NPASS Compound

Natural Product: NPC273032

Natural Product ID	NPC273032
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HCCQMPYJVVKWJT-QXGRHDLQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	13648575
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 69 72 0 0 0 0 0 0 0 0999 V2000 -2.4197 5.4279 -0.7603 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1222 5.9010 -0.4787 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0110 5.1164 -0.2881 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0798 3.7350 -0.3574 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0316 2.9507 -0.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2178 3.5920 0.0959 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3082 4.9723 0.1695 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1879 5.7415 -0.0235 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2683 7.1463 0.0483 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9734 1.4740 -0.2328 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2791 0.8160 1.0608 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2211 0.5796 2.0605 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8537 -0.1581 1.8386 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8561 0.1204 0.9929 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0181 -0.9552 -0.0584 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9147 -0.2880 -1.1155 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2608 -0.2039 -0.4408 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2199 0.0936 1.0004 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9936 -0.9596 1.8143 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2001 -1.2738 1.2205 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0767 0.3283 1.6442 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0694 0.6468 -1.1946 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9149 -1.0637 -2.2470 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8671 -1.3936 -0.6239 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9380 -0.4468 0.5608 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0749 -1.6561 1.1478 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7297 -2.6830 0.4542 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8624 -3.9723 1.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4648 -4.9839 0.4998 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5530 -6.2789 1.2432 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8890 -7.2200 0.4615 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2285 -2.4714 -0.8031 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0813 -1.2307 -1.3903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4298 -0.2040 -0.7035 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1471 1.1168 -1.0475 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5824 -1.0196 -2.6484 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2491 -2.0179 -3.3877 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1351 6.2753 -0.8099 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7260 4.7460 0.0633 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3963 4.9153 -1.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0425 3.2486 -0.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1292 3.0364 0.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2398 5.4785 0.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1639 7.5778 -0.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1427 1.1001 -0.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1510 1.4020 1.5532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0430 1.5725 2.5887 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7756 0.0678 2.9451 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6735 1.0779 0.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6297 -1.7625 0.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5607 0.7464 -1.2760 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7143 -1.2324 -0.5736 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8608 1.0244 1.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2397 -0.5400 2.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3919 -1.8545 2.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2535 -2.2408 0.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9925 0.2880 -1.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6460 -1.7360 -2.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8756 -1.4451 -1.5908 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7014 -1.8752 2.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4455 -4.0918 2.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8948 -4.9355 -0.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1274 -6.1978 2.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6235 -6.5234 1.3510 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9562 -7.3333 0.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7462 -3.2342 -1.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6557 -2.9541 -3.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3502 -1.6566 -4.4518 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2387 -2.2218 -2.9554 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 8 9 1 0 5 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 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 17 22 1 0 16 23 1 0 15 24 1 0 11 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 27 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 33 36 1 0 36 37 1 0 8 3 1 0 35 10 1 0 21 14 1 0 34 25 1 0 1 38 1 0 1 39 1 0 1 40 1 0 4 41 1 0 6 42 1 0 7 43 1 0 9 44 1 0 10 45 1 6 11 46 1 1 12 47 1 0 12 48 1 0 14 49 1 6 15 50 1 1 16 51 1 6 17 52 1 1 18 53 1 6 19 54 1 0 19 55 1 0 20 56 1 0 22 57 1 0 23 58 1 0 24 59 1 0 26 60 1 0 28 61 1 0 29 62 1 0 30 63 1 0 30 64 1 0 31 65 1 0 32 66 1 0 37 67 1 0 37 68 1 0 37 69 1 0 M END

Standard InCHIKey	HCCQMPYJVVKWJT-QXGRHDLQSA-N
Standard InCHI	InChI=1S/C26H32O11/c1-33-18-10-14(5-6-17(18)29)24-16(12-35-26-23(32)22(31)21(30)20(11-28)36-26)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h3-6,8-10,16,20-24,26-32H,7,11-12H2,1-2H3/b4-3+/t16-,20+,21+,22-,23+,24+,26+/m0/s1
SMILES	COc1cc(ccc1O)[C@@H]1[C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)c2cc(/C=C/CO)cc(c2O1)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	520.19	Volume:	502.264 ? Van der Waals volume.
Dense:	1.036	LogP:	1.131 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.704 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.356 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	167.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.446	Fsp³:	0.462
MCE-18:	87.579 ? 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:	0.463	Fluc inhibitor:	0.35 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.071 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.801 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.107	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.955	MDCK Permeability:	-5.258
Pgp-inhibitor:	0.014	Pgp-substrate:	0.229
PAMPA:	0.245 ? 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):	0.399
20% Bioavailability (F20%):	0.784	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.067
Plasma Protein Binding (PPB):	71.651%	Volume Distribution (VD):	-0.325
Fu:	27.595% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.593
BSEP inhibitor:	0.261

ADMET: Metabolism

CYP1A2-inhibitor:	0.078	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.351	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.177
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.734
HLM stability:	0.071 ? 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):

2.779

Half-life (T1/2):

2.787

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.09
Human Hepatotoxicity (H-HT):	0.849	Drug-induced Liver Injury (DILI):	0.58
AMES Toxicity:	0.817	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	0.995
Carcinogencity:	0.194	Eye Corrosion:	0.0
Eye Irritation:	0.263	Respiratory Toxicity:	0.07
Drug-induced Neurotoxicity:	0.098	Ototoxicity:	0.949
Hematotoxicity:	0.269	Drug-induced Nephrotoxicity:	0.64
Genotoxicity:	0.313	RPMI-8226 Immunitoxicity:	0.177
A549 Cytotoxicity:	0.759	Hek293 Cytotoxicity:	0.438
BCF:	0.523 ? 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:	3.038 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.026 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.81 ? 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
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO27759	Fusarium poae	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37371939]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37569477]
NPO27022	Neisseria meningitidis	Species	Neisseriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4990768]
NPO27523	Brickellia glutinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6436442]
NPO27177	Telitoxicum glaziovii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29171	Ascochyta salicorniae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27523	Brickellia glutinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27759	Fusarium poae	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8618	Hypotrachyna cirrhata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27022	Neisseria meningitidis	Species	Neisseriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27536	Sidastrum quinquenervium	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27022	Neisseria meningitidis	Species	Neisseriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27759	Fusarium poae	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27523	Brickellia glutinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29171	Ascochyta salicorniae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27177	Telitoxicum glaziovii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8618	Hypotrachyna cirrhata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27536	Sidastrum quinquenervium	Species	Malvaceae	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 NPC273032 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	19786
0.1-0.2	25072
0.2-0.3	4078
0.3-0.4	780
0.4-0.5	92
0.5-0.6	40
0.6-0.7	7
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
0.7531	Intermediate Similarity	NPC114505
0.7531	Intermediate Similarity	NPC213074
0.725	Intermediate Similarity	NPC478701
0.6628	Remote Similarity	NPC15956
0.6512	Remote Similarity	NPC302610
0.6129	Remote Similarity	NPC479449
0.6067	Remote Similarity	NPC224674
0.6067	Remote Similarity	NPC64475
0.6053	Remote Similarity	NPC156502
0.6053	Remote Similarity	NPC10737
0.5977	Remote Similarity	NPC193473
0.5977	Remote Similarity	NPC600128
0.5938	Remote Similarity	NPC98624
0.5926	Remote Similarity	NPC131971
0.5926	Remote Similarity	NPC15189
0.5926	Remote Similarity	NPC480707
0.5882	Remote Similarity	NPC469559
0.5862	Remote Similarity	NPC43508
0.5814	Remote Similarity	NPC270751
0.573	Remote Similarity	NPC472710
0.573	Remote Similarity	NPC472709
0.5652	Remote Similarity	NPC269559
0.56	Remote Similarity	NPC228357
0.557	Remote Similarity	NPC307110
0.5556	Remote Similarity	NPC253878
0.5495	Remote Similarity	NPC479448
0.5455	Remote Similarity	NPC236166
0.5455	Remote Similarity	NPC480698
0.5375	Remote Similarity	NPC157554
0.5366	Remote Similarity	NPC206413
0.5366	Remote Similarity	NPC482649
0.5366	Remote Similarity	NPC149003
0.5366	Remote Similarity	NPC471414
0.5366	Remote Similarity	NPC482647
0.5366	Remote Similarity	NPC482648
0.5366	Remote Similarity	NPC482651
0.5366	Remote Similarity	NPC194244
0.5366	Remote Similarity	NPC482650
0.5341	Remote Similarity	NPC216916
0.5341	Remote Similarity	NPC45943
0.5341	Remote Similarity	NPC469889
0.5128	Remote Similarity	NPC187616
0.5128	Remote Similarity	NPC193026
0.5128	Remote Similarity	NPC49603
0.5122	Remote Similarity	NPC284881
0.5122	Remote Similarity	NPC93433
0.5122	Remote Similarity	NPC474444
0.5063	Remote Similarity	NPC87725
0.5063	Remote Similarity	NPC263261
0.5049	Remote Similarity	NPC241600

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC273032 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5124
0.1-0.2	3932
0.2-0.3	89
0.3-0.4	5
0.4-0.5	0
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