NPASS Compound

Natural Product: NPC480472

Natural Product ID	NPC480472
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XBXPWZFHCUFBQM-YJCKAOSSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 96101 0 0 0 0 0 0 0 0999 V2000 10.3144 -2.1067 2.4792 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2160 -0.8791 2.0380 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6774 0.1296 1.3811 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4758 -0.0198 0.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8957 1.0089 -0.0459 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5487 2.2440 0.0139 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7033 2.4121 0.7189 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2779 1.3729 1.4047 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4641 1.5872 2.1186 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6651 0.8837 -0.7941 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0128 -0.2397 -1.0232 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7718 -0.3464 -1.7703 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3576 -1.6085 -1.8766 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0007 0.4545 -2.3284 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1414 1.2287 -2.9361 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4842 2.2864 -2.0191 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1847 2.7267 -2.5505 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2751 2.7788 -1.5133 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6027 1.9530 -0.5108 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0526 1.5756 -0.7251 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7735 2.0232 0.3754 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1966 0.8184 -0.4489 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7363 0.5693 0.8060 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1678 -0.5889 1.3315 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0770 -1.8004 0.4693 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4996 -1.9961 0.0735 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8677 -3.3917 0.6772 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7023 -3.2109 2.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3803 -1.1464 0.5730 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1253 0.1696 0.8586 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0286 1.0067 0.0967 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3843 0.6439 0.1432 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1673 1.0466 1.2352 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6844 1.7310 2.1538 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4995 0.6912 1.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0050 -0.0546 0.2983 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3383 -0.4337 0.3566 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1348 -0.0534 1.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6425 0.6972 2.4832 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2947 1.0723 2.4054 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7764 1.8213 3.4205 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4309 1.0659 3.5552 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5852 0.2582 4.7061 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4706 -0.4621 1.4581 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2629 -0.4338 -0.7400 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9690 -0.0933 -0.8283 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2703 -0.5821 -2.0388 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0537 -0.1583 -2.4418 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4384 -0.7089 -3.5834 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0445 -1.6871 -4.3225 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3006 -2.1243 -3.9050 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8809 -1.5834 -2.8018 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9228 -3.1303 -4.6612 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4766 -2.2661 -5.4592 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6530 -1.6669 -0.7405 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0728 -0.8533 2.6643 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4115 3.2095 -1.6380 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7046 1.9073 -4.0244 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1306 -2.1699 3.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4013 -2.5460 2.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5781 -2.8978 1.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0382 -1.0111 0.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0903 3.0427 -0.5163 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2215 3.3745 0.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9638 0.7520 2.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2066 1.7900 -1.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5015 -1.1319 -0.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2545 0.6472 -3.3580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2349 3.7164 -3.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8602 2.0284 -3.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4998 2.4276 0.5064 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2564 0.5221 -0.8622 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8694 3.0166 0.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4700 1.3958 1.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2160 -0.2906 1.2123 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3876 -2.6664 0.9877 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6020 -2.2050 -1.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8954 -3.6549 0.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1281 -4.1150 0.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1299 -3.9661 2.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5983 0.2664 1.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7244 -1.0180 -0.4524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0183 1.6361 4.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2919 0.6811 5.4395 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8733 -0.7750 4.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5983 0.1908 5.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1328 0.2286 1.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5288 0.6329 -1.9148 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4615 -0.3443 -3.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8733 -1.9494 -2.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7754 -3.1340 -5.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2710 -3.2679 -5.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0604 -1.3265 -1.4637 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7546 -1.2699 3.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5483 3.8955 -2.3475 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1865 1.7475 -4.8565 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 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 39 42 1 0 42 43 1 0 38 44 1 0 36 45 1 0 45 46 1 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 51 53 1 0 50 54 1 0 25 55 1 0 24 56 1 0 16 57 1 1 15 58 1 0 8 3 1 0 20 16 1 0 30 23 1 0 46 32 2 0 52 47 1 0 40 35 1 0 1 59 1 0 1 60 1 0 1 61 1 0 4 62 1 0 6 63 1 0 7 64 1 0 9 65 1 0 10 66 1 0 11 67 1 0 15 68 1 0 17 69 1 0 17 70 1 0 19 71 1 1 20 72 1 6 21 73 1 0 23 74 1 1 24 75 1 1 25 76 1 1 26 77 1 6 27 78 1 0 27 79 1 0 28 80 1 0 30 81 1 1 37 82 1 0 41 83 1 0 43 84 1 0 43 85 1 0 43 86 1 0 44 87 1 0 48 88 1 0 49 89 1 0 52 90 1 0 53 91 1 0 54 92 1 0 55 93 1 0 56 94 1 0 57 95 1 0 58 96 1 0 M END

Standard InCHIKey	XBXPWZFHCUFBQM-YJCKAOSSSA-N
Standard InCHI	InChI=1S/C37H38O21/c1-51-20-9-14(3-6-17(20)40)4-8-23(43)56-36(49)37(50)13-53-35(33(37)48)58-32-28(47)25(44)22(12-38)55-34(32)57-31-27(46)24-21(11-19(42)30(52-2)26(24)45)54-29(31)15-5-7-16(39)18(41)10-15/h3-11,22,25,28,32-36,38-42,44-45,47-50H,12-13H2,1-2H3/b8-4+/t22-,25-,28+,32-,33+,34-,35+,36?,37-/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC([C@]1(CO[C@H]([C@@H]1O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@@H]1Oc1c(=O)c2c(cc(c(c2O)OC)O)oc1c1ccc(c(c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	818.19	Volume:	747.49 ? Van der Waals volume.
Dense:	1.095	LogP:	0.873 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.277 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.604 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	37.0
TPSA:	334.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.036	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.406	Fsp³:	0.351
MCE-18:	147.84 ? 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:	1
Colloidal aggregators:	0.667	Fluc inhibitor:	0.347 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.888 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.192	Promiscuous compounds:	0.432

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.321	MDCK Permeability:	-5.481
Pgp-inhibitor:	0.0	Pgp-substrate:	0.056
PAMPA:	0.984 ? 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):	0.315
20% Bioavailability (F20%):	0.955	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.008
Plasma Protein Binding (PPB):	79.044%	Volume Distribution (VD):	-0.147
Fu:	16.631% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.523
BSEP inhibitor:	0.213

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:	0.004	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.918 ? 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):

1.51

Half-life (T1/2):

4.545

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.199
Human Hepatotoxicity (H-HT):	0.397	Drug-induced Liver Injury (DILI):	0.726
AMES Toxicity:	0.696	Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.166	Skin Sensitization:	1.0
Carcinogencity:	0.052	Eye Corrosion:	0.0
Eye Irritation:	0.143	Respiratory Toxicity:	0.015
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.976
Hematotoxicity:	0.024	Drug-induced Nephrotoxicity:	0.468
Genotoxicity:	0.48	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.761	Hek293 Cytotoxicity:	0.403
BCF:	0.606 ? 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:	3.307 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.024 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.269 ? 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
NPO40039	Atriplex tatarica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181926]

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
MIC	4
MBC	4
Inhibition	2

Activity Type	# Activity
Organism	10

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
NPT3888	Organism	Micrococcus flavus	Micrococcus flavus	MIC	=	311700.0	nM	PMID[31181926]
NPT3888	Organism	Micrococcus flavus	Micrococcus flavus	MBC	=	623.4	uM	PMID[31181926]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	935200.0	nM	PMID[31181926]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MBC	=	1246.9	uM	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	311700.0	nM	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MBC	=	623.4	uM	PMID[31181926]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	498700.0	nM	PMID[31181926]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	623.4	uM	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	20.1	%	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	4.3	%	PMID[31181926]

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 NPC480472 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	17752
0.1-0.2	28546
0.2-0.3	2875
0.3-0.4	484
0.4-0.5	160
0.5-0.6	29
0.6-0.7	5
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	Natural Product ID
0.7282	Intermediate Similarity	NPC480471
0.7282	Intermediate Similarity	NPC488076
0.7094	Intermediate Similarity	NPC480470
0.6757	Remote Similarity	NPC488075
0.6667	Remote Similarity	NPC21359
0.6667	Remote Similarity	NPC460984
0.6179	Remote Similarity	NPC25946
0.6031	Remote Similarity	NPC487501
0.595	Remote Similarity	NPC470713
0.5772	Remote Similarity	NPC470719
0.5772	Remote Similarity	NPC470717
0.5763	Remote Similarity	NPC470416
0.5738	Remote Similarity	NPC295625
0.5726	Remote Similarity	NPC470720
0.5726	Remote Similarity	NPC488078
0.5669	Remote Similarity	NPC199172
0.5625	Remote Similarity	NPC35924
0.5575	Remote Similarity	NPC470444
0.5517	Remote Similarity	NPC472991
0.5514	Remote Similarity	NPC42773
0.5514	Remote Similarity	NPC45522
0.5481	Remote Similarity	NPC487500
0.5439	Remote Similarity	NPC255157
0.5439	Remote Similarity	NPC259896
0.5391	Remote Similarity	NPC488073
0.5323	Remote Similarity	NPC470718
0.5299	Remote Similarity	NPC487502
0.5268	Remote Similarity	NPC254855
0.5268	Remote Similarity	NPC94610
0.5167	Remote Similarity	NPC36138
0.5161	Remote Similarity	NPC470712
0.5128	Remote Similarity	NPC253521
0.5128	Remote Similarity	NPC472992
0.5128	Remote Similarity	NPC113836
0.5116	Remote Similarity	NPC488079
0.5086	Remote Similarity	NPC155877
0.504	Remote Similarity	NPC164704

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4724
0.1-0.2	4383
0.2-0.3	38
0.3-0.4	5
0.4-0.5	0
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