NPASS Compound

Natural Product: NPC480080

Natural Product ID	NPC480080
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZUDUTMXXOVZHHX-ILJGUCPLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44584187
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 109109 0 0 0 0 0 0 0 0999 V2000 12.8061 -2.6631 -2.9077 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3930 -3.1834 -2.7241 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6138 -2.1702 -1.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6239 -0.8818 -2.5768 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0443 0.3230 -1.9955 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6383 0.4755 -1.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0252 -0.3906 -0.5979 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6897 -0.3601 0.7126 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9083 0.8362 1.4956 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9573 1.7390 2.1042 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9614 2.5848 1.4926 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7888 2.1082 0.7321 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9130 1.1787 1.5619 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7232 0.7859 0.7162 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9559 -0.3538 1.3739 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5010 0.0638 2.7726 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6198 1.2378 2.7517 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3895 1.3307 3.2101 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2723 0.1853 3.8338 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5658 -0.1913 3.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 0.8975 3.1444 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0187 1.4771 2.0349 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6309 1.0888 0.6856 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6231 0.5415 -0.2382 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7824 1.2852 -0.7444 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7312 1.7979 0.2670 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 2.5064 -0.3031 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8327 1.6086 -1.1328 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3505 0.4513 -0.3430 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2360 -0.4983 -1.1706 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4159 0.2470 -1.6946 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3117 -0.5795 -2.5387 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8582 -1.7735 -1.8695 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1540 -1.9274 -1.5772 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4059 -3.2137 -0.9123 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7890 -2.9265 0.5334 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1719 -3.8686 -0.9752 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1985 -3.0158 -1.4946 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0071 -3.3372 -1.5906 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1773 0.7396 -0.6050 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4954 0.3691 -1.5776 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2415 0.2417 -0.4636 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6367 0.0355 1.8447 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0201 -2.0582 -1.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4851 -3.5512 -2.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8929 -2.0708 -3.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8845 -3.3097 -3.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4422 -4.1491 -2.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6468 -2.6397 -1.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1694 -2.1424 -0.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7307 -0.6396 -2.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2281 -1.0235 -3.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7335 0.6089 -1.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3169 1.1849 -2.7202 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0039 0.3954 -2.5809 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4095 1.5451 -1.3090 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9486 -0.1615 -0.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9942 -1.4800 -0.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6652 -0.9952 0.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0711 -1.0779 1.3788 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6479 1.5462 0.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6939 0.5650 2.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3850 1.0855 2.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5709 2.3979 2.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6048 3.3266 2.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5019 3.3151 0.7882 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0185 1.7522 -0.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1471 3.0605 0.5766 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6112 1.7424 2.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0319 1.5829 0.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0457 -0.5038 0.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5147 -1.2927 1.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0630 -0.8472 3.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3991 0.2777 3.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0398 2.1587 2.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1354 2.3093 3.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2967 -0.7369 3.9335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5144 0.4937 4.8972 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4121 -0.6845 2.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9938 -1.0179 3.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9220 1.2980 4.0958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7097 2.2867 2.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7153 0.4444 0.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2291 2.0502 0.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0151 0.1632 -1.1492 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0362 -0.4622 0.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4878 2.0922 -1.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2283 2.6562 0.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0464 1.0793 1.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6552 3.3688 -0.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5405 2.8839 0.5470 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4346 1.3653 -2.1196 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7480 2.2557 -1.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5569 -0.1682 0.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9917 0.7731 0.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6404 -1.1947 -0.3739 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6449 -0.9812 -1.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1092 1.1295 -2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6813 -0.9394 -3.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1427 0.0446 -2.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9076 -1.1776 -1.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2301 -3.7789 -1.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6111 -3.6437 0.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8862 -3.0968 1.1505 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1048 -1.8872 0.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8525 1.6374 -0.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3421 -0.5594 -1.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9527 -0.6882 -0.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4464 -0.7186 1.2662 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 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 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 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 31 40 1 0 25 41 1 0 14 42 1 0 13 43 1 0 38 33 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 1 14 70 1 6 15 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 0 18 76 1 0 19 77 1 0 19 78 1 0 20 79 1 0 20 80 1 0 21 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 26 88 1 0 26 89 1 0 27 90 1 0 27 91 1 0 28 92 1 0 28 93 1 0 29 94 1 0 29 95 1 0 30 96 1 0 30 97 1 0 31 98 1 0 32 99 1 0 32100 1 0 34101 1 0 35102 1 0 36103 1 0 36104 1 0 36105 1 0 40106 1 0 41107 1 0 42108 1 0 43109 1 0 M END

Standard InCHIKey	ZUDUTMXXOVZHHX-ILJGUCPLSA-N
Standard InCHI	InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-13-16-22-27-35(40)36(41)28-23-17-14-11-10-12-15-19-24-33(38)25-20-18-21-26-34(39)30-32-29-31(2)43-37(32)42/h12,14-15,17,29,31,33-36,38-41H,3-11,13,16,18-28,30H2,1-2H3/b15-12-,17-14-/t31?,33?,34?,35-,36-/m0/s1
SMILES	CCCCCCCCCCCC[C@@H]([C@H](CC/C=CCC/C=CCCC(CCCCCC(CC1=CC(C)OC1=O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	606.49	Volume:	682.147 ? Van der Waals volume.
Dense:	0.889	LogP:	7.87 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.598 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.749 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	29.0	Rigid Bonds:	8.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	1.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.039	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.513	Fsp³:	0.811
MCE-18:	20.299 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.679	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.035 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.024 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.639	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.074	MDCK Permeability:	-4.75
Pgp-inhibitor:	0.002	Pgp-substrate:	0.003
PAMPA:	0.002 ? 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):	0.987
20% Bioavailability (F20%):	0.796	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.921
Plasma Protein Binding (PPB):	97.296%	Volume Distribution (VD):	-0.129
Fu:	2.124% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.041
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.363
BSEP inhibitor:	0.97

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.03	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.957	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.065	CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.883
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.075 ? 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):

6.198

Half-life (T1/2):

0.635

ADMET: Toxicity

hERG Blockers:	0.531	hERG Blockers (10um):	0.844
Human Hepatotoxicity (H-HT):	0.393	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.015	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.71	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.017
Eye Irritation:	0.642	Respiratory Toxicity:	0.734
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.92
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.868	Hek293 Cytotoxicity:	0.341
BCF:	1.077 ? 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:	5.209 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.517 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.267 ? 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
NPO40783	Annona coriaceae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778244]

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
ED50	2

Activity Type	# Activity
Cell line	2

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
NPT189	Cell line	Vero	Chlorocebus aethiops	ED50	=	1.5	10'-1 ug/ml	PMID[8778244]
NPT91	Cell line	KB	Homo sapiens	ED50	=	1.6	10'-6 ug/ml	PMID[8778244]

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 NPC480080 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	16919
0.1-0.2	29244
0.2-0.3	3283
0.3-0.4	201
0.4-0.5	63
0.5-0.6	60
0.6-0.7	69
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9111	High Similarity	NPC488246
0.7843	Intermediate Similarity	NPC488244
0.7674	Intermediate Similarity	NPC608138
0.7407	Intermediate Similarity	NPC480081
0.7115	Intermediate Similarity	NPC488250
0.7059	Intermediate Similarity	NPC480079
0.6981	Remote Similarity	NPC69082
0.6981	Remote Similarity	NPC488249
0.6863	Remote Similarity	NPC134865
0.6863	Remote Similarity	NPC103523
0.6863	Remote Similarity	NPC488627
0.6863	Remote Similarity	NPC488631
0.661	Remote Similarity	NPC279267
0.66	Remote Similarity	NPC107986
0.66	Remote Similarity	NPC223871
0.66	Remote Similarity	NPC231009
0.66	Remote Similarity	NPC103284
0.66	Remote Similarity	NPC110710
0.66	Remote Similarity	NPC1083
0.66	Remote Similarity	NPC82795
0.66	Remote Similarity	NPC286338
0.66	Remote Similarity	NPC603931
0.66	Remote Similarity	NPC604237
0.6538	Remote Similarity	NPC477011
0.6471	Remote Similarity	NPC488253
0.6471	Remote Similarity	NPC473669
0.6471	Remote Similarity	NPC488251
0.64	Remote Similarity	NPC606043
0.6364	Remote Similarity	NPC473478
0.6364	Remote Similarity	NPC473651
0.6364	Remote Similarity	NPC66346
0.6346	Remote Similarity	NPC232555
0.6346	Remote Similarity	NPC171174
0.6346	Remote Similarity	NPC182383
0.6346	Remote Similarity	NPC114694
0.6346	Remote Similarity	NPC485248
0.6346	Remote Similarity	NPC142117
0.6346	Remote Similarity	NPC480249
0.6346	Remote Similarity	NPC485249
0.6346	Remote Similarity	NPC240695
0.625	Remote Similarity	NPC231096
0.625	Remote Similarity	NPC475581
0.625	Remote Similarity	NPC283085
0.625	Remote Similarity	NPC62118
0.625	Remote Similarity	NPC107717
0.625	Remote Similarity	NPC488252
0.6226	Remote Similarity	NPC93794
0.6226	Remote Similarity	NPC488632
0.6226	Remote Similarity	NPC473504
0.6226	Remote Similarity	NPC81778
0.6226	Remote Similarity	NPC40066
0.6226	Remote Similarity	NPC47937
0.62	Remote Similarity	NPC112685
0.6182	Remote Similarity	NPC600188
0.617	Remote Similarity	NPC609415
0.614	Remote Similarity	NPC233551
0.614	Remote Similarity	NPC40376
0.614	Remote Similarity	NPC21208
0.6038	Remote Similarity	NPC81045
0.6038	Remote Similarity	NPC39754
0.6038	Remote Similarity	NPC171135
0.6038	Remote Similarity	NPC61257
0.6038	Remote Similarity	NPC320569
0.6038	Remote Similarity	NPC133730
0.6038	Remote Similarity	NPC191929
0.6038	Remote Similarity	NPC100454
0.6038	Remote Similarity	NPC242364
0.6038	Remote Similarity	NPC172821
0.6038	Remote Similarity	NPC274446
0.6038	Remote Similarity	NPC485251
0.6038	Remote Similarity	NPC151403
0.6038	Remote Similarity	NPC261952
0.6038	Remote Similarity	NPC605171
0.6	Remote Similarity	NPC178215
0.6	Remote Similarity	NPC42598
0.5965	Remote Similarity	NPC132496
0.5965	Remote Similarity	NPC606740
0.5965	Remote Similarity	NPC608614
0.5932	Remote Similarity	NPC91067
0.5893	Remote Similarity	NPC309211
0.5862	Remote Similarity	NPC480082
0.5818	Remote Similarity	NPC280621
0.5818	Remote Similarity	NPC48338
0.5818	Remote Similarity	NPC488628
0.5789	Remote Similarity	NPC473707
0.5789	Remote Similarity	NPC20339
0.5714	Remote Similarity	NPC473687
0.5714	Remote Similarity	NPC204686
0.5714	Remote Similarity	NPC219498
0.5714	Remote Similarity	NPC308412
0.5714	Remote Similarity	NPC134885
0.5714	Remote Similarity	NPC488247
0.5714	Remote Similarity	NPC210218
0.5714	Remote Similarity	NPC488248
0.5645	Remote Similarity	NPC488245
0.5614	Remote Similarity	NPC329838
0.5614	Remote Similarity	NPC20621
0.5614	Remote Similarity	NPC318963
0.5614	Remote Similarity	NPC602738
0.5614	Remote Similarity	NPC605101
0.5574	Remote Similarity	NPC253801
0.5424	Remote Similarity	NPC169511
0.5424	Remote Similarity	NPC287164
0.5424	Remote Similarity	NPC234077
0.5424	Remote Similarity	NPC130359
0.5424	Remote Similarity	NPC14901
0.537	Remote Similarity	NPC329829
0.537	Remote Similarity	NPC100921
0.537	Remote Similarity	NPC475159
0.537	Remote Similarity	NPC131002
0.537	Remote Similarity	NPC473780
0.537	Remote Similarity	NPC477018
0.537	Remote Similarity	NPC604521
0.5357	Remote Similarity	NPC607439
0.5345	Remote Similarity	NPC134807
0.5333	Remote Similarity	NPC488623
0.5333	Remote Similarity	NPC488624
0.5333	Remote Similarity	NPC488629
0.5246	Remote Similarity	NPC239517
0.5179	Remote Similarity	NPC156804
0.5161	Remote Similarity	NPC488630
0.5161	Remote Similarity	NPC488625
0.5161	Remote Similarity	NPC322529
0.5161	Remote Similarity	NPC488626
0.5088	Remote Similarity	NPC473649
0.5088	Remote Similarity	NPC473156
0.5088	Remote Similarity	NPC154097
0.5088	Remote Similarity	NPC159750
0.5088	Remote Similarity	NPC73248
0.5088	Remote Similarity	NPC282815
0.5088	Remote Similarity	NPC470401
0.5088	Remote Similarity	NPC600524
0.5088	Remote Similarity	NPC600956
0.5088	Remote Similarity	NPC608355
0.5088	Remote Similarity	NPC610454

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480080 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6441
0.1-0.2	2616
0.2-0.3	91
0.3-0.4	2
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