NPASS Compound

Natural Product: NPC294829

Natural Product ID	NPC294829
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QBWZGCGJFJZSIH-IHDBIPSSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 73 77 0 0 0 0 0 0 0 0999 V2000 -10.0697 3.3575 1.0216 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7165 3.5768 0.6702 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8205 2.5178 0.6782 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1757 1.2394 1.0148 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2196 0.2055 1.0038 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9144 0.4043 0.6668 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5697 1.7223 0.3246 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4989 2.7185 0.3370 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1250 4.0126 -0.0071 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8942 -0.6290 0.6404 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0439 -1.9489 0.9392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9971 -2.8644 0.8831 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1411 -4.0685 1.1575 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7627 -2.4135 0.5103 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6636 -3.2231 0.4206 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4548 -2.6944 0.0377 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2678 -1.3669 -0.2712 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4154 -0.5674 -0.1683 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6436 -1.0609 0.2120 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6649 -0.2539 0.2840 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9092 -0.7768 -0.6595 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1015 -1.4371 -0.8029 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6278 -1.3463 -2.2310 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8989 -2.0977 -2.3638 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6274 -2.4295 -1.1234 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0787 -1.8506 0.1547 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1382 -1.5156 1.1476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9332 -0.4505 0.8984 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3611 0.7844 0.8164 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6410 1.3208 -0.5703 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3680 2.7790 -0.6063 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5022 3.1955 0.5329 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0829 2.8088 1.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8933 1.6774 1.7664 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1881 2.8120 0.4132 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7507 3.0532 -1.8468 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9785 1.0211 -0.8754 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1435 -0.8498 -0.0338 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8117 -3.8206 -0.9843 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7385 -1.4403 -3.2946 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6188 -1.7838 -3.1006 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7623 -4.5652 0.7124 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2682 -2.4405 1.3181 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5996 4.2922 1.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0841 2.7536 1.9594 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5904 2.7338 0.2424 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1957 1.0302 1.2894 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5703 -0.7801 1.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5475 1.9322 0.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1388 4.7484 0.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4272 -3.3578 -0.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2908 0.4785 -0.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0846 -2.5168 -0.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7743 -0.2633 -2.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6423 -3.0671 -2.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6793 -2.0255 -1.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4887 -2.7019 0.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8160 -2.4096 1.3090 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6204 -1.4326 2.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2698 0.8333 0.9707 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9841 0.7365 -1.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3421 3.3151 -0.6227 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4977 4.3264 0.5334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6635 3.6102 2.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2329 2.5380 2.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6462 3.3923 1.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3991 3.9807 -1.8597 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0559 0.8909 -1.8610 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0160 -4.2553 -1.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4653 -0.4897 -3.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3929 -1.0917 -3.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9417 -5.0190 1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8431 -3.0431 0.7321 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 6 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 17 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 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 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 26 38 1 0 25 39 1 0 24 40 1 0 23 41 1 0 15 42 1 0 11 43 1 0 8 3 1 0 20 10 1 0 38 22 1 0 19 14 1 0 34 29 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 5 48 1 0 7 49 1 0 9 50 1 0 16 51 1 0 18 52 1 0 22 53 1 1 23 54 1 6 24 55 1 6 25 56 1 6 26 57 1 1 27 58 1 0 27 59 1 0 29 60 1 1 30 61 1 6 31 62 1 6 32 63 1 1 33 64 1 0 33 65 1 0 35 66 1 0 36 67 1 0 37 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	QBWZGCGJFJZSIH-IHDBIPSSSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-38-14-3-2-9(4-11(14)28)25-22(35)20(33)17-12(29)5-10(6-15(17)42-25)41-27-24(37)21(34)19(32)16(43-27)8-40-26-23(36)18(31)13(30)7-39-26/h2-6,13,16,18-19,21,23-24,26-32,34-37H,7-8H2,1H3/t13-,16+,18-,19+,21-,23+,24+,26+,27+/m0/s1
SMILES	COc1ccc(cc1O)c1c(c(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@@H]2[C@@H]([C@H]([C@H](CO2)O)O)O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	0.226 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.843 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.427 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.143	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.721	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:	0.639	Fluc inhibitor:	0.326 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.911 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.759 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.07	Promiscuous compounds:	0.543

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.457	MDCK Permeability:	-5.277
Pgp-inhibitor:	0.001	Pgp-substrate:	0.878
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):	0.562
20% Bioavailability (F20%):	0.007	30% Bioavailability (F30%):	0.932
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.053
Plasma Protein Binding (PPB):	79.264%	Volume Distribution (VD):	-0.342
Fu:	20.945% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.73
BSEP inhibitor:	0.033

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	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:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.149
HLM stability:	0.303 ? 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):

1.475

Half-life (T1/2):

4.742

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.172
Human Hepatotoxicity (H-HT):	0.545	Drug-induced Liver Injury (DILI):	0.976
AMES Toxicity:	0.934	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.07	Skin Sensitization:	0.992
Carcinogencity:	0.077	Eye Corrosion:	0.0
Eye Irritation:	0.695	Respiratory Toxicity:	0.028
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.917
Hematotoxicity:	0.281	Drug-induced Nephrotoxicity:	0.722
Genotoxicity:	0.913	RPMI-8226 Immunitoxicity:	0.238
A549 Cytotoxicity:	0.359	Hek293 Cytotoxicity:	0.302
BCF:	0.398 ? 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:	2.892 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.439 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.601 ? 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
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[16038562]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24784222]
NPO8673	Actinopyga echinites	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9041	Libocedrus formosana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14192	Climacoptera transoxana	Species	Tettigoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2961	Lomelosia caucasica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8261	Gleditsia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO382	Zanthoxylum scandens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13803	Neopetrosia exigua	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8673	Actinopyga echinites	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO931	Malus baccata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2961	Lomelosia caucasica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8261	Gleditsia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9041	Libocedrus formosana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14192	Climacoptera transoxana	Species	Tettigoniidae	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 NPC294829 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	19101
0.1-0.2	26740
0.2-0.3	3006
0.3-0.4	638
0.4-0.5	266
0.5-0.6	77
0.6-0.7	20
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
0.7111	Intermediate Similarity	NPC67105
0.7097	Intermediate Similarity	NPC209296
0.7011	Intermediate Similarity	NPC486578
0.6923	Remote Similarity	NPC275454
0.6923	Remote Similarity	NPC227508
0.6897	Remote Similarity	NPC285197
0.6633	Remote Similarity	NPC135358
0.6373	Remote Similarity	NPC480796
0.6316	Remote Similarity	NPC22062
0.6316	Remote Similarity	NPC473634
0.6316	Remote Similarity	NPC138811
0.6277	Remote Similarity	NPC187379
0.6263	Remote Similarity	NPC80068
0.6224	Remote Similarity	NPC51326
0.6076	Remote Similarity	NPC200740
0.6067	Remote Similarity	NPC108831
0.6067	Remote Similarity	NPC238376
0.6067	Remote Similarity	NPC182634
0.6061	Remote Similarity	NPC473327
0.6	Remote Similarity	NPC277205
0.6	Remote Similarity	NPC37919
0.6	Remote Similarity	NPC323593
0.6	Remote Similarity	NPC203500
0.5978	Remote Similarity	NPC611303
0.5957	Remote Similarity	NPC601586
0.5938	Remote Similarity	NPC295613
0.5938	Remote Similarity	NPC473657
0.5918	Remote Similarity	NPC186816
0.5914	Remote Similarity	NPC22832
0.59	Remote Similarity	NPC473623
0.5876	Remote Similarity	NPC44931
0.5859	Remote Similarity	NPC284277
0.5859	Remote Similarity	NPC475497
0.5859	Remote Similarity	NPC488074
0.5842	Remote Similarity	NPC488089
0.5816	Remote Similarity	NPC473512
0.5816	Remote Similarity	NPC129827
0.5816	Remote Similarity	NPC210073
0.58	Remote Similarity	NPC65711
0.5773	Remote Similarity	NPC471079
0.5714	Remote Similarity	NPC67326
0.5699	Remote Similarity	NPC21100
0.5631	Remote Similarity	NPC231194
0.5612	Remote Similarity	NPC51774
0.5586	Remote Similarity	NPC198199
0.5577	Remote Similarity	NPC287889
0.5567	Remote Similarity	NPC477848
0.5556	Remote Similarity	NPC15358
0.5545	Remote Similarity	NPC46202
0.551	Remote Similarity	NPC156977
0.55	Remote Similarity	NPC233994
0.5474	Remote Similarity	NPC307938
0.5464	Remote Similarity	NPC276377
0.5439	Remote Similarity	NPC120952
0.5437	Remote Similarity	NPC483707
0.5437	Remote Similarity	NPC606657
0.5429	Remote Similarity	NPC101636
0.5376	Remote Similarity	NPC254306
0.5361	Remote Similarity	NPC293004
0.5347	Remote Similarity	NPC479405
0.5347	Remote Similarity	NPC303913
0.534	Remote Similarity	NPC211532
0.534	Remote Similarity	NPC488364
0.5327	Remote Similarity	NPC244875
0.5321	Remote Similarity	NPC472993
0.53	Remote Similarity	NPC236191
0.5294	Remote Similarity	NPC204693
0.5294	Remote Similarity	NPC479404
0.5283	Remote Similarity	NPC235575
0.5278	Remote Similarity	NPC11468
0.5263	Remote Similarity	NPC229687
0.5263	Remote Similarity	NPC181712
0.5248	Remote Similarity	NPC301683
0.5243	Remote Similarity	NPC64051
0.5238	Remote Similarity	NPC142142
0.5238	Remote Similarity	NPC270675
0.5238	Remote Similarity	NPC195685
0.52	Remote Similarity	NPC251417
0.5192	Remote Similarity	NPC479403
0.5189	Remote Similarity	NPC476472
0.5189	Remote Similarity	NPC294815
0.5189	Remote Similarity	NPC16194
0.5158	Remote Similarity	NPC95090
0.5158	Remote Similarity	NPC27408
0.5143	Remote Similarity	NPC229409
0.514	Remote Similarity	NPC298171
0.5138	Remote Similarity	NPC121703
0.5135	Remote Similarity	NPC25523
0.5104	Remote Similarity	NPC46420
0.5102	Remote Similarity	NPC243930
0.51	Remote Similarity	NPC52353
0.5098	Remote Similarity	NPC142996
0.5094	Remote Similarity	NPC486577
0.5093	Remote Similarity	NPC472994
0.5053	Remote Similarity	NPC289667
0.5052	Remote Similarity	NPC27942
0.5051	Remote Similarity	NPC607707
0.5048	Remote Similarity	NPC470443
0.5046	Remote Similarity	NPC603856
0.5044	Remote Similarity	NPC488087

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC294829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4975
0.1-0.2	4112
0.2-0.3	47
0.3-0.4	11
0.4-0.5	1
0.5-0.6	3
0.6-0.7	0
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
0.7097	Intermediate Similarity	NPD7054	Phase 4
0.5714	Remote Similarity	NPD7472	Pre-clinical
0.5714	Remote Similarity	NPD7808	Phase 3
0.5481	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