NPASS Compound

Natural Product: NPC171754

Natural Product ID	NPC171754
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QZXHFNCQMMUANB-PGKIHVCZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44259248
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 74 78 0 0 0 0 0 0 0 0999 V2000 1.9024 0.0542 0.0347 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1782 0.3366 -0.3911 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2983 -0.1627 0.2939 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0356 -0.9312 1.3888 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7206 -1.2119 1.8132 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6329 -0.7338 1.1573 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2480 -0.9761 1.5271 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1758 -1.7262 2.5876 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5323 -1.9159 2.8823 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8930 -2.6106 3.8635 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4467 -1.3092 2.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7916 -1.4425 2.2662 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6737 -0.8125 1.4014 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2826 -0.0513 0.3264 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8926 0.0572 0.1451 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9914 -0.5579 0.9883 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7041 -0.4351 0.7890 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1157 0.5937 -0.5608 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4946 0.5692 -0.5069 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0126 1.9583 -0.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1734 2.3446 -1.1449 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0404 1.1170 -1.2771 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2735 -0.0019 -1.9064 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8895 -1.3119 -1.4544 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7032 -1.5175 -0.0992 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9467 -0.0391 -1.6458 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5098 0.7239 -0.0481 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7757 2.8282 -2.3877 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0159 2.9335 -0.4902 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2628 -2.1954 3.3314 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7266 -2.3337 3.4196 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0698 -1.4587 2.1158 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5107 0.1740 -0.2077 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8014 -0.0965 0.1466 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4107 -0.9381 -0.9918 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9090 -0.7567 -1.0630 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1644 0.6888 -1.4689 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9785 1.5060 -1.0010 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3799 2.9758 -0.8246 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7664 3.5131 -2.0699 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6164 1.0419 0.2379 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3323 1.0763 -0.7736 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3647 -1.6477 -2.0353 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0436 -2.2767 -0.8593 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0428 0.4416 -0.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3658 0.9555 -1.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6108 -1.8226 2.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7424 -0.9330 1.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5389 0.6467 -0.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8374 -0.0409 0.3402 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3242 2.0871 0.7740 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7796 3.1119 -0.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9054 1.3882 -1.9168 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4270 0.0565 -3.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9306 -1.4383 -1.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2846 -2.1144 -1.9699 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0266 -2.4318 0.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3236 0.1513 -0.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1006 2.2794 -3.1404 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4671 3.7968 -0.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5371 -3.1712 3.2564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6741 -3.2988 3.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9807 -1.4318 3.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8905 -0.7255 1.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9884 -0.5861 -1.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3566 -0.9715 -0.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3425 0.7905 -2.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1916 1.4251 -1.7632 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2302 3.0149 -0.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4653 3.5037 -0.4495 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4389 4.4644 -2.1314 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1210 1.0520 -1.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6034 -2.5258 -1.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4296 -2.7153 -0.0801 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 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 24 25 1 0 23 26 1 0 22 27 1 0 21 28 1 0 20 29 1 0 12 30 1 0 8 31 1 0 4 32 1 0 3 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 39 40 1 0 38 41 1 0 37 42 1 0 36 43 1 0 35 44 1 0 6 1 1 0 17 7 1 0 26 19 1 0 41 34 1 0 16 11 1 0 1 45 1 0 2 46 1 0 5 47 1 0 13 48 1 0 15 49 1 0 19 50 1 1 20 51 1 0 21 52 1 1 22 53 1 6 23 54 1 0 24 55 1 0 24 56 1 0 25 57 1 0 27 58 1 0 28 59 1 0 29 60 1 0 30 61 1 0 31 62 1 0 32 63 1 0 34 64 1 1 35 65 1 0 36 66 1 1 37 67 1 6 38 68 1 0 39 69 1 0 39 70 1 0 40 71 1 0 42 72 1 0 43 73 1 0 44 74 1 0 M END

Standard InCHIKey	QZXHFNCQMMUANB-PGKIHVCZSA-N
Standard InCHI	InChI=1S/C27H30O17/c28-6-14-17(32)20(35)23(38)26(43-14)40-9-4-11(31)16-13(5-9)41-25(22(37)19(16)34)8-1-2-12(10(30)3-8)42-27-24(39)21(36)18(33)15(7-29)44-27/h1-5,14-15,17-18,20-21,23-24,26-33,35-39H,6-7H2/t14?,15?,17-,18-,20+,21+,23?,24?,26-,27-/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O)O)O)O)O[C@H]1C([C@H]([C@@H](C(CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	626.15	Volume:	561.108 ? Van der Waals volume.
Dense:	1.116	LogP:	-1.564 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.165 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.083 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	289.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.124	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.782	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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.691	Fluc inhibitor:	0.272 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.932 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.66 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.339	Promiscuous compounds:	0.47

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.701	MDCK Permeability:	-4.909
Pgp-inhibitor:	0.0	Pgp-substrate:	0.894
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%):	0.827	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.368
Plasma Protein Binding (PPB):	79.241%	Volume Distribution (VD):	-0.218
Fu:	23.209% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.953
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.31
BSEP inhibitor:	0.0

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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.208
HLM stability:	0.001 ? 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):

1.869

Half-life (T1/2):

5.119

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.09
Human Hepatotoxicity (H-HT):	0.556	Drug-induced Liver Injury (DILI):	0.931
AMES Toxicity:	0.727	Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	0.9
Carcinogencity:	0.083	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.99
Hematotoxicity:	0.078	Drug-induced Nephrotoxicity:	0.357
Genotoxicity:	0.36	RPMI-8226 Immunitoxicity:	0.14
A549 Cytotoxicity:	0.133	Hek293 Cytotoxicity:	0.241
BCF:	0.297 ? 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:	2.516 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.324 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.302 ? 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
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16748484]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20597533]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23656415]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23230	Allium cepa	Species	Amaryllidaceae	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 NPC171754 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	20857
0.1-0.2	25061
0.2-0.3	2651
0.3-0.4	868
0.4-0.5	252
0.5-0.6	95
0.6-0.7	37
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC285197
0.9571	High Similarity	NPC486578
0.8219	Intermediate Similarity	NPC277205
0.8219	Intermediate Similarity	NPC37919
0.8	Intermediate Similarity	NPC21100
0.7973	Intermediate Similarity	NPC323593
0.7973	Intermediate Similarity	NPC203500
0.7821	Intermediate Similarity	NPC601586
0.7407	Intermediate Similarity	NPC251417
0.7342	Intermediate Similarity	NPC22832
0.7215	Intermediate Similarity	NPC307938
0.7143	Intermediate Similarity	NPC254306
0.6923	Remote Similarity	NPC289667
0.6923	Remote Similarity	NPC238376
0.6824	Remote Similarity	NPC275454
0.675	Remote Similarity	NPC245014
0.6709	Remote Similarity	NPC108831
0.6709	Remote Similarity	NPC182634
0.6625	Remote Similarity	NPC95090
0.6625	Remote Similarity	NPC27408
0.6543	Remote Similarity	NPC84265
0.6506	Remote Similarity	NPC243930
0.6506	Remote Similarity	NPC197285
0.6506	Remote Similarity	NPC601144
0.6429	Remote Similarity	NPC607707
0.642	Remote Similarity	NPC297987
0.642	Remote Similarity	NPC136042
0.642	Remote Similarity	NPC189142
0.642	Remote Similarity	NPC77660
0.6386	Remote Similarity	NPC191306
0.6386	Remote Similarity	NPC60735
0.6386	Remote Similarity	NPC26230
0.6344	Remote Similarity	NPC135358
0.6341	Remote Similarity	NPC84362
0.6338	Remote Similarity	NPC200740
0.631	Remote Similarity	NPC605067
0.631	Remote Similarity	NPC609478
0.6296	Remote Similarity	NPC261866
0.6296	Remote Similarity	NPC39360
0.6296	Remote Similarity	NPC29763
0.6296	Remote Similarity	NPC210003
0.6265	Remote Similarity	NPC117260
0.6235	Remote Similarity	NPC311830
0.619	Remote Similarity	NPC611303
0.6067	Remote Similarity	NPC67105
0.6047	Remote Similarity	NPC116458
0.6047	Remote Similarity	NPC246943
0.6047	Remote Similarity	NPC605784
0.6024	Remote Similarity	NPC282987
0.593	Remote Similarity	NPC120099
0.593	Remote Similarity	NPC21666
0.5889	Remote Similarity	NPC227508
0.587	Remote Similarity	NPC64425
0.5833	Remote Similarity	NPC234739
0.5833	Remote Similarity	NPC609879
0.5825	Remote Similarity	NPC470719
0.5789	Remote Similarity	NPC80068
0.5765	Remote Similarity	NPC73511
0.5761	Remote Similarity	NPC131745
0.5682	Remote Similarity	NPC136761
0.5647	Remote Similarity	NPC197896
0.5647	Remote Similarity	NPC64305
0.5647	Remote Similarity	NPC313163
0.5625	Remote Similarity	NPC191154
0.56	Remote Similarity	NPC480796
0.5579	Remote Similarity	NPC209296
0.5568	Remote Similarity	NPC284960
0.5556	Remote Similarity	NPC134819
0.5529	Remote Similarity	NPC58053
0.5529	Remote Similarity	NPC143851
0.5517	Remote Similarity	NPC472459
0.5495	Remote Similarity	NPC8856
0.5464	Remote Similarity	NPC256760
0.5455	Remote Similarity	NPC80140
0.5429	Remote Similarity	NPC198199
0.5417	Remote Similarity	NPC35119
0.5417	Remote Similarity	NPC606657
0.5408	Remote Similarity	NPC287889
0.5402	Remote Similarity	NPC22195
0.5402	Remote Similarity	NPC186807
0.5402	Remote Similarity	NPC58716
0.5402	Remote Similarity	NPC181712
0.5402	Remote Similarity	NPC21190
0.5392	Remote Similarity	NPC480441
0.5392	Remote Similarity	NPC470715
0.5392	Remote Similarity	NPC25523
0.5392	Remote Similarity	NPC164704
0.5349	Remote Similarity	NPC249281
0.5349	Remote Similarity	NPC45618
0.5349	Remote Similarity	NPC476405
0.5349	Remote Similarity	NPC19709
0.5333	Remote Similarity	NPC295625
0.5327	Remote Similarity	NPC470720
0.5319	Remote Similarity	NPC183672
0.53	Remote Similarity	NPC14187
0.5288	Remote Similarity	NPC470716
0.5288	Remote Similarity	NPC255799
0.5287	Remote Similarity	NPC168822
0.5287	Remote Similarity	NPC146792
0.5281	Remote Similarity	NPC609451
0.5278	Remote Similarity	NPC120952
0.5263	Remote Similarity	NPC166753
0.5258	Remote Similarity	NPC32641
0.5258	Remote Similarity	NPC256188
0.5234	Remote Similarity	NPC470717
0.5233	Remote Similarity	NPC473043
0.5233	Remote Similarity	NPC331652
0.5227	Remote Similarity	NPC46420
0.5227	Remote Similarity	NPC271692
0.5222	Remote Similarity	NPC229729
0.5222	Remote Similarity	NPC601710
0.5217	Remote Similarity	NPC477848
0.52	Remote Similarity	NPC87125
0.5192	Remote Similarity	NPC277532
0.5181	Remote Similarity	NPC473241
0.5172	Remote Similarity	NPC77672
0.5172	Remote Similarity	NPC133671
0.5172	Remote Similarity	NPC135391
0.5172	Remote Similarity	NPC78263
0.5172	Remote Similarity	NPC250069
0.5169	Remote Similarity	NPC27942
0.5169	Remote Similarity	NPC60966
0.5165	Remote Similarity	NPC88023
0.5165	Remote Similarity	NPC309025
0.5128	Remote Similarity	NPC252933
0.5114	Remote Similarity	NPC145038
0.5114	Remote Similarity	NPC56077
0.5114	Remote Similarity	NPC281131
0.5114	Remote Similarity	NPC253662
0.5114	Remote Similarity	NPC179950
0.5114	Remote Similarity	NPC158674
0.5114	Remote Similarity	NPC88789
0.5114	Remote Similarity	NPC491374
0.5109	Remote Similarity	NPC203050
0.5109	Remote Similarity	NPC469931
0.5109	Remote Similarity	NPC225434
0.5109	Remote Similarity	NPC190003
0.5106	Remote Similarity	NPC187379
0.5104	Remote Similarity	NPC115674
0.5104	Remote Similarity	NPC169733
0.5102	Remote Similarity	NPC139060
0.5067	Remote Similarity	NPC152042
0.5056	Remote Similarity	NPC45638
0.5055	Remote Similarity	NPC80188

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC171754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5188
0.1-0.2	3874
0.2-0.3	71
0.3-0.4	10
0.4-0.5	6
0.5-0.6	1
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
0.5579	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