding (PPB):	77.059%	Volume Distribution (VD):	-0.01
Fu:	23.104% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.353
BSEP inhibitor:	0.624

ADMET: Metabolism

CYP1A2-inhibitor:	0.182	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.989
HLM stability:	0.998 ? 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):

2.24

Half-life (T1/2):

2.522

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.083
Human Hepatotoxicity (H-HT):	0.607	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.829	Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.06	Skin Sensitization:	0.995
Carcinogencity:	0.248	Eye Corrosion:	0.0
Eye Irritation:	0.427	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.704
Hematotoxicity:	0.288	Drug-induced Nephrotoxicity:	0.266
Genotoxicity:	0.855	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.256	Hek293 Cytotoxicity:	0.225
BCF:	0.463 ? 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:	3.207 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.609 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.847 ? 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
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524113]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8173	Lupinus multiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2383	Mimosa acacioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5425	Polygala nyikensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10340	Crepis rubra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8173	Lupinus multiflorus	Species	Fabaceae	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

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 NPC172270 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	16018
0.1-0.2	29177
0.2-0.3	3293
0.3-0.4	808
0.4-0.5	324
0.5-0.6	122
0.6-0.7	65
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8493	Intermediate Similarity	NPC289667
0.7662	Intermediate Similarity	NPC297987
0.7436	Intermediate Similarity	NPC136042
0.7407	Intermediate Similarity	NPC116458
0.7407	Intermediate Similarity	NPC246943
0.7349	Intermediate Similarity	NPC251417
0.7342	Intermediate Similarity	NPC84362
0.725	Intermediate Similarity	NPC472459
0.7195	Intermediate Similarity	NPC605784
0.7128	Intermediate Similarity	NPC277532
0.7126	Intermediate Similarity	NPC64425
0.7125	Intermediate Similarity	NPC46420
0.7	Intermediate Similarity	NPC64305
0.6951	Remote Similarity	NPC611303
0.6914	Remote Similarity	NPC271692
0.679	Remote Similarity	NPC95090
0.679	Remote Similarity	NPC27408
0.679	Remote Similarity	NPC158674
0.6667	Remote Similarity	NPC249281
0.6667	Remote Similarity	NPC486578
0.6506	Remote Similarity	NPC24043
0.6471	Remote Similarity	NPC22832
0.6471	Remote Similarity	NPC120099
0.6413	Remote Similarity	NPC35119
0.64	Remote Similarity	NPC295625
0.6395	Remote Similarity	NPC607707
0.6374	Remote Similarity	NPC240306
0.6364	Remote Similarity	NPC470716
0.6353	Remote Similarity	NPC285197
0.6353	Remote Similarity	NPC488071
0.6327	Remote Similarity	NPC470715
0.6327	Remote Similarity	NPC25523
0.6322	Remote Similarity	NPC276377
0.6301	Remote Similarity	NPC153758
0.6279	Remote Similarity	NPC243930
0.6279	Remote Similarity	NPC21666
0.6265	Remote Similarity	NPC77672
0.6265	Remote Similarity	NPC133671
0.6265	Remote Similarity	NPC135391
0.6265	Remote Similarity	NPC78263
0.6265	Remote Similarity	NPC250069
0.625	Remote Similarity	NPC14187
0.6237	Remote Similarity	NPC32641
0.6237	Remote Similarity	NPC256188
0.6237	Remote Similarity	NPC606657
0.6214	Remote Similarity	NPC470720
0.619	Remote Similarity	NPC277205
0.619	Remote Similarity	NPC37919
0.6186	Remote Similarity	NPC121703
0.617	Remote Similarity	NPC5319
0.6163	Remote Similarity	NPC60735
0.6163	Remote Similarity	NPC26230
0.6162	Remote Similarity	NPC480441
0.6162	Remote Similarity	NPC164704
0.6154	Remote Similarity	NPC150164
0.6118	Remote Similarity	NPC488080
0.6118	Remote Similarity	NPC169977
0.6118	Remote Similarity	NPC73511
0.6117	Remote Similarity	NPC470717
0.6092	Remote Similarity	NPC148710
0.6092	Remote Similarity	NPC609478
0.6087	Remote Similarity	NPC186816
0.6047	Remote Similarity	NPC42773
0.6047	Remote Similarity	NPC45522
0.6047	Remote Similarity	NPC325555
0.6047	Remote Similarity	NPC226304
0.6047	Remote Similarity	NPC599850
0.6	Remote Similarity	NPC145038
0.6	Remote Similarity	NPC56077
0.6	Remote Similarity	NPC281131
0.6	Remote Similarity	NPC253662
0.6	Remote Similarity	NPC179950
0.6	Remote Similarity	NPC323593
0.6	Remote Similarity	NPC88789
0.6	Remote Similarity	NPC203500
0.6	Remote Similarity	NPC189142
0.6	Remote Similarity	NPC77660
0.6	Remote Similarity	NPC491374
0.5962	Remote Similarity	NPC470719
0.5955	Remote Similarity	NPC203050
0.5955	Remote Similarity	NPC488072
0.5955	Remote Similarity	NPC225434
0.5955	Remote Similarity	NPC601586
0.5934	Remote Similarity	NPC480466
0.5895	Remote Similarity	NPC72016
0.589	Remote Similarity	NPC262094
0.5882	Remote Similarity	NPC19388
0.5882	Remote Similarity	NPC58053
0.5882	Remote Similarity	NPC261866
0.5882	Remote Similarity	NPC240431
0.5882	Remote Similarity	NPC39360
0.5882	Remote Similarity	NPC55786
0.5882	Remote Similarity	NPC29763
0.5882	Remote Similarity	NPC210003
0.5843	Remote Similarity	NPC311830
0.5833	Remote Similarity	NPC486577
0.5824	Remote Similarity	NPC480463
0.5816	Remote Similarity	NPC135358
0.5773	Remote Similarity	NPC76831
0.5747	Remote Similarity	NPC186807
0.5747	Remote Similarity	NPC181712
0.5747	Remote Similarity	NPC603655
0.573	Remote Similarity	NPC101026
0.573	Remote Similarity	NPC488077
0.5714	Remote Similarity	NPC265115
0.567	Remote Similarity	NPC142142
0.5632	Remote Similarity	NPC8573
0.5632	Remote Similarity	NPC234739
0.5618	Remote Similarity	NPC307938
0.5618	Remote Similarity	NPC219904
0.5604	Remote Similarity	NPC355481
0.5568	Remote Similarity	NPC22195
0.5568	Remote Similarity	NPC27640
0.5568	Remote Similarity	NPC21190
0.5556	Remote Similarity	NPC601144
0.5529	Remote Similarity	NPC288084
0.5521	Remote Similarity	NPC488073
0.5474	Remote Similarity	NPC22062
0.5474	Remote Similarity	NPC473634
0.5474	Remote Similarity	NPC138811
0.5474	Remote Similarity	NPC156869
0.5444	Remote Similarity	NPC168584
0.5426	Remote Similarity	NPC139320
0.5421	Remote Similarity	NPC470713
0.5417	Remote Similarity	NPC131745
0.5413	Remote Similarity	NPC138990
0.5402	Remote Similarity	NPC111929
0.5402	Remote Similarity	NPC320283
0.5402	Remote Similarity	NPC41121
0.5385	Remote Similarity	NPC470712
0.5385	Remote Similarity	NPC80188
0.5385	Remote Similarity	NPC605067
0.5368	Remote Similarity	NPC275454
0.5364	Remote Similarity	NPC175429
0.5361	Remote Similarity	NPC46202
0.5357	Remote Similarity	NPC134819
0.5341	Remote Similarity	NPC44558
0.5341	Remote Similarity	NPC238376
0.5341	Remote Similarity	NPC143851
0.5333	Remote Similarity	NPC59534
0.5333	Remote Similarity	NPC117260
0.5326	Remote Similarity	NPC206123
0.5326	Remote Similarity	NPC220169
0.5319	Remote Similarity	NPC473682
0.5319	Remote Similarity	NPC278419
0.5319	Remote Similarity	NPC179198
0.5306	Remote Similarity	NPC483414
0.5304	Remote Similarity	NPC223860
0.53	Remote Similarity	NPC475382
0.5288	Remote Similarity	NPC48984
0.5287	Remote Similarity	NPC67037
0.5287	Remote Similarity	NPC255615
0.5281	Remote Similarity	NPC197896
0.5281	Remote Similarity	NPC313163
0.5281	Remote Similarity	NPC265530
0.5275	Remote Similarity	NPC175107
0.5275	Remote Similarity	NPC609451
0.5273	Remote Similarity	NPC209550
0.5269	Remote Similarity	NPC267254
0.5263	Remote Similarity	NPC103904
0.5263	Remote Similarity	NPC609888
0.5256	Remote Similarity	NPC270620
0.5253	Remote Similarity	NPC473623
0.5253	Remote Similarity	NPC209296
0.5253	Remote Similarity	NPC473327
0.5238	Remote Similarity	NPC191154
0.5222	Remote Similarity	NPC305811
0.5222	Remote Similarity	NPC45638
0.5222	Remote Similarity	NPC349108
0.5213	Remote Similarity	NPC116864
0.5213	Remote Similarity	NPC244776
0.5208	Remote Similarity	NPC267680
0.5208	Remote Similarity	NPC471748
0.5204	Remote Similarity	NPC153755
0.52	Remote Similarity	NPC488089
0.5195	Remote Similarity	NPC146679
0.5192	Remote Similarity	NPC189564
0.519	Remote Similarity	NPC236769
0.5182	Remote Similarity	NPC488078
0.5172	Remote Similarity	NPC34531
0.5169	Remote Similarity	NPC127546
0.5169	Remote Similarity	NPC57625
0.5169	Remote Similarity	NPC108831
0.5169	Remote Similarity	NPC19709
0.5169	Remote Similarity	NPC173637
0.5169	Remote Similarity	NPC317489
0.5169	Remote Similarity	NPC223424
0.5169	Remote Similarity	NPC182634
0.5169	Remote Similarity	NPC600591
0.5165	Remote Similarity	NPC21100
0.5165	Remote Similarity	NPC27942
0.5165	Remote Similarity	NPC60966
0.5165	Remote Similarity	NPC201292
0.5161	Remote Similarity	NPC223747
0.5155	Remote Similarity	NPC293626
0.5152	Remote Similarity	NPC470443
0.5152	Remote Similarity	NPC483415
0.5111	Remote Similarity	NPC93337
0.5111	Remote Similarity	NPC168822
0.5109	Remote Similarity	NPC479402

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC172270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4644
0.1-0.2	4389
0.2-0.3	101
0.3-0.4	8
0.4-0.5	4
0.5-0.6	3
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
0.617	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7808	Phase 3
0.5773	Remote Similarity	NPD7251	Phase 2
0.5253	Remote Similarity	NPD7054	Phase 4

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