NPASS Compound

Natural Product: NPC290771

Natural Product ID	NPC290771
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WDQNUWOVEJHDOP-FOBVWLSUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102145128
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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 72 76 0 0 0 0 0 0 0 0999 V2000 -6.7677 0.6929 3.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3644 0.3507 2.0029 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5211 0.5370 1.0752 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0371 0.3961 -0.3517 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8934 1.4145 -0.4878 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7977 0.8489 0.3827 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7634 -0.5309 0.1815 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5258 -1.0630 -0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7532 -0.5913 -1.2017 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3795 -1.0141 -2.5152 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2186 -1.2516 -3.4917 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0863 -0.3145 -3.2216 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5327 -0.4737 -1.7939 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6382 -1.1834 -1.7889 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8917 -0.9922 -1.3272 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8405 -2.0225 -1.5346 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1187 -1.8922 -1.0950 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5178 -0.7541 -0.4378 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6082 0.2731 -0.2200 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2978 0.1432 -0.6689 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3997 1.2007 -0.4331 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8982 -0.6163 0.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8761 -1.5551 -0.1343 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1810 -1.3945 0.3217 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0555 -2.2766 0.1544 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4927 -0.2270 0.9706 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7797 0.0150 1.4611 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0202 1.2043 2.1000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0264 2.1438 2.2601 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7685 1.8883 1.7718 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4674 0.6919 1.1117 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2560 0.4978 0.6668 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2903 3.3537 2.9156 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7373 -0.9593 1.2737 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5087 -1.2743 -1.1419 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4827 1.0015 -3.3998 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8107 -2.5730 -3.4891 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1037 0.0362 -3.0685 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2449 1.1037 1.7046 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4107 2.5764 0.1435 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0296 0.6084 -1.2825 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4896 -0.4106 1.3952 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5255 -0.1228 4.1394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2318 1.5945 3.7901 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8479 0.9328 3.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0766 -0.7379 1.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9356 1.5739 1.1554 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5944 -0.6293 -0.4233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6244 1.6348 -1.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8314 1.3448 0.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8988 -1.0404 0.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6768 -2.1748 -0.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5338 0.4693 -1.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0209 -1.8970 -2.4371 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5729 -1.0182 -4.5326 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2784 -0.5382 -3.9331 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5154 0.5066 -1.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5165 -2.9134 -2.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8041 -2.7267 -1.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9337 1.1600 0.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5215 1.8231 0.3550 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6471 -2.4777 -0.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0206 1.4225 2.4959 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9600 2.6055 1.8803 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2072 3.7759 2.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0739 -1.4877 2.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 1.5796 -3.0300 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0380 -2.7342 -2.8973 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8176 0.3056 -3.9571 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8365 2.8341 0.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7398 0.1945 -2.1324 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7587 -0.8673 0.5616 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 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 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 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 29 33 1 0 27 34 1 0 13 35 1 0 12 36 1 0 11 37 1 0 10 38 1 0 6 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 39 2 1 0 35 9 1 0 20 15 1 0 32 22 1 0 31 26 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 3 47 1 6 4 48 1 1 5 49 1 6 6 50 1 6 8 51 1 0 8 52 1 0 9 53 1 6 10 54 1 1 11 55 1 6 12 56 1 6 13 57 1 1 16 58 1 0 17 59 1 0 19 60 1 0 21 61 1 0 23 62 1 0 28 63 1 0 30 64 1 0 33 65 1 0 34 66 1 0 36 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	WDQNUWOVEJHDOP-FOBVWLSUSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)41-15-3-2-10(4-12(15)29)16-7-14(31)19-13(30)5-11(28)6-17(19)40-16/h2-7,9,18,20-30,32-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3ccc(cc3O)c3cc(=O)c4c(cc(cc4o3)O)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	1.086 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.507 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.479 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.722	Fsp³:	0.444
MCE-18:	119.436 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.63	Fluc inhibitor:	0.313 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.939 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.704 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.15	Promiscuous compounds:	0.485

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.49	MDCK Permeability:	-5.115
Pgp-inhibitor:	0.0	Pgp-substrate:	0.97
PAMPA:	0.999 ? 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):	0.864
20% Bioavailability (F20%):	0.865	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.079
Plasma Protein Binding (PPB):	85.376%	Volume Distribution (VD):	-0.036
Fu:	13.014% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.984
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.634
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.013	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.018	CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.334
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.08 ? 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):

1.266

Half-life (T1/2):

4.475

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.225
Human Hepatotoxicity (H-HT):	0.386	Drug-induced Liver Injury (DILI):	0.947
AMES Toxicity:	0.838	Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.157	Skin Sensitization:	0.951
Carcinogencity:	0.1	Eye Corrosion:	0.0
Eye Irritation:	0.887	Respiratory Toxicity:	0.035
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.717
Hematotoxicity:	0.035	Drug-induced Nephrotoxicity:	0.383
Genotoxicity:	0.888	RPMI-8226 Immunitoxicity:	0.235
A549 Cytotoxicity:	0.458	Hek293 Cytotoxicity:	0.57
BCF:	0.455 ? 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:	3.019 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.485 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.698 ? 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
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	Leaf; Twig	n.a.	n.a.	PMID[30835120]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO507	Diplophyllum taxifolium	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10832	Pseudocalymma elegans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7173	Armillaria matsutake	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3225	Streptomyces garyphalus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15399	Phyllanthus meghalayensis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7173	Armillaria matsutake	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12256	Meconopsis quintuplinervia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16095	Euryspongia rosea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10832	Pseudocalymma elegans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12845	Podocarpus urbanii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15317	Desmos cochinchinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15399	Phyllanthus meghalayensis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3225	Streptomyces garyphalus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10520	Thunbergia fragrans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7173	Armillaria matsutake	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15426	Artemisia atrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO507	Diplophyllum taxifolium	Species	Scapaniaceae	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 NPC290771 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	16821
0.1-0.2	28827
0.2-0.3	3145
0.3-0.4	588
0.4-0.5	315
0.5-0.6	115
0.6-0.7	37
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7667	Intermediate Similarity	NPC209296
0.7667	Intermediate Similarity	NPC473327
0.7294	Intermediate Similarity	NPC191306
0.7191	Intermediate Similarity	NPC187379
0.6923	Remote Similarity	NPC173582
0.6923	Remote Similarity	NPC265885
0.6923	Remote Similarity	NPC181465
0.6923	Remote Similarity	NPC215710
0.6923	Remote Similarity	NPC473438
0.6923	Remote Similarity	NPC253788
0.6848	Remote Similarity	NPC22062
0.6848	Remote Similarity	NPC203259
0.6848	Remote Similarity	NPC473634
0.6848	Remote Similarity	NPC33054
0.6848	Remote Similarity	NPC210073
0.6848	Remote Similarity	NPC176740
0.6848	Remote Similarity	NPC471725
0.6848	Remote Similarity	NPC134532
0.6848	Remote Similarity	NPC138811
0.6848	Remote Similarity	NPC602582
0.6771	Remote Similarity	NPC476472
0.6771	Remote Similarity	NPC294815
0.6771	Remote Similarity	NPC16194
0.6739	Remote Similarity	NPC44931
0.6739	Remote Similarity	NPC39834
0.6421	Remote Similarity	NPC204693
0.6263	Remote Similarity	NPC477629
0.6168	Remote Similarity	NPC198199
0.6154	Remote Similarity	NPC219904
0.6122	Remote Similarity	NPC12013
0.6122	Remote Similarity	NPC11432
0.6122	Remote Similarity	NPC477613
0.61	Remote Similarity	NPC89127
0.6067	Remote Similarity	NPC143851
0.6064	Remote Similarity	NPC4390
0.6064	Remote Similarity	NPC600989
0.6061	Remote Similarity	NPC122467
0.6058	Remote Similarity	NPC173837
0.6044	Remote Similarity	NPC21100
0.6019	Remote Similarity	NPC89052
0.6	Remote Similarity	NPC120952
0.5979	Remote Similarity	NPC156869
0.5946	Remote Similarity	NPC192539
0.5938	Remote Similarity	NPC471079
0.5914	Remote Similarity	NPC601710
0.5882	Remote Similarity	NPC287889
0.5882	Remote Similarity	NPC221342
0.5882	Remote Similarity	NPC476470
0.5876	Remote Similarity	NPC67326
0.5865	Remote Similarity	NPC11468
0.5825	Remote Similarity	NPC602448
0.5806	Remote Similarity	NPC60735
0.5806	Remote Similarity	NPC26230
0.5758	Remote Similarity	NPC473571
0.5758	Remote Similarity	NPC110941
0.5745	Remote Similarity	NPC609478
0.5743	Remote Similarity	NPC473623
0.5729	Remote Similarity	NPC116864
0.5729	Remote Similarity	NPC244776
0.5728	Remote Similarity	NPC101636
0.5714	Remote Similarity	NPC254306
0.5714	Remote Similarity	NPC67105
0.57	Remote Similarity	NPC126784
0.57	Remote Similarity	NPC241423
0.57	Remote Similarity	NPC475366
0.57	Remote Similarity	NPC153755
0.5686	Remote Similarity	NPC488089
0.5684	Remote Similarity	NPC88023
0.5684	Remote Similarity	NPC309025
0.5676	Remote Similarity	NPC162394
0.566	Remote Similarity	NPC189564
0.5657	Remote Similarity	NPC65563
0.5657	Remote Similarity	NPC470949
0.5612	Remote Similarity	NPC609888
0.561	Remote Similarity	NPC52005
0.5607	Remote Similarity	NPC292019
0.5607	Remote Similarity	NPC202908
0.56	Remote Similarity	NPC186816
0.5566	Remote Similarity	NPC203145
0.5556	Remote Similarity	NPC473644
0.5556	Remote Similarity	NPC303694
0.5556	Remote Similarity	NPC227508
0.5505	Remote Similarity	NPC311850
0.549	Remote Similarity	NPC65711
0.5484	Remote Similarity	NPC265530
0.5446	Remote Similarity	NPC298666
0.5439	Remote Similarity	NPC241781
0.5437	Remote Similarity	NPC483707
0.5435	Remote Similarity	NPC111929
0.5435	Remote Similarity	NPC320283
0.5435	Remote Similarity	NPC41121
0.5424	Remote Similarity	NPC473554
0.5417	Remote Similarity	NPC22832
0.5417	Remote Similarity	NPC120099
0.5417	Remote Similarity	NPC605067
0.5376	Remote Similarity	NPC127546
0.5376	Remote Similarity	NPC57625
0.5376	Remote Similarity	NPC19709
0.5376	Remote Similarity	NPC173637
0.5376	Remote Similarity	NPC317489
0.5376	Remote Similarity	NPC223424
0.5376	Remote Similarity	NPC600591
0.5361	Remote Similarity	NPC223747
0.5357	Remote Similarity	NPC68592
0.5354	Remote Similarity	NPC254540
0.534	Remote Similarity	NPC470443
0.5333	Remote Similarity	NPC256760
0.5333	Remote Similarity	NPC85751
0.5333	Remote Similarity	NPC19240
0.5294	Remote Similarity	NPC129264
0.5283	Remote Similarity	NPC298171
0.5269	Remote Similarity	NPC135599
0.5269	Remote Similarity	NPC73855
0.5269	Remote Similarity	NPC331652
0.5269	Remote Similarity	NPC113968
0.5269	Remote Similarity	NPC328940
0.5269	Remote Similarity	NPC277174
0.5269	Remote Similarity	NPC606877
0.5263	Remote Similarity	NPC156785
0.5258	Remote Similarity	NPC181616
0.5253	Remote Similarity	NPC172807
0.5253	Remote Similarity	NPC211594
0.5234	Remote Similarity	NPC223426
0.5196	Remote Similarity	NPC303913
0.5189	Remote Similarity	NPC471669
0.5182	Remote Similarity	NPC477895
0.5164	Remote Similarity	NPC487502
0.5152	Remote Similarity	NPC476215
0.5149	Remote Similarity	NPC295613
0.5149	Remote Similarity	NPC473657
0.5143	Remote Similarity	NPC229409
0.514	Remote Similarity	NPC292929
0.514	Remote Similarity	NPC260504
0.514	Remote Similarity	NPC89809
0.5135	Remote Similarity	NPC217520
0.513	Remote Similarity	NPC474522
0.5106	Remote Similarity	NPC473043
0.51	Remote Similarity	NPC95866
0.5096	Remote Similarity	NPC470125
0.5096	Remote Similarity	NPC46202
0.5096	Remote Similarity	NPC64051
0.5094	Remote Similarity	NPC270675
0.5094	Remote Similarity	NPC195685
0.5088	Remote Similarity	NPC488086
0.5085	Remote Similarity	NPC262222
0.5083	Remote Similarity	NPC487499
0.5049	Remote Similarity	NPC473512
0.5049	Remote Similarity	NPC129827
0.5049	Remote Similarity	NPC605592
0.5047	Remote Similarity	NPC475382
0.5047	Remote Similarity	NPC473073
0.5046	Remote Similarity	NPC214621
0.5046	Remote Similarity	NPC34267
0.5046	Remote Similarity	NPC81042
0.5044	Remote Similarity	NPC488087
0.5043	Remote Similarity	NPC480445

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC290771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4883
0.1-0.2	4193
0.2-0.3	60
0.3-0.4	7
0.4-0.5	2
0.5-0.6	2
0.6-0.7	2
0.7-0.8	1
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
0.7667	Intermediate Similarity	NPD7054	Phase 4
0.6848	Remote Similarity	NPD6797	Phase 2
0.65	Remote Similarity	NPD7472	Pre-clinical
0.5278	Remote Similarity	NPD7808	Phase 3
0.5189	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