NPASS Compound

Natural Product: NPC473073

Natural Product ID	NPC473073
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JLVNQQVLSLMEHM-IHXONYQQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3609098
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 75 80 0 0 0 0 0 0 0 0999 V2000 -4.8777 2.3192 -1.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4573 2.1302 0.4013 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6562 1.7089 1.1979 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1979 1.5879 2.6301 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1505 0.5298 2.6738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4204 0.3067 1.4153 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4139 1.2702 0.4556 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 -0.8993 0.7880 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8447 -1.8093 0.6040 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7235 -1.4806 -0.3077 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2827 -1.4941 -1.7370 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0336 -1.6444 -2.6160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2522 -0.3620 -2.3212 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1298 -0.2359 -0.9057 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9444 -0.4055 -0.0266 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1208 -1.1528 -0.4623 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3333 -0.7023 0.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4706 -0.6405 -0.6730 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5816 -0.1545 -0.0669 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5627 0.2368 1.1766 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 0.7363 1.7900 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7099 1.1534 3.1018 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5449 1.0820 3.8356 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3935 0.5988 3.2727 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4172 0.1857 1.9577 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2602 -0.2948 1.3937 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1707 -0.3860 2.0113 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1930 0.5024 3.9626 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8150 1.5613 5.1151 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0305 2.3214 5.0339 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7103 1.6836 3.9427 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5796 -1.0634 -2.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6642 -0.6677 -2.8359 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8423 -1.1332 -4.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9303 -2.0150 -4.6827 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8742 -2.3971 -3.9123 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6950 -1.9312 -2.6101 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0775 -2.5063 -5.9927 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9093 -0.7608 -4.9422 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2692 0.6380 -2.5377 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4947 -1.6158 -3.9457 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0495 -2.6297 -1.9114 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2289 0.8141 3.7184 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2917 1.2807 3.4435 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6191 2.7353 1.1744 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1574 3.0281 -1.5349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8823 1.3890 -1.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8725 2.8057 -1.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1358 3.1265 0.7792 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1423 0.7994 0.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7658 2.5695 2.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6616 -0.4012 3.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3431 0.1301 1.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4033 -2.0514 1.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3375 -2.7315 0.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0353 -2.3797 -0.2897 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8378 -0.5749 -1.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5249 -2.5555 -2.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5132 -0.2577 -3.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5378 0.7931 -0.6921 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6276 0.7888 1.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 1.3741 4.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5977 2.2368 5.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7160 3.3508 4.7668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4187 0.0278 -2.4599 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1119 -3.0957 -4.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8150 -2.3333 -2.0791 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7527 -3.4568 -6.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3683 -1.5305 -5.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9870 1.4727 -2.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6279 -0.6617 -4.1661 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0501 -2.8641 -2.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4307 0.2913 3.4787 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1260 1.3205 2.9144 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5239 2.3893 1.0296 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 14 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 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 26 27 2 0 24 28 1 0 23 29 1 0 29 30 1 0 30 31 1 0 18 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 35 38 1 0 34 39 1 0 13 40 1 0 12 41 1 0 11 42 1 0 5 43 1 0 4 44 1 0 3 45 1 0 7 2 1 0 15 10 1 0 26 17 1 0 25 20 1 0 31 22 1 0 37 32 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 3 50 1 0 4 51 1 0 5 52 1 0 6 53 1 0 9 54 1 0 9 55 1 0 10 56 1 0 11 57 1 0 12 58 1 0 13 59 1 0 14 60 1 0 21 61 1 0 28 62 1 0 30 63 1 0 30 64 1 0 33 65 1 0 36 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 43 73 1 0 44 74 1 0 45 75 1 0 M END

Standard InCHIKey	JLVNQQVLSLMEHM-IHXONYQQSA-N
Standard InCHI	InChI=1S/C28H30O17/c1-8-16(31)20(35)22(37)27(42-8)39-6-14-17(32)21(36)23(38)28(44-14)45-26-19(34)15-12(5-13-25(18(15)33)41-7-40-13)43-24(26)9-2-3-10(29)11(30)4-9/h2-5,8,14,16-17,20-23,27-33,35-38H,6-7H2,1H3/t8-,14+,16-,17+,20+,21-,22+,23+,27+,28-/m0/s1
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC5=C(C(=C4C3=O)O)OCO5)C6=CC(=C(C=C6)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.15	Volume:	569.847 ? Van der Waals volume.
Dense:	1.12	LogP:	-0.136 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.506 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.62 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	34.0
TPSA:	267.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	17.0

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:	4.945	Fsp³:	0.464
MCE-18:	137.927 ? 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:	0.295	Fluc inhibitor:	0.053 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.916 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.881 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.059	Promiscuous compounds:	0.309

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.218	MDCK Permeability:	-5.102
Pgp-inhibitor:	0.0	Pgp-substrate:	0.828
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):	0.985
20% Bioavailability (F20%):	0.883	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.819
Plasma Protein Binding (PPB):	81.653%	Volume Distribution (VD):	-0.152
Fu:	20.537% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.815	BCRP inhibitor:	0.087
BSEP inhibitor:	0.028

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.054	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:	0.009
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):

1.915

Half-life (T1/2):

3.552

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.571
Human Hepatotoxicity (H-HT):	0.36	Drug-induced Liver Injury (DILI):	0.913
AMES Toxicity:	0.714	Rat Oral Acute Toxicity:	0.401
Maximum Recommended Daily Dose:	0.456	Skin Sensitization:	0.413
Carcinogencity:	0.176	Eye Corrosion:	0.0
Eye Irritation:	0.028	Respiratory Toxicity:	0.021
Drug-induced Neurotoxicity:	0.072	Ototoxicity:	0.978
Hematotoxicity:	0.02	Drug-induced Nephrotoxicity:	0.02
Genotoxicity:	0.722	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.334	Hek293 Cytotoxicity:	0.715
BCF:	0.512 ? 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:	3.035 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.108 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.915 ? 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	=	131.3	n.a.	PMID[21910504]
NPT885	Cell line	PBL	n.a.	Activity	=	126.6	n.a.	Open TG-GATES in vivo data: Hematology
NPT885	Cell line	PBL	n.a.	Activity	=	11.7	%	PMID[8864236]
NPT885	Cell line	PBL	n.a.	Activity	=	10.8	%	DrugMatrix in vitro pharmacology data
NPT885	Cell line	PBL	n.a.	Activity	=	11.2	%	PMID[23398362]
NPT885	Cell line	PBL	n.a.	Activity	=	1.6	n.a.	PMID[22901896]
NPT885	Cell line	PBL	n.a.	Activity	=	1.2	n.a.	PMID[25856683]
NPT885	Cell line	PBL	n.a.	Activity	=	141.4	n.a.	PMID[20329733]
NPT885	Cell line	PBL	n.a.	Activity	=	69.2	%	PMID[17371812]
NPT885	Cell line	PBL	n.a.	Activity	=	71.7	%	PMID[21377877]
NPT885	Cell line	PBL	n.a.	Activity	=	77.3	%	PMID[15921416]

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 NPC473073 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	21606
0.1-0.2	25068
0.2-0.3	2389
0.3-0.4	428
0.4-0.5	215
0.5-0.6	98
0.6-0.7	36
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7582	Intermediate Similarity	NPC126784
0.7582	Intermediate Similarity	NPC241423
0.75	Intermediate Similarity	NPC470443
0.7363	Intermediate Similarity	NPC203259
0.7363	Intermediate Similarity	NPC33054
0.7363	Intermediate Similarity	NPC176740
0.7363	Intermediate Similarity	NPC471725
0.7363	Intermediate Similarity	NPC134532
0.7363	Intermediate Similarity	NPC602582
0.7083	Intermediate Similarity	NPC473071
0.7011	Intermediate Similarity	NPC27640
0.6915	Remote Similarity	NPC186816
0.6737	Remote Similarity	NPC473571
0.6737	Remote Similarity	NPC110941
0.6702	Remote Similarity	NPC173582
0.6702	Remote Similarity	NPC265885
0.6702	Remote Similarity	NPC181465
0.6702	Remote Similarity	NPC215710
0.6702	Remote Similarity	NPC473438
0.6702	Remote Similarity	NPC253788
0.6667	Remote Similarity	NPC488073
0.6632	Remote Similarity	NPC65563
0.6632	Remote Similarity	NPC470949
0.6526	Remote Similarity	NPC39834
0.6495	Remote Similarity	NPC488074
0.6458	Remote Similarity	NPC156869
0.6354	Remote Similarity	NPC67326
0.6354	Remote Similarity	NPC67105
0.6289	Remote Similarity	NPC210073
0.6286	Remote Similarity	NPC480441
0.6275	Remote Similarity	NPC470446
0.6264	Remote Similarity	NPC271692
0.6263	Remote Similarity	NPC483414
0.6263	Remote Similarity	NPC483415
0.6238	Remote Similarity	NPC476472
0.6238	Remote Similarity	NPC294815
0.6238	Remote Similarity	NPC16194
0.62	Remote Similarity	NPC483416
0.62	Remote Similarity	NPC473327
0.6176	Remote Similarity	NPC470445
0.6129	Remote Similarity	NPC488071
0.6087	Remote Similarity	NPC305811
0.6042	Remote Similarity	NPC116864
0.6042	Remote Similarity	NPC244776
0.604	Remote Similarity	NPC122467
0.6038	Remote Similarity	NPC292019
0.6038	Remote Similarity	NPC202908
0.5943	Remote Similarity	NPC473072
0.5922	Remote Similarity	NPC89127
0.59	Remote Similarity	NPC204693
0.587	Remote Similarity	NPC127546
0.587	Remote Similarity	NPC57625
0.587	Remote Similarity	NPC173637
0.587	Remote Similarity	NPC317489
0.587	Remote Similarity	NPC223424
0.587	Remote Similarity	NPC600591
0.5833	Remote Similarity	NPC605784
0.5758	Remote Similarity	NPC471079
0.57	Remote Similarity	NPC44931
0.57	Remote Similarity	NPC227508
0.5688	Remote Similarity	NPC25523
0.5684	Remote Similarity	NPC59534
0.5673	Remote Similarity	NPC142142
0.5673	Remote Similarity	NPC486577
0.5657	Remote Similarity	NPC254540
0.5648	Remote Similarity	NPC470451
0.5614	Remote Similarity	NPC488078
0.5607	Remote Similarity	NPC14187
0.5579	Remote Similarity	NPC46420
0.5566	Remote Similarity	NPC470449
0.5556	Remote Similarity	NPC265115
0.5545	Remote Similarity	NPC303694
0.5532	Remote Similarity	NPC249281
0.551	Remote Similarity	NPC99957
0.5505	Remote Similarity	NPC189564
0.549	Remote Similarity	NPC233994
0.549	Remote Similarity	NPC605592
0.5481	Remote Similarity	NPC12013
0.5481	Remote Similarity	NPC11432
0.5481	Remote Similarity	NPC477613
0.5474	Remote Similarity	NPC158674
0.5474	Remote Similarity	NPC136042
0.5472	Remote Similarity	NPC470447
0.5472	Remote Similarity	NPC471669
0.5472	Remote Similarity	NPC483412
0.5455	Remote Similarity	NPC276377
0.5431	Remote Similarity	NPC241781
0.5429	Remote Similarity	NPC37668
0.5417	Remote Similarity	NPC24043
0.5413	Remote Similarity	NPC203145
0.5361	Remote Similarity	NPC42773
0.5361	Remote Similarity	NPC45522
0.534	Remote Similarity	NPC22062
0.534	Remote Similarity	NPC473634
0.534	Remote Similarity	NPC138811
0.5333	Remote Similarity	NPC211532
0.5333	Remote Similarity	NPC488364
0.5327	Remote Similarity	NPC483413
0.5321	Remote Similarity	NPC81042
0.5283	Remote Similarity	NPC209296
0.5278	Remote Similarity	NPC221342
0.5278	Remote Similarity	NPC476470
0.5263	Remote Similarity	NPC111929
0.5263	Remote Similarity	NPC320283
0.5263	Remote Similarity	NPC41121
0.5259	Remote Similarity	NPC156785
0.5259	Remote Similarity	NPC162394
0.5248	Remote Similarity	NPC95866
0.5229	Remote Similarity	NPC223426
0.5229	Remote Similarity	NPC602448
0.52	Remote Similarity	NPC116458
0.52	Remote Similarity	NPC246943
0.5194	Remote Similarity	NPC482521
0.5192	Remote Similarity	NPC150164
0.5182	Remote Similarity	NPC470455
0.5155	Remote Similarity	NPC145038
0.5155	Remote Similarity	NPC56077
0.5155	Remote Similarity	NPC281131
0.5155	Remote Similarity	NPC253662
0.5155	Remote Similarity	NPC179950
0.5155	Remote Similarity	NPC88789
0.5155	Remote Similarity	NPC491374
0.5152	Remote Similarity	NPC175107
0.5152	Remote Similarity	NPC611303
0.5149	Remote Similarity	NPC488072
0.5146	Remote Similarity	NPC480466
0.5146	Remote Similarity	NPC187379
0.5135	Remote Similarity	NPC89052
0.5135	Remote Similarity	NPC121703
0.5104	Remote Similarity	NPC135599
0.5104	Remote Similarity	NPC73855
0.5104	Remote Similarity	NPC113968
0.5104	Remote Similarity	NPC328940
0.5104	Remote Similarity	NPC277174
0.5104	Remote Similarity	NPC606877
0.5102	Remote Similarity	NPC84362
0.5098	Remote Similarity	NPC172807
0.5094	Remote Similarity	NPC153755
0.5085	Remote Similarity	NPC480444
0.5077	Remote Similarity	NPC482520
0.5077	Remote Similarity	NPC482519
0.5052	Remote Similarity	NPC238376
0.5048	Remote Similarity	NPC155877
0.5047	Remote Similarity	NPC65711
0.5044	Remote Similarity	NPC173837

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473073 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5605
0.1-0.2	3497
0.2-0.3	38
0.3-0.4	5
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
0.7-0.8	2
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
0.7363	Intermediate Similarity	NPD6797	Phase 2
0.7263	Intermediate Similarity	NPD7251	Phase 2
0.6154	Remote Similarity	NPD7808	Phase 3
0.5283	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