NPASS Compound

Natural Product: NPC271317

Natural Product ID	NPC271317
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TXGMSHTWMBVGQZ-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102115497
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 61 66 0 0 0 0 0 0 0 0999 V2000 -1.8716 -3.6267 -3.1863 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2796 -3.0682 -2.0328 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2487 -2.1774 -2.1662 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1985 -1.8367 -3.4218 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2305 -0.9455 -3.5718 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7975 -0.4097 -2.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8350 0.4879 -2.5518 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2848 0.8359 -3.6742 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3529 0.9833 -1.3653 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8606 0.6022 -0.1389 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4234 1.1395 1.1219 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4525 2.0359 1.1741 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9572 2.5190 2.3397 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4387 2.1147 3.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3960 1.2078 3.5322 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8901 0.7226 2.3412 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9584 2.6117 4.7375 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8667 -0.2596 -0.0893 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3512 -0.7495 -1.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3035 -1.6534 -1.0108 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1748 -2.0183 0.3145 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3333 -3.0772 1.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1088 -3.4304 2.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1281 -2.6939 2.8800 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6531 -1.6284 2.1782 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6594 -0.8810 2.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1537 -1.0967 3.8700 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1462 0.1868 1.9695 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6561 0.4812 0.7286 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1476 1.5927 -0.0963 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1452 2.4107 0.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6136 3.4709 -0.4421 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0735 3.7072 -1.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0673 2.8608 -2.0942 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5872 1.8183 -1.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5277 4.7612 -2.4819 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 -0.2848 0.2406 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1959 -1.2880 0.9237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6181 -3.0012 4.1400 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3500 -3.8295 0.4649 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7122 -0.5751 -4.8345 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2195 -4.3354 -3.7159 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8466 -4.0717 -2.8737 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1421 -2.8151 -3.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2282 -2.2426 -4.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1665 1.6868 -1.4572 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8980 2.3881 0.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7878 3.2422 2.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9889 0.8908 4.4978 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0725 0.0117 2.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6029 3.3694 4.7174 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3075 -4.2643 2.8232 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9537 0.8047 2.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6190 2.2822 1.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4024 4.1006 -0.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6344 3.0525 -3.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7996 1.1581 -1.6796 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5301 4.8939 -2.6427 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5661 -3.3663 4.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2780 -3.9030 0.9037 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5795 -0.9016 -5.1993 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 14 17 1 0 10 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 29 37 1 0 37 38 1 0 24 39 1 0 22 40 1 0 5 41 1 0 20 3 1 0 38 21 1 0 19 6 1 0 38 25 2 0 16 11 1 0 35 30 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 9 46 1 0 12 47 1 0 13 48 1 0 15 49 1 0 16 50 1 0 17 51 1 0 23 52 1 0 28 53 1 0 31 54 1 0 32 55 1 0 34 56 1 0 35 57 1 0 36 58 1 0 39 59 1 0 40 60 1 0 41 61 1 0 M END

Standard InCHIKey	TXGMSHTWMBVGQZ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C31H20O10/c1-39-25-13-22(38)27-21(37)12-24(15-4-8-17(33)9-5-15)41-31(27)29(25)28-19(35)10-18(34)26-20(36)11-23(40-30(26)28)14-2-6-16(32)7-3-14/h2-13,32-35,38H,1H3
SMILES	COc1cc(c2c(=O)cc(c3ccc(cc3)O)oc2c1c1c(cc(c2c(=O)cc(c3ccc(cc3)O)oc12)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.11	Volume:	539.112 ? Van der Waals volume.
Dense:	1.024	LogP:	4.372 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.503 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.983 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	36.0
TPSA:	170.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.19	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.045	Fsp³:	0.032
MCE-18:	36.0 ? 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:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.995	Fluc inhibitor:	0.236 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.961 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.995 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.406	Promiscuous compounds:	0.934

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007	MDCK Permeability:	-4.771
Pgp-inhibitor:	0.006	Pgp-substrate:	0.387
PAMPA:	0.514 ? 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):	0.0
20% Bioavailability (F20%):	0.091	30% Bioavailability (F30%):	0.587
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.748
Plasma Protein Binding (PPB):	96.795%	Volume Distribution (VD):	-0.462
Fu:	3.204% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.958
OATP1B3 inhibitor:	0.937	BCRP inhibitor:	0.795
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.769	CYP2C9-substrate:	0.532
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.131
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.755 ? 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):

2.3

Half-life (T1/2):

1.99

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.48
Human Hepatotoxicity (H-HT):	0.498	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.699	Rat Oral Acute Toxicity:	0.579
Maximum Recommended Daily Dose:	0.968	Skin Sensitization:	0.601
Carcinogencity:	0.848	Eye Corrosion:	0.001
Eye Irritation:	0.981	Respiratory Toxicity:	0.878
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.062
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.018
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.657	Hek293 Cytotoxicity:	0.973
BCF:	1.143 ? 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:	4.313 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.614 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.383 ? 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
NPO23434	Fissistigma latifolium	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29160716]
NPO24272	Akania lucens	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22365	Osbeckia chinensis	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23575	Aspergillus restrictus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23434	Fissistigma latifolium	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13513	Agathis palmerstonii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20124	Xylopia discreta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11353	Viscaria vulgaris	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22365	Osbeckia chinensis	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20124	Xylopia discreta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24155	Nepeta annua	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23153	Eria smithii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24351	Sclerotinia libertiana	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23575	Aspergillus restrictus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11353	Viscaria vulgaris	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7689	Cota triumfettii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25084	Dasiphora fruticosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24234	Agrocybe aegerita	Species	Bolbitiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23434	Fissistigma latifolium	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13513	Agathis palmerstonii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24272	Akania lucens	Species	Akaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22216	Chimonanthus fragrans	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24429	Cestrum pallidissimum	Species	Solanaceae	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 NPC271317 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	30510
0.1-0.2	16327
0.2-0.3	2163
0.3-0.4	667
0.4-0.5	141
0.5-0.6	31
0.6-0.7	14
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	Natural Product ID
0.7458	Intermediate Similarity	NPC610914
0.7407	Intermediate Similarity	NPC222713
0.7164	Intermediate Similarity	NPC290830
0.6812	Remote Similarity	NPC194593
0.6714	Remote Similarity	NPC215203
0.661	Remote Similarity	NPC52611
0.6528	Remote Similarity	NPC265624
0.6522	Remote Similarity	NPC603508
0.6429	Remote Similarity	NPC71061
0.6389	Remote Similarity	NPC601565
0.6351	Remote Similarity	NPC55443
0.6286	Remote Similarity	NPC601984
0.625	Remote Similarity	NPC67322
0.6119	Remote Similarity	NPC288840
0.6111	Remote Similarity	NPC159707
0.6066	Remote Similarity	NPC301323
0.6027	Remote Similarity	NPC121649
0.5972	Remote Similarity	NPC303485
0.597	Remote Similarity	NPC138299
0.5968	Remote Similarity	NPC234133
0.589	Remote Similarity	NPC186227
0.5753	Remote Similarity	NPC158027
0.5714	Remote Similarity	NPC254351
0.5676	Remote Similarity	NPC14606
0.5616	Remote Similarity	NPC150908
0.557	Remote Similarity	NPC604941
0.5556	Remote Similarity	NPC241498
0.5556	Remote Similarity	NPC606549
0.5526	Remote Similarity	NPC18699
0.55	Remote Similarity	NPC50898
0.5443	Remote Similarity	NPC607079
0.5397	Remote Similarity	NPC607196
0.5357	Remote Similarity	NPC66441
0.5312	Remote Similarity	NPC71334
0.5312	Remote Similarity	NPC275836
0.5312	Remote Similarity	NPC47815
0.527	Remote Similarity	NPC248739
0.5231	Remote Similarity	NPC231772
0.5231	Remote Similarity	NPC198826
0.5231	Remote Similarity	NPC231018
0.5231	Remote Similarity	NPC120163
0.52	Remote Similarity	NPC600972
0.5161	Remote Similarity	NPC296197
0.5152	Remote Similarity	NPC159275
0.5152	Remote Similarity	NPC78913
0.5147	Remote Similarity	NPC183950
0.5135	Remote Similarity	NPC259757
0.5132	Remote Similarity	NPC72425

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC271317 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6053
0.1-0.2	3041
0.2-0.3	49
0.3-0.4	5
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
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
		NPD

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