NPASS Compound

Natural Product: NPC282176

Natural Product ID	NPC282176
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PUOSBMABMJBMGX-ZLEZCFKXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5495544
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 76 80 0 0 0 0 0 0 0 0999 V2000 5.0775 3.7076 1.5367 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6313 2.7741 0.4398 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8979 2.1617 0.9774 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3807 1.0869 0.0378 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4239 1.0547 -1.1310 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0473 0.7344 -0.5491 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1178 0.4471 -1.4121 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3390 -0.5427 -1.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2749 -1.0461 -0.7225 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8639 -1.4842 0.5613 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0785 -2.5231 1.3295 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2232 -3.4032 0.4839 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5525 -2.4846 -0.5460 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4199 -3.1720 -1.2501 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7407 -2.8336 -1.2905 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6221 -3.6202 -2.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9558 -3.2815 -2.1068 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4546 -2.1978 -1.4171 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6185 -1.4148 -0.6559 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2655 -1.7709 -0.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0472 -0.3790 0.0150 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3097 0.0355 0.0442 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6375 1.2045 0.8388 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5683 1.9428 1.3606 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7576 3.0510 2.1569 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0345 3.4769 2.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0999 2.7675 1.9711 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8705 1.6601 1.1757 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3815 3.1978 2.2891 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2214 4.5943 3.2736 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1818 -0.7094 -0.7005 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7785 -1.8339 -1.4409 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5772 -2.5034 -2.1111 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5312 -0.3775 -0.7659 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8867 0.4723 -1.8550 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8264 -4.0608 -2.8727 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5984 -2.1093 -1.3990 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2725 -4.0067 1.2751 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0014 -3.3416 1.9931 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8959 -0.3252 1.3931 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6559 1.8505 0.2144 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8376 -0.0003 -1.9531 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3350 -0.1779 0.6589 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9209 3.1024 1.0918 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2084 3.2123 2.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6176 4.6750 1.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0044 3.8393 1.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8225 3.4806 -0.4158 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6776 1.7295 1.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4197 1.2908 -0.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4789 2.0249 -1.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2571 -0.0636 0.1864 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -1.5013 -2.0404 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7215 -0.2735 -2.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4790 -0.2639 -0.6053 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8522 -1.8988 0.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3980 -2.0409 2.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8282 -4.1532 -0.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2052 -1.5890 -0.0129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1761 -4.4525 -2.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6559 -1.1149 -0.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5426 1.6585 1.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9035 3.5853 2.5340 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7359 1.1380 0.8383 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5387 4.1928 2.3236 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6120 5.4381 2.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1804 1.3199 -1.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8940 0.9091 -1.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8005 -0.1202 -2.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5465 -4.1690 -3.8533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6246 -3.6866 1.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0523 -4.2345 1.5790 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6249 -0.5006 2.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1875 -0.7180 -2.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2642 -0.3865 0.9172 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6426 2.9504 0.4347 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 7 8 1 0 8 9 1 0 9 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 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 26 30 1 0 22 31 2 0 31 32 1 0 32 33 2 0 31 34 1 0 34 35 1 0 17 36 1 0 13 37 1 0 12 38 1 0 11 39 1 0 10 40 1 0 6 41 1 0 5 42 1 0 4 43 1 0 3 44 1 0 41 2 1 0 37 9 1 0 20 15 1 0 28 23 1 0 32 18 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 6 3 49 1 1 4 50 1 6 5 51 1 6 6 52 1 1 8 53 1 0 8 54 1 0 9 55 1 1 10 56 1 6 11 57 1 1 12 58 1 6 13 59 1 1 16 60 1 0 20 61 1 0 24 62 1 0 25 63 1 0 28 64 1 0 29 65 1 0 30 66 1 0 35 67 1 0 35 68 1 0 35 69 1 0 36 70 1 0 38 71 1 0 39 72 1 0 40 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	PUOSBMABMJBMGX-ZLEZCFKXSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(44-16)42-11-6-14(31)17-15(7-11)43-25(26(39-2)20(17)34)10-3-4-12(29)13(30)5-10/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27+,28+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc(c4c(c3)oc(c3ccc(c(c3)O)O)c(c4=O)OC)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.485 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.035 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.547 ? 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:	0.137	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.778	Fsp³:	0.464
MCE-18:	122.073 ? 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:	1
Colloidal aggregators:	0.608	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.914 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.659 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.076	Promiscuous compounds:	0.526

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.349	MDCK Permeability:	-5.319
Pgp-inhibitor:	0.0	Pgp-substrate:	0.644
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):	0.859
20% Bioavailability (F20%):	0.242	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.352
Plasma Protein Binding (PPB):	80.92%	Volume Distribution (VD):	-0.158
Fu:	17.4% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.955
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.274
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.012
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.588
HLM stability:	0.084 ? 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):

1.901

Half-life (T1/2):

4.904

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.206
Human Hepatotoxicity (H-HT):	0.273	Drug-induced Liver Injury (DILI):	0.947
AMES Toxicity:	0.862	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.014	Skin Sensitization:	0.988
Carcinogencity:	0.031	Eye Corrosion:	0.0
Eye Irritation:	0.121	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.978
Hematotoxicity:	0.045	Drug-induced Nephrotoxicity:	0.205
Genotoxicity:	0.661	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.55	Hek293 Cytotoxicity:	0.233
BCF:	0.482 ? 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:	3.098 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.652 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.782 ? 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
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	whole plant	Gongshan County, Yunnan, China	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21261296]
NPO19496	Bidens leucantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090869]
NPO19496	Bidens leucantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19496	Bidens leucantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	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 NPC282176 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	20045
0.1-0.2	25749
0.2-0.3	3037
0.3-0.4	508
0.4-0.5	275
0.5-0.6	112
0.6-0.7	63
0.7-0.8	2
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC186816
0.8095	Intermediate Similarity	NPC67105
0.8	Intermediate Similarity	NPC210073
0.7931	Intermediate Similarity	NPC470443
0.7875	Intermediate Similarity	NPC271692
0.766	Intermediate Similarity	NPC480441
0.7614	Intermediate Similarity	NPC126784
0.7614	Intermediate Similarity	NPC241423
0.7586	Intermediate Similarity	NPC203259
0.7586	Intermediate Similarity	NPC33054
0.7586	Intermediate Similarity	NPC176740
0.7586	Intermediate Similarity	NPC471725
0.7586	Intermediate Similarity	NPC134532
0.7586	Intermediate Similarity	NPC602582
0.7283	Intermediate Similarity	NPC473073
0.7273	Intermediate Similarity	NPC44931
0.7273	Intermediate Similarity	NPC227508
0.7229	Intermediate Similarity	NPC84362
0.7191	Intermediate Similarity	NPC22062
0.7191	Intermediate Similarity	NPC473634
0.7191	Intermediate Similarity	NPC138811
0.7174	Intermediate Similarity	NPC142142
0.7093	Intermediate Similarity	NPC605784
0.7065	Intermediate Similarity	NPC209296
0.7024	Intermediate Similarity	NPC46420
0.6939	Remote Similarity	NPC25523
0.6905	Remote Similarity	NPC158674
0.6889	Remote Similarity	NPC173582
0.6889	Remote Similarity	NPC265885
0.6889	Remote Similarity	NPC181465
0.6889	Remote Similarity	NPC215710
0.6889	Remote Similarity	NPC473438
0.6889	Remote Similarity	NPC253788
0.6875	Remote Similarity	NPC14187
0.6809	Remote Similarity	NPC486577
0.6786	Remote Similarity	NPC249281
0.6739	Remote Similarity	NPC473571
0.6739	Remote Similarity	NPC110941
0.6737	Remote Similarity	NPC476472
0.6737	Remote Similarity	NPC294815
0.6737	Remote Similarity	NPC16194
0.6706	Remote Similarity	NPC136042
0.6703	Remote Similarity	NPC39834
0.6702	Remote Similarity	NPC473327
0.6667	Remote Similarity	NPC488073
0.6667	Remote Similarity	NPC611303
0.663	Remote Similarity	NPC65563
0.663	Remote Similarity	NPC470949
0.663	Remote Similarity	NPC156869
0.6629	Remote Similarity	NPC276377
0.6588	Remote Similarity	NPC238376
0.6522	Remote Similarity	NPC67326
0.6489	Remote Similarity	NPC488074
0.6437	Remote Similarity	NPC27640
0.6421	Remote Similarity	NPC65711
0.6395	Remote Similarity	NPC19709
0.6354	Remote Similarity	NPC122467
0.6344	Remote Similarity	NPC275454
0.6333	Remote Similarity	NPC116458
0.6333	Remote Similarity	NPC246943
0.6277	Remote Similarity	NPC303913
0.6277	Remote Similarity	NPC150164
0.6263	Remote Similarity	NPC470446
0.6224	Remote Similarity	NPC89127
0.6196	Remote Similarity	NPC116864
0.6196	Remote Similarity	NPC244776
0.6186	Remote Similarity	NPC32641
0.6186	Remote Similarity	NPC256188
0.618	Remote Similarity	NPC59534
0.6176	Remote Similarity	NPC292019
0.6176	Remote Similarity	NPC202908
0.6162	Remote Similarity	NPC470445
0.6146	Remote Similarity	NPC240306
0.6139	Remote Similarity	NPC121703
0.6067	Remote Similarity	NPC305811
0.6042	Remote Similarity	NPC204693
0.6023	Remote Similarity	NPC127546
0.6023	Remote Similarity	NPC57625
0.6023	Remote Similarity	NPC173637
0.6023	Remote Similarity	NPC317489
0.6023	Remote Similarity	NPC223424
0.6023	Remote Similarity	NPC600591
0.6022	Remote Similarity	NPC265115
0.602	Remote Similarity	NPC473623
0.602	Remote Similarity	NPC72016
0.602	Remote Similarity	NPC35119
0.602	Remote Similarity	NPC606657
0.6	Remote Similarity	NPC101636
0.5974	Remote Similarity	NPC188871
0.596	Remote Similarity	NPC488089
0.5957	Remote Similarity	NPC251417
0.5955	Remote Similarity	NPC297987
0.5895	Remote Similarity	NPC471079
0.5859	Remote Similarity	NPC229409
0.5843	Remote Similarity	NPC108831
0.5843	Remote Similarity	NPC182634
0.5825	Remote Similarity	NPC11468
0.581	Remote Similarity	NPC303694
0.5784	Remote Similarity	NPC135358
0.5778	Remote Similarity	NPC277205
0.5778	Remote Similarity	NPC37919
0.5758	Remote Similarity	NPC12013
0.5758	Remote Similarity	NPC483414
0.5758	Remote Similarity	NPC11432
0.5758	Remote Similarity	NPC483415
0.5758	Remote Similarity	NPC477613
0.5745	Remote Similarity	NPC190003
0.573	Remote Similarity	NPC473043
0.573	Remote Similarity	NPC331652
0.5729	Remote Similarity	NPC480466
0.5729	Remote Similarity	NPC187379
0.57	Remote Similarity	NPC483416
0.5676	Remote Similarity	NPC209550
0.5673	Remote Similarity	NPC89052
0.5667	Remote Similarity	NPC289667
0.5657	Remote Similarity	NPC475366
0.5625	Remote Similarity	NPC254540
0.5619	Remote Similarity	NPC470451
0.5619	Remote Similarity	NPC189564
0.5612	Remote Similarity	NPC605592
0.5607	Remote Similarity	NPC277532
0.5604	Remote Similarity	NPC189142
0.5604	Remote Similarity	NPC77660
0.5591	Remote Similarity	NPC488071
0.5588	Remote Similarity	NPC471669
0.5566	Remote Similarity	NPC173837
0.5556	Remote Similarity	NPC115674
0.5536	Remote Similarity	NPC241781
0.5534	Remote Similarity	NPC298171
0.5534	Remote Similarity	NPC470449
0.5534	Remote Similarity	NPC221342
0.5534	Remote Similarity	NPC476470
0.5524	Remote Similarity	NPC203145
0.5521	Remote Similarity	NPC95866
0.5514	Remote Similarity	NPC473644
0.55	Remote Similarity	NPC64425
0.55	Remote Similarity	NPC153755
0.5495	Remote Similarity	NPC162394
0.5481	Remote Similarity	NPC602448
0.5474	Remote Similarity	NPC99957
0.5463	Remote Similarity	NPC311850
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC233994
0.5455	Remote Similarity	NPC479405
0.5437	Remote Similarity	NPC470447
0.5426	Remote Similarity	NPC175107
0.5405	Remote Similarity	NPC198199
0.54	Remote Similarity	NPC479404
0.5392	Remote Similarity	NPC37668
0.5385	Remote Similarity	NPC111929
0.5385	Remote Similarity	NPC320283
0.5385	Remote Similarity	NPC41121
0.5376	Remote Similarity	NPC349108
0.5357	Remote Similarity	NPC156785
0.5347	Remote Similarity	NPC46202
0.5347	Remote Similarity	NPC64051
0.5333	Remote Similarity	NPC223426
0.5319	Remote Similarity	NPC42773
0.5319	Remote Similarity	NPC45522
0.5319	Remote Similarity	NPC599850
0.5315	Remote Similarity	NPC68592
0.5312	Remote Similarity	NPC223747
0.53	Remote Similarity	NPC129827
0.53	Remote Similarity	NPC155877
0.5294	Remote Similarity	NPC211532
0.5294	Remote Similarity	NPC479403
0.5294	Remote Similarity	NPC488364
0.5283	Remote Similarity	NPC81042
0.528	Remote Similarity	NPC482520
0.528	Remote Similarity	NPC482519
0.5269	Remote Similarity	NPC145038
0.5269	Remote Similarity	NPC56077
0.5269	Remote Similarity	NPC281131
0.5269	Remote Similarity	NPC253662
0.5269	Remote Similarity	NPC179950
0.5269	Remote Similarity	NPC88789
0.5269	Remote Similarity	NPC491374
0.5268	Remote Similarity	NPC298666
0.5263	Remote Similarity	NPC120952
0.5263	Remote Similarity	NPC138990
0.5263	Remote Similarity	NPC219904
0.5258	Remote Similarity	NPC355481
0.5253	Remote Similarity	NPC609888
0.5217	Remote Similarity	NPC192539
0.5217	Remote Similarity	NPC135599
0.5217	Remote Similarity	NPC73855
0.5217	Remote Similarity	NPC175429
0.5217	Remote Similarity	NPC113968
0.5217	Remote Similarity	NPC328940
0.5217	Remote Similarity	NPC277174
0.5217	Remote Similarity	NPC606877
0.5208	Remote Similarity	NPC181616
0.5192	Remote Similarity	NPC270675
0.5192	Remote Similarity	NPC195685
0.5185	Remote Similarity	NPC146679
0.5175	Remote Similarity	NPC488078
0.5169	Remote Similarity	NPC487499
0.5158	Remote Similarity	NPC27942
0.5149	Remote Similarity	NPC475155
0.5143	Remote Similarity	NPC80068

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC282176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5273
0.1-0.2	3820
0.2-0.3	48
0.3-0.4	2
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8488	Intermediate Similarity	NPD7251	Phase 2
0.7586	Intermediate Similarity	NPD6797	Phase 2
0.7065	Intermediate Similarity	NPD7054	Phase 4
0.6979	Remote Similarity	NPD7808	Phase 3
0.5524	Remote Similarity	NPD7472	Pre-clinical

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