NPASS Compound

Natural Product: NPC255634

Natural Product ID	NPC255634
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KKPKUPKKMALLKG-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	56677686
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 76 80 0 0 0 0 0 0 0 0999 V2000 -5.5720 7.1001 -0.8707 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3161 6.5395 -0.5954 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0744 5.2086 -0.8561 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1009 4.4327 -1.3983 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8636 3.1000 -1.6602 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6424 2.5161 -1.4012 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6039 3.2637 -0.8626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8663 4.5985 -0.6083 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4479 2.7309 -0.6131 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1258 1.4604 -0.8301 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 1.0123 -0.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8076 -0.1512 -0.8711 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1013 -0.5043 -0.4647 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8417 0.3330 0.3376 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2839 1.5097 0.7237 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9960 1.8498 0.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0818 -0.0458 0.7054 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0306 0.6070 1.4980 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2456 0.8498 0.6425 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5142 0.3214 1.2106 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3788 -0.9870 1.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0414 -1.2081 2.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2991 -2.3718 1.9399 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1429 -3.5059 1.8749 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3008 -0.0723 2.6691 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6988 -2.0584 1.0704 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3912 0.0923 0.1248 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0841 0.3155 -0.6574 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0982 0.6669 -1.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3735 1.1936 -1.6463 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2663 0.4611 -2.1313 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9287 -0.6879 -1.6196 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4047 -1.5601 -0.5849 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5763 -2.7634 -0.4307 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1786 -3.6327 0.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6701 -3.6188 0.6507 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1814 -3.0905 -0.6684 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6754 -3.1433 -0.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2575 -2.2522 0.2018 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7207 -1.8659 -1.0018 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1654 -2.9196 1.7422 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7179 -4.9354 0.4164 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5288 -3.4725 -1.6357 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8925 2.3342 -2.2009 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8817 6.9241 -1.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5509 8.2165 -0.7064 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3638 6.7298 -0.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.8534 -1.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0689 5.2143 -0.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2889 -0.8211 -1.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4897 -1.4684 -0.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7853 2.2427 1.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5686 2.7941 0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6137 1.5884 1.8048 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3783 1.9423 0.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0043 1.1048 1.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1782 -0.9991 2.7040 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2322 -1.5467 3.6283 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0378 -2.1613 0.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4234 -2.6767 2.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6738 -4.1979 1.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6564 -2.1208 0.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1796 0.6852 -0.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1884 0.5431 -1.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5332 -0.9998 0.3490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5368 -2.5145 -0.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8220 -3.2441 1.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0343 -4.6622 0.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8267 -3.8262 -1.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0574 -2.8783 -1.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0714 -4.1730 -0.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7225 -1.5029 -0.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0389 -3.2641 2.0190 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9833 -5.2036 1.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 -4.1169 -1.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6031 1.8881 -1.6520 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 1 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 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 10 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 5 44 1 0 8 3 1 0 16 11 1 0 25 18 1 0 40 33 1 0 30 6 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 8 49 1 0 12 50 1 0 13 51 1 0 15 52 1 0 16 53 1 0 18 54 1 0 19 55 1 0 20 56 1 0 21 57 1 0 22 58 1 0 23 59 1 0 23 60 1 0 24 61 1 0 26 62 1 0 27 63 1 0 28 64 1 0 33 65 1 0 34 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 38 70 1 0 38 71 1 0 39 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	KKPKUPKKMALLKG-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-39-12-6-13(31)17-14(7-12)41-25(26(20(17)34)44-28-24(38)22(36)19(33)16(9-30)43-28)10-2-4-11(5-3-10)40-27-23(37)21(35)18(32)15(8-29)42-27/h2-7,15-16,18-19,21-24,27-33,35-38H,8-9H2,1H3
SMILES	COc1cc(c2c(c1)oc(c1ccc(cc1)OC1C(C(C(C(CO)O1)O)O)O)c(c2=O)OC1C(C(C(C(CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	-0.602 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.629 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.091 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	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:	0.126	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.618	Fsp³:	0.464
MCE-18:	118.585 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.162	Fluc inhibitor:	0.153 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.901 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.95 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.179	Promiscuous compounds:	0.326

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.542	MDCK Permeability:	-5.173
Pgp-inhibitor:	0.0	Pgp-substrate:	0.85
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):	1.0
20% Bioavailability (F20%):	0.445	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.754
Plasma Protein Binding (PPB):	75.714%	Volume Distribution (VD):	-0.179
Fu:	23.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.952	BCRP inhibitor:	0.576
BSEP inhibitor:	0.027

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.998	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.015
HLM stability:	0.006 ? 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):

1.451

Half-life (T1/2):

3.057

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.245
Human Hepatotoxicity (H-HT):	0.552	Drug-induced Liver Injury (DILI):	0.911
AMES Toxicity:	0.696	Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.144	Skin Sensitization:	0.035
Carcinogencity:	0.212	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.047	Ototoxicity:	0.99
Hematotoxicity:	0.04	Drug-induced Nephrotoxicity:	0.056
Genotoxicity:	0.169	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.046	Hek293 Cytotoxicity:	0.611
BCF:	0.501 ? 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:	3.141 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.146 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.921 ? 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
NPO16309	Semen astragali complanati	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16309	Semen astragali complanati	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20554	Astragalus complanatus	Species	Fabaceae	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 NPC255634 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	20848
0.1-0.2	24623
0.2-0.3	2933
0.3-0.4	846
0.4-0.5	343
0.5-0.6	101
0.6-0.7	79
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC289667
0.8194	Intermediate Similarity	NPC297987
0.7945	Intermediate Similarity	NPC136042
0.7838	Intermediate Similarity	NPC84362
0.7733	Intermediate Similarity	NPC472459
0.7703	Intermediate Similarity	NPC64305
0.7662	Intermediate Similarity	NPC116458
0.7662	Intermediate Similarity	NPC246943
0.7595	Intermediate Similarity	NPC251417
0.7436	Intermediate Similarity	NPC605784
0.7368	Intermediate Similarity	NPC46420
0.7333	Intermediate Similarity	NPC277532
0.7237	Intermediate Similarity	NPC95090
0.7237	Intermediate Similarity	NPC27408
0.7179	Intermediate Similarity	NPC611303
0.7143	Intermediate Similarity	NPC24043
0.7143	Intermediate Similarity	NPC64425
0.7143	Intermediate Similarity	NPC271692
0.7089	Intermediate Similarity	NPC486578
0.7013	Intermediate Similarity	NPC158674
0.6962	Remote Similarity	NPC488071
0.6883	Remote Similarity	NPC249281
0.6875	Remote Similarity	NPC22832
0.6875	Remote Similarity	NPC120099
0.6875	Remote Similarity	NPC21666
0.679	Remote Similarity	NPC607707
0.675	Remote Similarity	NPC285197
0.6737	Remote Similarity	NPC295625
0.6709	Remote Similarity	NPC73511
0.6702	Remote Similarity	NPC470716
0.6667	Remote Similarity	NPC148710
0.6667	Remote Similarity	NPC243930
0.6667	Remote Similarity	NPC77672
0.6667	Remote Similarity	NPC133671
0.6667	Remote Similarity	NPC135391
0.6667	Remote Similarity	NPC470715
0.6667	Remote Similarity	NPC78263
0.6667	Remote Similarity	NPC250069
0.6591	Remote Similarity	NPC35119
0.6582	Remote Similarity	NPC277205
0.6582	Remote Similarity	NPC37919
0.6552	Remote Similarity	NPC240306
0.6543	Remote Similarity	NPC60735
0.6543	Remote Similarity	NPC26230
0.6506	Remote Similarity	NPC488072
0.65	Remote Similarity	NPC488080
0.65	Remote Similarity	NPC169977
0.6463	Remote Similarity	NPC609478
0.6456	Remote Similarity	NPC58053
0.642	Remote Similarity	NPC42773
0.642	Remote Similarity	NPC45522
0.642	Remote Similarity	NPC325555
0.642	Remote Similarity	NPC226304
0.6404	Remote Similarity	NPC32641
0.6404	Remote Similarity	NPC256188
0.6375	Remote Similarity	NPC145038
0.6375	Remote Similarity	NPC56077
0.6375	Remote Similarity	NPC281131
0.6375	Remote Similarity	NPC253662
0.6375	Remote Similarity	NPC179950
0.6375	Remote Similarity	NPC323593
0.6375	Remote Similarity	NPC88789
0.6375	Remote Similarity	NPC203500
0.6375	Remote Similarity	NPC189142
0.6375	Remote Similarity	NPC77660
0.6375	Remote Similarity	NPC491374
0.6364	Remote Similarity	NPC470720
0.6333	Remote Similarity	NPC5319
0.6324	Remote Similarity	NPC262094
0.6316	Remote Similarity	NPC25523
0.6316	Remote Similarity	NPC164704
0.631	Remote Similarity	NPC203050
0.631	Remote Similarity	NPC225434
0.631	Remote Similarity	NPC276377
0.631	Remote Similarity	NPC601586
0.6296	Remote Similarity	NPC186807
0.6296	Remote Similarity	NPC603655
0.6263	Remote Similarity	NPC470717
0.625	Remote Similarity	NPC19388
0.625	Remote Similarity	NPC261866
0.625	Remote Similarity	NPC240431
0.625	Remote Similarity	NPC39360
0.625	Remote Similarity	NPC55786
0.625	Remote Similarity	NPC29763
0.625	Remote Similarity	NPC210003
0.6237	Remote Similarity	NPC14187
0.6222	Remote Similarity	NPC606657
0.622	Remote Similarity	NPC599850
0.619	Remote Similarity	NPC311830
0.617	Remote Similarity	NPC121703
0.6154	Remote Similarity	NPC486577
0.6146	Remote Similarity	NPC480441
0.6136	Remote Similarity	NPC150164
0.61	Remote Similarity	NPC470719
0.6092	Remote Similarity	NPC480466
0.6087	Remote Similarity	NPC76831
0.6071	Remote Similarity	NPC101026
0.6071	Remote Similarity	NPC488077
0.6067	Remote Similarity	NPC186816
0.5977	Remote Similarity	NPC480463
0.5976	Remote Similarity	NPC8573
0.5976	Remote Similarity	NPC234739
0.5957	Remote Similarity	NPC135358
0.5952	Remote Similarity	NPC307938
0.5904	Remote Similarity	NPC22195
0.5904	Remote Similarity	NPC27640
0.5904	Remote Similarity	NPC181712
0.5904	Remote Similarity	NPC21190
0.5882	Remote Similarity	NPC601144
0.5882	Remote Similarity	NPC605067
0.5875	Remote Similarity	NPC288084
0.587	Remote Similarity	NPC72016
0.5854	Remote Similarity	NPC143851
0.5833	Remote Similarity	NPC117260
0.5795	Remote Similarity	NPC473682
0.5765	Remote Similarity	NPC168584
0.5765	Remote Similarity	NPC219904
0.5765	Remote Similarity	NPC609451
0.5686	Remote Similarity	NPC470713
0.5657	Remote Similarity	NPC470712
0.5652	Remote Similarity	NPC488073
0.5647	Remote Similarity	NPC201292
0.5638	Remote Similarity	NPC142142
0.5634	Remote Similarity	NPC103904
0.5632	Remote Similarity	NPC206123
0.5616	Remote Similarity	NPC270620
0.561	Remote Similarity	NPC67037
0.561	Remote Similarity	NPC255615
0.5604	Remote Similarity	NPC156869
0.5595	Remote Similarity	NPC197896
0.5595	Remote Similarity	NPC313163
0.557	Remote Similarity	NPC191154
0.5556	Remote Similarity	NPC146679
0.5556	Remote Similarity	NPC139320
0.5543	Remote Similarity	NPC131745
0.5542	Remote Similarity	NPC111929
0.5542	Remote Similarity	NPC320283
0.5542	Remote Similarity	NPC41121
0.5541	Remote Similarity	NPC236769
0.5529	Remote Similarity	NPC105025
0.5529	Remote Similarity	NPC45638
0.5524	Remote Similarity	NPC138990
0.55	Remote Similarity	NPC134819
0.5495	Remote Similarity	NPC275454
0.5488	Remote Similarity	NPC34531
0.5484	Remote Similarity	NPC46202
0.5476	Remote Similarity	NPC238376
0.5465	Remote Similarity	NPC59534
0.5465	Remote Similarity	NPC21100
0.5465	Remote Similarity	NPC60966
0.5444	Remote Similarity	NPC278419
0.5444	Remote Similarity	NPC179198
0.5435	Remote Similarity	NPC22062
0.5435	Remote Similarity	NPC473634
0.5435	Remote Similarity	NPC138811
0.5429	Remote Similarity	NPC488078
0.5426	Remote Similarity	NPC483414
0.5417	Remote Similarity	NPC475382
0.5412	Remote Similarity	NPC93337
0.5412	Remote Similarity	NPC168822
0.5412	Remote Similarity	NPC265530
0.5405	Remote Similarity	NPC153758
0.5402	Remote Similarity	NPC175107
0.5402	Remote Similarity	NPC479402
0.5402	Remote Similarity	NPC80140
0.54	Remote Similarity	NPC48984
0.5393	Remote Similarity	NPC170052
0.5393	Remote Similarity	NPC135846
0.5393	Remote Similarity	NPC267254
0.5385	Remote Similarity	NPC29958
0.5368	Remote Similarity	NPC124155
0.5349	Remote Similarity	NPC245014
0.5349	Remote Similarity	NPC305811
0.5349	Remote Similarity	NPC349108
0.5349	Remote Similarity	NPC610763
0.5342	Remote Similarity	NPC188871
0.5341	Remote Similarity	NPC80188
0.5333	Remote Similarity	NPC265115
0.5327	Remote Similarity	NPC175429
0.5326	Remote Similarity	NPC267680
0.5326	Remote Similarity	NPC471748
0.5294	Remote Similarity	NPC127546
0.5294	Remote Similarity	NPC57625
0.5294	Remote Similarity	NPC44558
0.5294	Remote Similarity	NPC108831
0.5294	Remote Similarity	NPC19709
0.5294	Remote Similarity	NPC173637
0.5294	Remote Similarity	NPC317489
0.5294	Remote Similarity	NPC223424
0.5294	Remote Similarity	NPC182634
0.5294	Remote Similarity	NPC600591
0.5287	Remote Similarity	NPC182045
0.5287	Remote Similarity	NPC27942
0.5283	Remote Similarity	NPC488079
0.5281	Remote Similarity	NPC223747
0.5281	Remote Similarity	NPC88023
0.5281	Remote Similarity	NPC220169
0.5281	Remote Similarity	NPC309025
0.5281	Remote Similarity	NPC602805
0.5275	Remote Similarity	NPC8856

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC255634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4996
0.1-0.2	4050
0.2-0.3	88
0.3-0.4	8
0.4-0.5	4
0.5-0.6	3
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
0.6333	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7808	Phase 3
0.5745	Remote Similarity	NPD7251	Phase 2
0.5208	Remote Similarity	NPD7054	Phase 4

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