NPASS Compound

Natural Product: NPC69938

Natural Product ID	NPC69938
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PZZRDJXEMZMZFD-ZMQFRBSTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5481217
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 49 52 0 0 0 0 0 0 0 0999 V2000 -2.5343 2.2613 0.6421 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6002 3.6086 0.8237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6356 4.4277 0.2834 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6280 3.8558 -0.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5693 2.4649 -0.6110 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5152 1.6290 -0.0830 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5707 0.1823 -0.2679 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 -0.5586 -0.7068 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6705 -1.9468 -0.8581 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2429 -2.6973 -1.2577 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8726 -2.5417 -0.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0531 -3.9235 -0.7005 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2661 -4.4971 -0.3948 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2913 -3.7060 0.0463 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1035 -2.3507 0.1803 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8897 -1.7366 -0.1200 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7056 -0.4569 0.0040 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5214 -4.3178 0.3521 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9912 -4.6955 -1.1506 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7438 -0.0515 -1.0199 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7916 -0.0544 -0.0522 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9046 -1.0000 -0.4733 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2638 -0.4300 -0.1570 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3220 0.4462 1.0408 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0433 1.1395 1.3673 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2538 1.1955 0.2300 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8032 -0.2460 2.1734 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7899 0.1915 -1.3018 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8934 -1.2393 -1.8507 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3482 4.6767 -0.9765 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7147 5.7939 0.4763 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2953 1.6328 1.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4136 4.0344 1.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2268 2.0959 -1.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4167 -5.5594 -0.4987 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8978 -1.7182 0.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3494 -3.7333 0.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3209 -5.0781 -0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3592 -0.4833 0.8791 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8114 -1.9828 0.0272 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9588 -1.2998 0.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0852 1.2485 0.8073 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2679 2.1459 1.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4848 0.5268 2.1083 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2894 0.4331 2.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5636 1.1307 -1.3647 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1983 -0.4612 -2.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0237 5.4263 -1.5904 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3254 6.2189 1.1468 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 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 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 4 30 1 0 3 31 1 0 6 1 1 0 17 7 1 0 26 21 1 0 16 11 1 0 1 32 1 0 2 33 1 0 5 34 1 0 13 35 1 0 15 36 1 0 18 37 1 0 19 38 1 0 21 39 1 1 22 40 1 1 23 41 1 1 24 42 1 6 25 43 1 0 25 44 1 0 27 45 1 0 28 46 1 0 29 47 1 0 30 48 1 0 31 49 1 0 M END

Standard InCHIKey	PZZRDJXEMZMZFD-ZMQFRBSTSA-N
Standard InCHI	InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15+,17+,20+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@H]([C@H]([C@@H](CO1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	434.08	Volume:	395.851 ? Van der Waals volume.
Dense:	1.097	LogP:	1.094 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.287 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.182 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	190.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.277	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.931	Fsp³:	0.25
MCE-18:	88.4 ? 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:	0.637	Fluc inhibitor:	0.308 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.946 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.676 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.105	Promiscuous compounds:	0.896

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.046	MDCK Permeability:	-4.984
Pgp-inhibitor:	0.0	Pgp-substrate:	0.732
PAMPA:	0.987 ? 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):	0.037
20% Bioavailability (F20%):	0.848	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.467
Plasma Protein Binding (PPB):	85.599%	Volume Distribution (VD):	-0.086
Fu:	13.412% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.923
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.905
BSEP inhibitor:	0.027

ADMET: Metabolism

CYP1A2-inhibitor:	0.01	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.01	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.792
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.066
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.952 ? 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):

3.66

Half-life (T1/2):

2.739

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.188
Human Hepatotoxicity (H-HT):	0.527	Drug-induced Liver Injury (DILI):	0.896
AMES Toxicity:	0.873	Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.492	Skin Sensitization:	1.0
Carcinogencity:	0.269	Eye Corrosion:	0.005
Eye Irritation:	0.98	Respiratory Toxicity:	0.202
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.655
Hematotoxicity:	0.096	Drug-induced Nephrotoxicity:	0.137
Genotoxicity:	0.96	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.92	Hek293 Cytotoxicity:	0.649
BCF:	0.695 ? 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:	3.329 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.556 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.975 ? 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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34332066]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	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 NPC69938 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	20591
0.1-0.2	26297
0.2-0.3	2032
0.3-0.4	509
0.4-0.5	213
0.5-0.6	102
0.6-0.7	68
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC276222
1.0	High Similarity	NPC274618
1.0	High Similarity	NPC118284
1.0	High Similarity	NPC608147
0.8906	High Similarity	NPC54802
0.8906	High Similarity	NPC197304
0.7895	Intermediate Similarity	NPC67326
0.7606	Intermediate Similarity	NPC127546
0.7606	Intermediate Similarity	NPC57625
0.7606	Intermediate Similarity	NPC173637
0.7606	Intermediate Similarity	NPC317489
0.7606	Intermediate Similarity	NPC223424
0.7606	Intermediate Similarity	NPC600591
0.75	Intermediate Similarity	NPC145038
0.75	Intermediate Similarity	NPC56077
0.75	Intermediate Similarity	NPC281131
0.75	Intermediate Similarity	NPC253662
0.75	Intermediate Similarity	NPC179950
0.75	Intermediate Similarity	NPC88789
0.75	Intermediate Similarity	NPC491374
0.7432	Intermediate Similarity	NPC175107
0.7324	Intermediate Similarity	NPC67037
0.7324	Intermediate Similarity	NPC255615
0.7273	Intermediate Similarity	NPC116864
0.7273	Intermediate Similarity	NPC244776
0.72	Intermediate Similarity	NPC235260
0.72	Intermediate Similarity	NPC155763
0.7089	Intermediate Similarity	NPC471079
0.7037	Intermediate Similarity	NPC255157
0.7037	Intermediate Similarity	NPC259896
0.6914	Remote Similarity	NPC203259
0.6914	Remote Similarity	NPC33054
0.6914	Remote Similarity	NPC176740
0.6914	Remote Similarity	NPC471725
0.6914	Remote Similarity	NPC134532
0.6914	Remote Similarity	NPC156869
0.6914	Remote Similarity	NPC602582
0.6757	Remote Similarity	NPC111929
0.6757	Remote Similarity	NPC320283
0.6757	Remote Similarity	NPC41121
0.6719	Remote Similarity	NPC286342
0.6711	Remote Similarity	NPC52550
0.6667	Remote Similarity	NPC77672
0.6667	Remote Similarity	NPC133671
0.6667	Remote Similarity	NPC135391
0.6667	Remote Similarity	NPC78263
0.6667	Remote Similarity	NPC250069
0.6533	Remote Similarity	NPC135599
0.6533	Remote Similarity	NPC73855
0.6533	Remote Similarity	NPC113968
0.6533	Remote Similarity	NPC328940
0.6533	Remote Similarity	NPC277174
0.6533	Remote Similarity	NPC606877
0.6486	Remote Similarity	NPC288084
0.6463	Remote Similarity	NPC29958
0.6447	Remote Similarity	NPC19388
0.6447	Remote Similarity	NPC240431
0.6447	Remote Similarity	NPC55786
0.6395	Remote Similarity	NPC37668
0.6386	Remote Similarity	NPC471748
0.6353	Remote Similarity	NPC488074
0.631	Remote Similarity	NPC304741
0.631	Remote Similarity	NPC605592
0.6292	Remote Similarity	NPC223426
0.6279	Remote Similarity	NPC245452
0.6267	Remote Similarity	NPC34531
0.625	Remote Similarity	NPC471669
0.6235	Remote Similarity	NPC144097
0.6222	Remote Similarity	NPC81042
0.622	Remote Similarity	NPC254855
0.622	Remote Similarity	NPC94610
0.622	Remote Similarity	NPC95866
0.6203	Remote Similarity	NPC138927
0.6197	Remote Similarity	NPC262699
0.6197	Remote Similarity	NPC131217
0.619	Remote Similarity	NPC173582
0.619	Remote Similarity	NPC265885
0.619	Remote Similarity	NPC181465
0.619	Remote Similarity	NPC215710
0.619	Remote Similarity	NPC473438
0.619	Remote Similarity	NPC253788
0.6173	Remote Similarity	NPC223747
0.6163	Remote Similarity	NPC154741
0.6154	Remote Similarity	NPC64305
0.6125	Remote Similarity	NPC159579
0.6125	Remote Similarity	NPC60735
0.6125	Remote Similarity	NPC219904
0.6125	Remote Similarity	NPC26230
0.6098	Remote Similarity	NPC203050
0.6098	Remote Similarity	NPC225434
0.6098	Remote Similarity	NPC276377
0.6049	Remote Similarity	NPC120099
0.6023	Remote Similarity	NPC122467
0.6022	Remote Similarity	NPC292019
0.6022	Remote Similarity	NPC202908
0.6	Remote Similarity	NPC472459
0.6	Remote Similarity	NPC470405
0.6	Remote Similarity	NPC39834
0.5977	Remote Similarity	NPC153755
0.5949	Remote Similarity	NPC265530
0.593	Remote Similarity	NPC155877
0.5926	Remote Similarity	NPC182121
0.5926	Remote Similarity	NPC129217
0.5897	Remote Similarity	NPC476771
0.5889	Remote Similarity	NPC135831
0.5889	Remote Similarity	NPC76831
0.5889	Remote Similarity	NPC89127
0.5875	Remote Similarity	NPC305811
0.5862	Remote Similarity	NPC129264
0.5854	Remote Similarity	NPC85707
0.5851	Remote Similarity	NPC219043
0.5843	Remote Similarity	NPC270448
0.5824	Remote Similarity	NPC292929
0.5824	Remote Similarity	NPC221342
0.5824	Remote Similarity	NPC476470
0.5823	Remote Similarity	NPC476772
0.5821	Remote Similarity	NPC103342
0.5802	Remote Similarity	NPC42773
0.5802	Remote Similarity	NPC45522
0.5802	Remote Similarity	NPC325555
0.5802	Remote Similarity	NPC226304
0.5795	Remote Similarity	NPC470125
0.575	Remote Similarity	NPC136042
0.5714	Remote Similarity	NPC476472
0.5714	Remote Similarity	NPC294815
0.5714	Remote Similarity	NPC85751
0.5714	Remote Similarity	NPC16194
0.5714	Remote Similarity	NPC19240
0.5699	Remote Similarity	NPC214621
0.5699	Remote Similarity	NPC34267
0.5698	Remote Similarity	NPC139320
0.5698	Remote Similarity	NPC609888
0.5679	Remote Similarity	NPC271692
0.5667	Remote Similarity	NPC473327
0.5663	Remote Similarity	NPC259957
0.5663	Remote Similarity	NPC189913
0.5663	Remote Similarity	NPC609478
0.5625	Remote Similarity	NPC303694
0.5618	Remote Similarity	NPC296018
0.561	Remote Similarity	NPC216496
0.561	Remote Similarity	NPC599850
0.5568	Remote Similarity	NPC473862
0.5542	Remote Similarity	NPC48093
0.5529	Remote Similarity	NPC170052
0.5529	Remote Similarity	NPC476215
0.5529	Remote Similarity	NPC135846
0.5521	Remote Similarity	NPC48984
0.5506	Remote Similarity	NPC35167
0.5488	Remote Similarity	NPC27640
0.5476	Remote Similarity	NPC484158
0.5476	Remote Similarity	NPC224530
0.5446	Remote Similarity	NPC156785
0.5444	Remote Similarity	NPC253521
0.5444	Remote Similarity	NPC488073
0.5444	Remote Similarity	NPC126784
0.5444	Remote Similarity	NPC241423
0.5444	Remote Similarity	NPC113836
0.5435	Remote Similarity	NPC97119
0.5432	Remote Similarity	NPC104677
0.5422	Remote Similarity	NPC59534
0.5417	Remote Similarity	NPC279989
0.5417	Remote Similarity	NPC189564
0.5412	Remote Similarity	NPC209023
0.5412	Remote Similarity	NPC605784
0.5385	Remote Similarity	NPC12013
0.5385	Remote Similarity	NPC11432
0.5385	Remote Similarity	NPC477613
0.5362	Remote Similarity	NPC184536
0.5357	Remote Similarity	NPC488071
0.5354	Remote Similarity	NPC139571
0.5352	Remote Similarity	NPC82325
0.534	Remote Similarity	NPC241781
0.5327	Remote Similarity	NPC275977
0.5326	Remote Similarity	NPC104883
0.5326	Remote Similarity	NPC488679
0.5312	Remote Similarity	NPC203145
0.5306	Remote Similarity	NPC217520
0.5301	Remote Similarity	NPC84362
0.5288	Remote Similarity	NPC192539
0.5286	Remote Similarity	NPC59951
0.5281	Remote Similarity	NPC163242
0.5281	Remote Similarity	NPC272068
0.5258	Remote Similarity	NPC488075
0.5244	Remote Similarity	NPC249281
0.5243	Remote Similarity	NPC480444
0.5204	Remote Similarity	NPC477895
0.5181	Remote Similarity	NPC297987
0.5158	Remote Similarity	NPC470445
0.5147	Remote Similarity	NPC179271
0.5146	Remote Similarity	NPC162394
0.5146	Remote Similarity	NPC488740
0.5146	Remote Similarity	NPC488736
0.5146	Remote Similarity	NPC488733
0.5143	Remote Similarity	NPC123886
0.5119	Remote Similarity	NPC46420
0.5119	Remote Similarity	NPC488080
0.5119	Remote Similarity	NPC169977
0.5114	Remote Similarity	NPC265115
0.5111	Remote Similarity	NPC196127
0.5106	Remote Similarity	NPC205824

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC69938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5192
0.1-0.2	3900
0.2-0.3	46
0.3-0.4	7
0.4-0.5	2
0.5-0.6	1
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
0.6914	Remote Similarity	NPD6797	Phase 2
0.5213	Remote Similarity	NPD7251	Phase 2

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