NPASS Compound

Natural Product: NPC134776

Natural Product ID	NPC134776
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DMAQFLQMQDZICP-LMIKHVAYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5315793
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 85 90 0 0 0 0 0 0 0 0999 V2000 -4.3260 4.5878 1.6845 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1159 5.9331 1.9799 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7786 6.8997 1.2962 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6595 6.5228 0.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8564 5.2074 0.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1657 4.1551 0.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4218 2.8638 0.1829 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6000 1.8914 0.0433 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2311 1.8422 0.3802 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5779 2.7989 0.8575 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5459 0.6319 0.1668 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1670 0.6052 0.5342 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5877 -0.7044 0.1273 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2776 -1.9262 0.7331 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2819 -3.0935 0.6180 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5815 -2.8904 -0.6267 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3140 -1.6183 -0.5643 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6685 -1.5806 -0.5981 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6411 -0.8550 -0.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5057 -0.0186 1.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5879 0.6904 1.6012 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8448 0.5994 1.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8829 1.3245 1.6035 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7393 2.0746 2.5934 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1237 1.1641 0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2469 0.3358 -0.1160 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5486 0.1736 -0.7868 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6888 0.7808 -0.3483 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9175 0.6398 -1.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0017 -0.1263 -2.1429 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8405 -0.7507 -2.5969 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6311 -0.6080 -1.9349 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1644 -0.3370 -2.8846 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1903 -0.3112 -0.5544 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9930 -0.2315 -0.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9191 -0.9417 -0.5547 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4210 1.5234 2.7091 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7681 -0.7810 0.4962 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3556 -2.8858 -1.6942 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 -3.2353 1.7794 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4113 -2.2864 0.0055 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7337 -2.2498 0.4406 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9419 -1.8360 1.6024 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8318 -2.6736 -0.4198 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0548 -2.5817 0.0258 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2237 -2.9758 -0.7359 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1190 -3.5595 -1.9500 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2178 -3.9376 -2.7382 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4639 -3.6902 -2.2245 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6319 -3.0942 -0.9838 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5186 -2.7485 -0.2644 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5927 -4.0304 -2.9354 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5998 8.2645 1.5577 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8448 3.8500 2.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4130 6.2071 2.7587 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1856 7.3277 -0.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5506 4.9414 -0.7396 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4939 2.6847 -0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0311 0.9427 -0.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0518 0.7412 1.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6588 1.4279 -0.0026 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6187 -0.7615 -0.9898 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4239 -1.6698 1.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8846 -4.0076 0.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1554 -3.8071 -0.7840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9698 -0.9462 -1.4407 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5539 0.0826 1.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9549 1.7272 1.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6905 1.4076 0.5474 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8065 1.1305 -0.6515 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8730 -1.3717 -3.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7236 -1.0826 -2.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1989 -1.1290 -3.5503 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0781 -1.5896 -1.4330 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5142 1.0595 3.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1989 -3.5787 -2.3540 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6300 -2.3908 2.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6475 -3.0549 -1.4042 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2443 -2.1750 1.0450 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1421 -3.7658 -2.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0895 -4.4035 -3.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6417 -2.9207 -0.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6137 -2.2768 0.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6312 -4.4243 -3.8560 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1689 8.8739 0.8932 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 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 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 26 34 1 0 34 35 1 0 35 36 2 0 21 37 1 0 17 38 1 0 16 39 1 0 15 40 1 0 14 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 49 52 1 0 3 53 1 0 6 1 1 0 38 13 1 0 51 46 1 0 36 19 1 0 35 22 1 0 32 27 1 0 1 54 1 0 2 55 1 0 4 56 1 0 5 57 1 0 7 58 1 0 8 59 1 0 12 60 1 0 12 61 1 0 13 62 1 6 14 63 1 1 15 64 1 6 16 65 1 6 17 66 1 6 20 67 1 0 25 68 1 0 28 69 1 0 29 70 1 0 31 71 1 0 32 72 1 0 33 73 1 0 36 74 1 0 37 75 1 0 39 76 1 0 40 77 1 0 44 78 1 0 45 79 1 0 47 80 1 0 48 81 1 0 50 82 1 0 51 83 1 0 52 84 1 0 53 85 1 0 M END

Standard InCHIKey	DMAQFLQMQDZICP-LMIKHVAYSA-N
Standard InCHI	InChI=1S/C39H32O14/c40-24-9-1-21(2-10-24)5-15-33(45)49-20-32-38(53-34(46)16-6-22-3-11-25(41)12-4-22)36(47)37(48)39(52-32)50-27-17-28(43)35-29(44)19-30(51-31(35)18-27)23-7-13-26(42)14-8-23/h1-19,32,36-43,47-48H,20H2/b15-5-,16-6+/t32-,36-,37-,38-,39-/m1/s1
SMILES	c1cc(ccc1/C=CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc(c3c(=O)cc(c4ccc(cc4)O)oc3c2)O)O1)O)O)OC(=O)/C=C/c1ccc(cc1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	724.18	Volume:	707.368 ? Van der Waals volume.
Dense:	1.024	LogP:	3.255 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.803 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.04 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	40.0
TPSA:	222.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.44	Fsp³:	0.154
MCE-18:	119.222 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.971 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.99 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.324	Promiscuous compounds:	0.648

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.038	MDCK Permeability:	-4.985
Pgp-inhibitor:	0.024	Pgp-substrate:	0.001
PAMPA:	0.977 ? 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%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.002
Plasma Protein Binding (PPB):	92.553%	Volume Distribution (VD):	-0.027
Fu:	8.376% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.017
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.029
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.029 ? 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):

2.958

Half-life (T1/2):

3.219

ADMET: Toxicity

hERG Blockers:	0.37	hERG Blockers (10um):	0.774
Human Hepatotoxicity (H-HT):	0.56	Drug-induced Liver Injury (DILI):	0.857
AMES Toxicity:	0.555	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.835	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.835	Respiratory Toxicity:	0.098
Drug-induced Neurotoxicity:	0.052	Ototoxicity:	0.214
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.276
Genotoxicity:	0.883	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.978	Hek293 Cytotoxicity:	0.992
BCF:	0.965 ? 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:	4.396 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.128 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.023 ? 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
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872152]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31994397]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16560	Palhinhaea cernua	Species	Lycopodiaceae	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 NPC134776 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	15893
0.1-0.2	29509
0.2-0.3	3462
0.3-0.4	736
0.4-0.5	189
0.5-0.6	52
0.6-0.7	8
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
0.7935	Intermediate Similarity	NPC270675
0.7935	Intermediate Similarity	NPC195685
0.75	Intermediate Similarity	NPC472994
0.732	Intermediate Similarity	NPC179862
0.72	Intermediate Similarity	NPC472993
0.72	Intermediate Similarity	NPC473278
0.697	Remote Similarity	NPC484301
0.6907	Remote Similarity	NPC210961
0.66	Remote Similarity	NPC80068
0.6422	Remote Similarity	NPC471030
0.6275	Remote Similarity	NPC477629
0.6237	Remote Similarity	NPC27942
0.6058	Remote Similarity	NPC260504
0.6058	Remote Similarity	NPC89809
0.5978	Remote Similarity	NPC331652
0.5962	Remote Similarity	NPC188815
0.5926	Remote Similarity	NPC480796
0.5922	Remote Similarity	NPC139060
0.5914	Remote Similarity	NPC39360
0.5914	Remote Similarity	NPC29763
0.5914	Remote Similarity	NPC210003
0.5882	Remote Similarity	NPC64051
0.5755	Remote Similarity	NPC298171
0.5743	Remote Similarity	NPC44931
0.5727	Remote Similarity	NPC164704
0.5726	Remote Similarity	NPC199172
0.5657	Remote Similarity	NPC190003
0.5619	Remote Similarity	NPC104883
0.5619	Remote Similarity	NPC488679
0.5607	Remote Similarity	NPC101636
0.5565	Remote Similarity	NPC156785
0.5524	Remote Similarity	NPC477628
0.5464	Remote Similarity	NPC181712
0.5446	Remote Similarity	NPC470715
0.5431	Remote Similarity	NPC474522
0.5429	Remote Similarity	NPC472992
0.537	Remote Similarity	NPC85751
0.537	Remote Similarity	NPC19240
0.5351	Remote Similarity	NPC470716
0.5327	Remote Similarity	NPC229409
0.5278	Remote Similarity	NPC488089
0.5258	Remote Similarity	NPC19709
0.5204	Remote Similarity	NPC95090
0.5204	Remote Similarity	NPC27408
0.5204	Remote Similarity	NPC189142
0.5204	Remote Similarity	NPC77660
0.5182	Remote Similarity	NPC36138
0.5169	Remote Similarity	NPC470717
0.5164	Remote Similarity	NPC35924
0.5149	Remote Similarity	NPC601144
0.514	Remote Similarity	NPC46202
0.5135	Remote Similarity	NPC223426
0.5135	Remote Similarity	NPC218161
0.5126	Remote Similarity	NPC470720
0.5116	Remote Similarity	NPC234133
0.5098	Remote Similarity	NPC311830
0.5094	Remote Similarity	NPC22062
0.5094	Remote Similarity	NPC473634
0.5094	Remote Similarity	NPC210073
0.5094	Remote Similarity	NPC138811
0.5089	Remote Similarity	NPC96605
0.5089	Remote Similarity	NPC280642
0.505	Remote Similarity	NPC282169
0.5047	Remote Similarity	NPC122809
0.5046	Remote Similarity	NPC473623
0.5044	Remote Similarity	NPC599948

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4205
0.1-0.2	4857
0.2-0.3	77
0.3-0.4	10
0.4-0.5	1
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