NPASS Compound

Natural Product: NPC473072

Natural Product ID	NPC473072
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XPZSTTGGUQPRPH-QMSXDKOZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3609097
PubChem CID	n.a.
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 78 83 0 0 0 0 0 0 0 0999 V2000 3.2807 0.0992 4.1018 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7261 -0.4242 2.7545 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2166 -0.2821 2.6393 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5340 0.2096 1.2258 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6972 -0.6079 0.2675 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2055 -0.3400 0.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0399 0.2801 1.7599 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6863 0.4641 -0.4772 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6488 -0.2106 -1.1126 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0682 -0.5222 -2.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9371 -0.1609 -3.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4550 1.2473 -3.3492 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6878 1.6815 -2.0473 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3882 0.5476 -1.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1750 1.0336 -0.0117 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5546 0.9610 0.0961 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2244 -0.0601 0.6684 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5743 -0.0087 0.6913 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2557 0.9803 0.1899 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6337 0.9702 0.2463 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3977 2.0011 -0.2741 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7849 3.0778 -0.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3935 3.1029 -0.9351 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6396 2.0559 -0.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2692 2.0525 -0.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6441 2.9898 -0.9783 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7244 4.1767 -1.5314 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7687 3.9526 -1.2996 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0232 3.5533 -0.8013 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7647 2.2400 -0.3506 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5713 -1.2108 1.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3784 -2.3103 1.5192 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9326 -3.4626 2.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5923 -3.4692 2.4668 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2330 -2.4079 2.2284 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2594 -1.2752 1.6231 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1243 -4.6435 3.0832 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7615 -4.5510 2.3712 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1220 -4.4312 1.9732 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0823 2.1792 -4.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7846 1.6449 -5.6350 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4624 -0.2479 -4.8130 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1629 0.2618 -2.9254 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9147 -1.9509 0.4786 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8662 0.0620 0.9223 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6434 0.6484 3.5850 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2862 -0.7483 4.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2646 0.5669 4.0617 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9663 0.8625 4.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4752 -1.5222 2.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7568 -1.2334 2.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2244 1.2793 1.2168 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9356 -0.2745 -0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6558 -1.2924 0.5545 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4885 -1.1891 -0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2701 -1.6024 -2.6956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1167 -0.9255 -3.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6681 1.2567 -3.4689 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3667 -0.0544 -1.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1074 0.1248 0.7138 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4130 4.0201 -2.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7964 3.5644 -1.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3535 4.2117 0.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4484 -2.2907 1.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2800 -2.4677 2.5221 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4219 -0.4140 1.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2786 -4.6686 4.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6485 -3.6090 2.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6176 -5.4212 2.1078 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1908 -4.2098 0.8734 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1894 2.1062 -4.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7049 3.1901 -4.2266 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3473 2.0615 -6.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3837 -1.1787 -5.1578 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2488 0.9762 -2.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8385 -2.5069 -0.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2674 0.8717 0.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6151 0.6203 3.7491 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 23 27 1 0 22 28 1 0 28 29 1 0 29 30 1 0 17 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 33 38 1 0 38 39 1 0 12 40 1 0 40 41 1 0 11 42 1 0 10 43 1 0 5 44 1 0 4 45 1 0 3 46 1 0 7 2 1 0 14 9 1 0 25 16 1 0 24 19 1 0 30 21 1 0 36 31 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 3 51 1 0 4 52 1 0 5 53 1 0 6 54 1 0 9 55 1 0 10 56 1 0 11 57 1 0 12 58 1 0 14 59 1 0 20 60 1 0 27 61 1 0 29 62 1 0 29 63 1 0 32 64 1 0 35 65 1 0 36 66 1 0 37 67 1 0 39 68 1 0 39 69 1 0 39 70 1 0 40 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 45 77 1 0 46 78 1 0 M END

Standard InCHIKey	XPZSTTGGUQPRPH-QMSXDKOZSA-N
Standard InCHI	InChI=1S/C29H32O17/c1-9-17(32)21(36)23(38)28(42-9)46-27-22(37)18(33)15(7-30)44-29(27)45-26-20(35)16-13(6-14-25(19(16)34)41-8-40-14)43-24(26)10-3-4-11(31)12(5-10)39-2/h3-6,9,15,17-18,21-23,27-34,36-38H,7-8H2,1-2H3/t9-,15+,17-,18+,21+,22-,23+,27+,28-,29-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC5=C(C(=C4C3=O)O)OCO5)C6=CC(=C(C=C6)O)OC)CO)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.16	Volume:	587.143 ? Van der Waals volume.
Dense:	1.111	LogP:	-0.446 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.584 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.143 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	34.0
TPSA:	256.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.908	Fsp³:	0.483
MCE-18:	136.953 ? 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:	0.246	Fluc inhibitor:	0.051 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.866 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.786 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.079	Promiscuous compounds:	0.24

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.39	MDCK Permeability:	-5.221
Pgp-inhibitor:	0.0	Pgp-substrate:	0.91
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):	0.991
20% Bioavailability (F20%):	0.404	30% Bioavailability (F30%):	0.971
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.885
Plasma Protein Binding (PPB):	75.095%	Volume Distribution (VD):	-0.226
Fu:	23.831% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.937	BCRP inhibitor:	0.609
BSEP inhibitor:	0.388

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.808	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.053
HLM stability:	0.0 ? 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):

1.437

Half-life (T1/2):

3.632

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.325
Human Hepatotoxicity (H-HT):	0.49	Drug-induced Liver Injury (DILI):	0.842
AMES Toxicity:	0.637	Rat Oral Acute Toxicity:	0.272
Maximum Recommended Daily Dose:	0.244	Skin Sensitization:	0.228
Carcinogencity:	0.302	Eye Corrosion:	0.0
Eye Irritation:	0.042	Respiratory Toxicity:	0.042
Drug-induced Neurotoxicity:	0.145	Ototoxicity:	0.961
Hematotoxicity:	0.081	Drug-induced Nephrotoxicity:	0.087
Genotoxicity:	0.287	RPMI-8226 Immunitoxicity:	0.131
A549 Cytotoxicity:	0.103	Hek293 Cytotoxicity:	0.634
BCF:	0.497 ? 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:	3.01 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.989 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.849 ? 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
NPO33494	atriplex littoralis	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26290401]
NPO33494	atriplex littoralis	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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

Activity Type	# Activity
Activity	15

Activity Type	# Activity
Cell line	15

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
NPT885	Cell line	PBL	n.a.	Activity	=	170.9	n.a.	PMID[21910504]
NPT885	Cell line	PBL	n.a.	Activity	=	172.0	n.a.	PMID[21910504]
NPT885	Cell line	PBL	n.a.	Activity	=	14.3	%	PMID[8864236]
NPT885	Cell line	PBL	n.a.	Activity	=	14.1	%	PMID[8410974]
NPT885	Cell line	PBL	n.a.	Activity	=	14.4	%	DrugMatrix in vitro pharmacology data
NPT885	Cell line	PBL	n.a.	Activity	=	1.7	n.a.	PMID[22901896]
NPT885	Cell line	PBL	n.a.	Activity	=	1.2	n.a.	PMID[23368966]
NPT885	Cell line	PBL	n.a.	Activity	=	175.3	n.a.	PMID[17253840]
NPT885	Cell line	PBL	n.a.	Activity	=	94.0	%	PMID[17371810]
NPT885	Cell line	PBL	n.a.	Activity	=	93.4	%	PMID[21377877]
NPT885	Cell line	PBL	n.a.	Activity	=	95.8	%	PMID[21377877]

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 NPC473072 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	22901
0.1-0.2	23118
0.2-0.3	3097
0.3-0.4	469
0.4-0.5	208
0.5-0.6	50
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.837	Intermediate Similarity	NPC473071
0.7423	Intermediate Similarity	NPC220173
0.7021	Intermediate Similarity	NPC473682
0.6907	Remote Similarity	NPC470444
0.6667	Remote Similarity	NPC240306
0.6458	Remote Similarity	NPC488072
0.6408	Remote Similarity	NPC195257
0.6214	Remote Similarity	NPC32641
0.6214	Remote Similarity	NPC256188
0.62	Remote Similarity	NPC163242
0.62	Remote Similarity	NPC272068
0.6168	Remote Similarity	NPC89052
0.6139	Remote Similarity	NPC155877
0.6058	Remote Similarity	NPC35119
0.5943	Remote Similarity	NPC473073
0.5758	Remote Similarity	NPC101026
0.5758	Remote Similarity	NPC488077
0.5644	Remote Similarity	NPC170052
0.5644	Remote Similarity	NPC135846
0.5625	Remote Similarity	NPC219043
0.5625	Remote Similarity	NPC173837
0.5588	Remote Similarity	NPC254855
0.5588	Remote Similarity	NPC94610
0.5556	Remote Similarity	NPC142142
0.5546	Remote Similarity	NPC192539
0.549	Remote Similarity	NPC476215
0.5455	Remote Similarity	NPC24043
0.5455	Remote Similarity	NPC27640
0.5439	Remote Similarity	NPC480441
0.5439	Remote Similarity	NPC25523
0.5437	Remote Similarity	NPC95866
0.5417	Remote Similarity	NPC175429
0.5405	Remote Similarity	NPC602448
0.5392	Remote Similarity	NPC223747
0.5377	Remote Similarity	NPC65003
0.537	Remote Similarity	NPC483414
0.5357	Remote Similarity	NPC14187
0.5347	Remote Similarity	NPC488071
0.534	Remote Similarity	NPC203050
0.534	Remote Similarity	NPC225434
0.5333	Remote Similarity	NPC209550
0.5327	Remote Similarity	NPC115674
0.5321	Remote Similarity	NPC482026
0.53	Remote Similarity	NPC603655
0.5294	Remote Similarity	NPC21666
0.5263	Remote Similarity	NPC488075
0.5243	Remote Similarity	NPC602805
0.5229	Remote Similarity	NPC480471
0.5229	Remote Similarity	NPC488076
0.5225	Remote Similarity	NPC476472
0.5225	Remote Similarity	NPC294815
0.5225	Remote Similarity	NPC16194
0.5222	Remote Similarity	NPC261004
0.5124	Remote Similarity	NPC488079
0.5096	Remote Similarity	NPC206123
0.5093	Remote Similarity	NPC304741
0.5091	Remote Similarity	NPC12013
0.5091	Remote Similarity	NPC11432
0.5091	Remote Similarity	NPC477613
0.5086	Remote Similarity	NPC48984
0.5082	Remote Similarity	NPC138990
0.5046	Remote Similarity	NPC255157
0.5046	Remote Similarity	NPC259896
0.5045	Remote Similarity	NPC122467

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5953
0.1-0.2	3156
0.2-0.3	33
0.3-0.4	4
0.4-0.5	4
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data