NPASS Compound

Natural Product: NPC17350

Natural Product ID	NPC17350
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LSXRXFWRYBBFTA-BJBZVNFPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	100998069
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 7.1166 -1.2231 1.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9118 -1.2442 0.2699 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4367 -1.2746 -1.1212 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4377 -1.7208 -2.1480 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4507 -2.7191 -1.6189 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9670 -2.2214 -0.2734 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0850 -2.3055 0.5895 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6331 -0.8714 -0.3577 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4438 -0.2789 -0.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3243 -0.9393 0.4287 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1499 -0.2388 0.7406 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0526 1.1040 0.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1882 1.7768 0.1474 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3288 1.0933 -0.1548 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4241 1.8156 -0.6108 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1471 1.9103 0.8655 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3645 1.3238 0.9625 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4399 2.1985 1.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5956 1.7388 1.3216 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2835 3.5529 1.3506 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3339 4.4126 1.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1338 5.7737 1.7254 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8606 6.2948 1.6089 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8274 5.4186 1.3644 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9895 4.0552 1.2293 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0037 3.2363 0.9984 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6421 7.6786 1.7391 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5997 3.8880 1.7104 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7041 0.0066 0.8401 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1659 -0.5494 -0.3933 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4738 -1.7773 -0.8491 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5005 -2.6840 -1.5469 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3985 -3.1725 -0.4189 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8045 -1.9855 0.4426 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2438 -2.0665 0.8745 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5182 -0.7951 -0.2261 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7525 -4.1569 0.2747 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1994 -1.8581 -2.4221 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4130 -1.5226 -1.7231 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1301 -3.9355 -1.4056 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1301 -2.3543 -3.2013 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9203 -0.0060 -1.4407 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5849 -0.2074 1.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8499 -1.9603 0.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7926 -1.3892 2.2469 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3423 -0.2986 0.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3234 -1.9621 -1.1679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9624 -0.8309 -2.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6342 -2.8655 -2.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1473 -2.8635 0.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3581 -1.9968 0.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6863 -0.7995 1.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1178 2.8481 0.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2540 2.5027 -1.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9426 6.4741 1.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8252 5.8311 1.2725 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5643 8.1825 0.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4137 4.4858 1.7575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1050 0.2184 -1.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1347 -2.3605 0.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0382 -3.5458 -2.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3183 -3.5702 -0.8810 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1712 -2.0160 1.3457 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3779 -2.6736 1.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7726 -2.6576 0.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7113 -1.0667 1.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2921 -4.7420 -0.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1696 -1.9504 -2.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5766 -0.6607 -2.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8654 -3.7705 -0.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1062 -2.2983 -3.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0261 0.5656 -0.6280 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 6 8 1 0 8 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 12 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 23 27 1 0 21 28 1 0 17 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 33 37 1 0 32 38 1 0 31 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 7 2 1 0 14 9 1 0 26 16 1 0 36 30 1 0 25 20 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 3 47 1 1 4 48 1 6 5 49 1 6 6 50 1 1 10 51 1 0 11 52 1 0 13 53 1 0 15 54 1 0 22 55 1 0 24 56 1 0 27 57 1 0 28 58 1 0 30 59 1 6 31 60 1 1 32 61 1 6 33 62 1 6 34 63 1 1 35 64 1 0 35 65 1 0 35 66 1 0 37 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	LSXRXFWRYBBFTA-BJBZVNFPSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-8-17(31)20(34)22(36)26(38-8)41-14-4-3-10(5-12(14)29)24-25(42-27-23(37)21(35)18(32)9(2)39-27)19(33)16-13(30)6-11(28)7-15(16)40-24/h3-9,17-18,20-23,26-32,34-37H,1-2H3/t8-,9-,17-,18-,20+,21+,22+,23+,26-,27-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1ccc(cc1O)c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	1.332 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.633 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.437 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	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:	0.172	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.759	Fsp³:	0.444
MCE-18:	122.949 ? 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:	0.642	Fluc inhibitor:	0.297 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.812 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.507 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.231	Promiscuous compounds:	0.576

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.358	MDCK Permeability:	-5.083
Pgp-inhibitor:	0.0	Pgp-substrate:	0.954
PAMPA:	1.0 ? 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):	0.209
20% Bioavailability (F20%):	0.28	30% Bioavailability (F30%):	0.982
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.05
Plasma Protein Binding (PPB):	86.072%	Volume Distribution (VD):	-0.056
Fu:	13.751% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.957
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.701
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.017	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.951
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.963 ? 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):

1.875

Half-life (T1/2):

5.366

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.248
Human Hepatotoxicity (H-HT):	0.399	Drug-induced Liver Injury (DILI):	0.918
AMES Toxicity:	0.838	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.051	Skin Sensitization:	0.98
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.406	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.888
Hematotoxicity:	0.057	Drug-induced Nephrotoxicity:	0.331
Genotoxicity:	0.818	RPMI-8226 Immunitoxicity:	0.227
A549 Cytotoxicity:	0.518	Hek293 Cytotoxicity:	0.537
BCF:	0.565 ? 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:	3.254 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.643 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.848 ? 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
NPO29658	Spinulum annotinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29658	Spinulum annotinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO376	Suillus tridentinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29658	Spinulum annotinum	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 NPC17350 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	16393
0.1-0.2	29989
0.2-0.3	2453
0.3-0.4	552
0.4-0.5	203
0.5-0.6	87
0.6-0.7	87
0.7-0.8	0
0.8-0.85	12
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC219904
0.8493	Intermediate Similarity	NPC60735
0.8493	Intermediate Similarity	NPC26230
0.8194	Intermediate Similarity	NPC127546
0.8194	Intermediate Similarity	NPC57625
0.8194	Intermediate Similarity	NPC173637
0.8194	Intermediate Similarity	NPC317489
0.8194	Intermediate Similarity	NPC223424
0.8194	Intermediate Similarity	NPC600591
0.8082	Intermediate Similarity	NPC265530
0.8056	Intermediate Similarity	NPC111929
0.8056	Intermediate Similarity	NPC320283
0.8056	Intermediate Similarity	NPC41121
0.7895	Intermediate Similarity	NPC120099
0.7895	Intermediate Similarity	NPC609478
0.7808	Intermediate Similarity	NPC135599
0.7808	Intermediate Similarity	NPC73855
0.7808	Intermediate Similarity	NPC113968
0.7808	Intermediate Similarity	NPC328940
0.7808	Intermediate Similarity	NPC277174
0.7808	Intermediate Similarity	NPC606877
0.7792	Intermediate Similarity	NPC223747
0.7711	Intermediate Similarity	NPC473327
0.7308	Intermediate Similarity	NPC611303
0.7284	Intermediate Similarity	NPC251417
0.7143	Intermediate Similarity	NPC64305
0.6962	Remote Similarity	NPC472459
0.6923	Remote Similarity	NPC145038
0.6923	Remote Similarity	NPC56077
0.6923	Remote Similarity	NPC281131
0.6923	Remote Similarity	NPC253662
0.6923	Remote Similarity	NPC179950
0.6923	Remote Similarity	NPC88789
0.6923	Remote Similarity	NPC491374
0.6875	Remote Similarity	NPC175107
0.6824	Remote Similarity	NPC203259
0.6824	Remote Similarity	NPC33054
0.6824	Remote Similarity	NPC176740
0.6824	Remote Similarity	NPC471725
0.6824	Remote Similarity	NPC134532
0.6824	Remote Similarity	NPC602582
0.6795	Remote Similarity	NPC77672
0.6795	Remote Similarity	NPC133671
0.6795	Remote Similarity	NPC135391
0.6795	Remote Similarity	NPC78263
0.6795	Remote Similarity	NPC250069
0.675	Remote Similarity	NPC21100
0.6747	Remote Similarity	NPC116864
0.6747	Remote Similarity	NPC244776
0.6706	Remote Similarity	NPC173582
0.6706	Remote Similarity	NPC265885
0.6706	Remote Similarity	NPC181465
0.6706	Remote Similarity	NPC215710
0.6706	Remote Similarity	NPC473438
0.6706	Remote Similarity	NPC253788
0.6667	Remote Similarity	NPC191306
0.6628	Remote Similarity	NPC605592
0.6627	Remote Similarity	NPC203050
0.6627	Remote Similarity	NPC225434
0.6625	Remote Similarity	NPC305811
0.6582	Remote Similarity	NPC19388
0.6582	Remote Similarity	NPC240431
0.6582	Remote Similarity	NPC55786
0.6556	Remote Similarity	NPC476472
0.6556	Remote Similarity	NPC294815
0.6556	Remote Similarity	NPC16194
0.6548	Remote Similarity	NPC95866
0.6543	Remote Similarity	NPC325555
0.6543	Remote Similarity	NPC226304
0.6538	Remote Similarity	NPC67037
0.6538	Remote Similarity	NPC255615
0.6512	Remote Similarity	NPC39834
0.6477	Remote Similarity	NPC153755
0.6429	Remote Similarity	NPC476215
0.641	Remote Similarity	NPC288084
0.6395	Remote Similarity	NPC609888
0.6375	Remote Similarity	NPC249281
0.6375	Remote Similarity	NPC254306
0.6333	Remote Similarity	NPC606657
0.631	Remote Similarity	NPC209023
0.6289	Remote Similarity	NPC470718
0.6265	Remote Similarity	NPC159579
0.625	Remote Similarity	NPC155877
0.622	Remote Similarity	NPC46420
0.622	Remote Similarity	NPC52550
0.622	Remote Similarity	NPC271692
0.6203	Remote Similarity	NPC276222
0.6203	Remote Similarity	NPC274618
0.6203	Remote Similarity	NPC34531
0.6203	Remote Similarity	NPC118284
0.6203	Remote Similarity	NPC608147
0.6197	Remote Similarity	NPC82325
0.6196	Remote Similarity	NPC89127
0.6154	Remote Similarity	NPC122467
0.6145	Remote Similarity	NPC216496
0.6136	Remote Similarity	NPC471748
0.6136	Remote Similarity	NPC67326
0.6136	Remote Similarity	NPC163242
0.6136	Remote Similarity	NPC272068
0.6076	Remote Similarity	NPC54802
0.6076	Remote Similarity	NPC197304
0.6071	Remote Similarity	NPC182121
0.6071	Remote Similarity	NPC129217
0.6067	Remote Similarity	NPC156869
0.6044	Remote Similarity	NPC12013
0.6044	Remote Similarity	NPC11432
0.6044	Remote Similarity	NPC477613
0.6024	Remote Similarity	NPC27640
0.6023	Remote Similarity	NPC471079
0.6023	Remote Similarity	NPC29958
0.6023	Remote Similarity	NPC139320
0.6022	Remote Similarity	NPC220173
0.6	Remote Similarity	NPC129264
0.5979	Remote Similarity	NPC173837
0.5978	Remote Similarity	NPC37668
0.5974	Remote Similarity	NPC268668
0.5952	Remote Similarity	NPC59534
0.5938	Remote Similarity	NPC89052
0.593	Remote Similarity	NPC116458
0.593	Remote Similarity	NPC246943
0.593	Remote Similarity	NPC605784
0.5904	Remote Similarity	NPC158674
0.5895	Remote Similarity	NPC223426
0.5865	Remote Similarity	NPC192539
0.5862	Remote Similarity	NPC276377
0.5854	Remote Similarity	NPC476771
0.5851	Remote Similarity	NPC85751
0.5851	Remote Similarity	NPC471669
0.5851	Remote Similarity	NPC19240
0.5833	Remote Similarity	NPC81042
0.5806	Remote Similarity	NPC270448
0.5795	Remote Similarity	NPC254855
0.5795	Remote Similarity	NPC94610
0.5789	Remote Similarity	NPC221342
0.5789	Remote Similarity	NPC476470
0.5783	Remote Similarity	NPC476772
0.5761	Remote Similarity	NPC470125
0.573	Remote Similarity	NPC278419
0.573	Remote Similarity	NPC179198
0.5729	Remote Similarity	NPC602448
0.5728	Remote Similarity	NPC156785
0.5698	Remote Similarity	NPC235260
0.5698	Remote Similarity	NPC155763
0.5684	Remote Similarity	NPC76831
0.5682	Remote Similarity	NPC170052
0.5682	Remote Similarity	NPC66087
0.5682	Remote Similarity	NPC135846
0.567	Remote Similarity	NPC214621
0.567	Remote Similarity	NPC34267
0.5667	Remote Similarity	NPC187379
0.5657	Remote Similarity	NPC219043
0.5657	Remote Similarity	NPC292019
0.5657	Remote Similarity	NPC202908
0.5657	Remote Similarity	NPC477895
0.5652	Remote Similarity	NPC35167
0.5647	Remote Similarity	NPC349108
0.5638	Remote Similarity	NPC104883
0.5638	Remote Similarity	NPC488679
0.5632	Remote Similarity	NPC85707
0.5632	Remote Similarity	NPC21666
0.5632	Remote Similarity	NPC224530
0.5618	Remote Similarity	NPC265115
0.5612	Remote Similarity	NPC203145
0.56	Remote Similarity	NPC217520
0.56	Remote Similarity	NPC303694
0.5595	Remote Similarity	NPC289667
0.5595	Remote Similarity	NPC143851
0.5591	Remote Similarity	NPC126784
0.5591	Remote Similarity	NPC241423
0.5591	Remote Similarity	NPC154741
0.5581	Remote Similarity	NPC42773
0.5581	Remote Similarity	NPC45522
0.5577	Remote Similarity	NPC162394
0.5577	Remote Similarity	NPC474522
0.5556	Remote Similarity	NPC189564
0.5543	Remote Similarity	NPC150164
0.5532	Remote Similarity	NPC483414
0.5524	Remote Similarity	NPC480444
0.5517	Remote Similarity	NPC48093
0.5495	Remote Similarity	NPC258044
0.5495	Remote Similarity	NPC217387
0.549	Remote Similarity	NPC139571
0.5484	Remote Similarity	NPC473571
0.5484	Remote Similarity	NPC110941
0.5484	Remote Similarity	NPC186816
0.5481	Remote Similarity	NPC480445
0.5474	Remote Similarity	NPC72016
0.5472	Remote Similarity	NPC241781
0.5465	Remote Similarity	NPC488080
0.5465	Remote Similarity	NPC169977
0.5464	Remote Similarity	NPC470445
0.5455	Remote Similarity	NPC259957
0.5455	Remote Similarity	NPC189913
0.5455	Remote Similarity	NPC197285
0.5455	Remote Similarity	NPC601710
0.5446	Remote Similarity	NPC470712
0.5444	Remote Similarity	NPC4390
0.5444	Remote Similarity	NPC600989
0.5435	Remote Similarity	NPC196127
0.5435	Remote Similarity	NPC470405

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC17350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4645
0.1-0.2	4449
0.2-0.3	41
0.3-0.4	9
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.6824	Remote Similarity	NPD6797	Phase 2
0.5051	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