NPASS Compound

Natural Product: NPC486127

Natural Product ID	NPC486127
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YYVUKSZYTNVDIA-UKHOAQRHSA-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 102108 0 0 0 0 0 0 0 0999 V2000 4.6491 1.8723 -1.9077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3402 0.3866 -1.8246 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6969 -0.1529 -0.4549 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2075 -1.5836 -0.3847 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7319 -1.6210 -0.6870 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2016 -0.2822 -1.1935 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0574 0.1020 -2.2215 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9751 -0.5526 -1.7744 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0867 0.1837 -1.2479 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7253 1.0824 -2.2364 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0236 1.5674 -1.6284 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0228 0.4339 -1.6712 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3850 -0.8830 -1.3026 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2360 -1.7239 -0.3799 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6864 -1.7633 -0.7682 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2299 -0.4535 -1.2105 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2152 0.6059 -0.8033 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9112 1.9280 -0.9373 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8985 1.9984 0.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8462 0.8332 0.2617 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2484 1.3822 0.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7179 -0.0003 1.4819 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5685 -1.2084 1.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4557 -1.3282 -0.3928 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6264 -0.1543 -0.8631 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2845 0.3733 -1.9816 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1114 0.6388 2.7595 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2552 0.7425 3.7644 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8963 1.4049 4.8925 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3497 1.6664 6.0280 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1734 1.6810 4.4917 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3642 1.2351 3.1887 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0705 -0.6969 -0.5823 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5374 -2.6200 -1.6429 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3999 -2.1246 0.8912 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2470 -3.2312 0.8467 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0687 -0.0852 -0.2218 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4201 0.6746 0.8674 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3362 1.8230 0.5128 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4857 1.3087 -0.3046 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7986 -0.1046 0.1356 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4129 -0.2742 1.5903 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8214 -1.6932 1.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1951 -1.7926 1.7547 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0597 -0.1539 1.8016 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1578 -0.3037 0.0299 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3229 1.4456 -1.6622 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7994 2.4014 1.6769 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6890 2.0069 -2.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9951 2.2675 -2.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4636 2.3902 -0.9488 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0278 -0.1166 -2.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1725 0.4387 0.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7981 -2.1946 -1.1020 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1862 -1.8278 0.2489 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1785 0.4722 -0.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3990 0.8295 -0.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9479 0.6021 -3.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1322 1.9891 -2.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7962 1.9260 -0.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3531 2.4304 -2.2424 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3527 0.3630 -2.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1888 -1.4909 -2.2048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8711 -2.7687 -0.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1130 -1.3413 0.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7547 -2.5447 -1.5841 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2289 -2.2230 0.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1480 -0.4731 -2.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8913 0.5153 0.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2626 2.7999 -0.8811 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5288 1.9752 -1.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4348 2.9789 0.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2997 1.9887 1.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9920 0.8078 0.7056 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5552 1.2582 -0.9374 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2793 2.4796 0.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6769 -0.3885 1.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6080 -1.1052 1.4697 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1597 -2.1228 1.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0960 -2.2978 -0.7290 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5166 -1.2418 -0.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8497 0.0066 -2.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2068 0.3885 3.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2459 0.5609 3.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6188 2.1786 2.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5947 -1.7028 -0.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2369 -0.3241 0.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8908 -3.4559 -1.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3675 -3.6208 1.8760 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1967 -2.9593 0.3620 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7197 -4.0335 0.2767 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5458 1.1181 1.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7379 2.5902 -0.0206 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3827 1.9279 -0.0223 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2630 -0.8678 -0.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9872 0.4546 2.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3340 -2.3931 1.2765 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5229 -1.9288 3.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3724 -2.7602 1.5846 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3416 -0.9490 -0.6957 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1344 1.5979 -2.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7002 2.8059 1.5905 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 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 22 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 13 33 1 0 5 34 1 0 4 35 1 0 35 36 1 0 3 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 40 47 1 0 39 48 1 0 7 2 1 0 33 9 1 0 45 38 1 0 17 12 1 0 25 20 1 0 32 27 1 0 25 16 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 6 3 53 1 1 4 54 1 6 5 55 1 1 6 56 1 1 9 57 1 1 10 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 12 62 1 6 13 63 1 6 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 16 68 1 6 17 69 1 1 18 70 1 0 18 71 1 0 19 72 1 0 19 73 1 0 21 74 1 0 21 75 1 0 21 76 1 0 22 77 1 1 23 78 1 0 23 79 1 0 24 80 1 0 24 81 1 0 26 82 1 0 28 83 1 0 32 84 1 0 32 85 1 0 33 86 1 0 33 87 1 0 34 88 1 0 36 89 1 0 36 90 1 0 36 91 1 0 38 92 1 1 39 93 1 6 40 94 1 1 41 95 1 6 42 96 1 1 43 97 1 0 43 98 1 0 44 99 1 0 46100 1 0 47101 1 0 48102 1 0 M END

Standard InCHIKey	YYVUKSZYTNVDIA-UKHOAQRHSA-N
Standard InCHI	InChI=1S/C35H54O13/c1-16-30(48-32-28(40)27(39)26(38)24(14-36)47-32)31(43-3)29(41)33(45-16)46-19-5-6-20-17(12-19)4-7-23-21(20)8-10-34(2)22(9-11-35(23,34)42)18-13-25(37)44-15-18/h13,16-17,19-24,26-33,36,38-42H,4-12,14-15H2,1-3H3/t16-,17+,19-,20-,21+,22+,23+,24-,26-,27+,28-,29-,30-,31-,32+,33-,34+,35-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@H]1CC[C@H]2[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)O)OC)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.36	Volume:	663.021 ? Van der Waals volume.
Dense:	1.029	LogP:	0.96 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.53 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.855 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	38.0
TPSA:	193.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.161	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.609	Fsp³:	0.914
MCE-18:	127.612 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.796	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.163	Promiscuous compounds:	0.283

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.417	MDCK Permeability:	-5.22
Pgp-inhibitor:	0.002	Pgp-substrate:	0.933
PAMPA:	0.972 ? 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):	0.24
20% Bioavailability (F20%):	0.194	30% Bioavailability (F30%):	0.781
50% Bioavailability (F50%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027	MRP1:	0.1
Plasma Protein Binding (PPB):	68.503%	Volume Distribution (VD):	-0.398
Fu:	27.528% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.155
BSEP inhibitor:	0.134

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.219
HLM stability:	0.184 ? 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):

1.036

Half-life (T1/2):

3.397

ADMET: Toxicity

hERG Blockers:	0.045	hERG Blockers (10um):	0.365
Human Hepatotoxicity (H-HT):	0.668	Drug-induced Liver Injury (DILI):	0.956
AMES Toxicity:	0.945	Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.994	Skin Sensitization:	1.0
Carcinogencity:	0.72	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.851
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.936
Hematotoxicity:	0.824	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.879
A549 Cytotoxicity:	0.798	Hek293 Cytotoxicity:	0.974
BCF:	0.9 ? 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:	3.286 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.726 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.928 ? 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
NPO8402	Thevetia peruviana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26714048]
NPO8402	Thevetia peruviana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39027575]
NPO8402	Thevetia peruviana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8402	Thevetia peruviana	Species	Apocynaceae	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

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell line	1
Non-molecular	2
Others	1

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
NPT1312	Cell line	SW1990	Homo sapiens	IC50	=	8100.0	nM	PMID[26714048]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3350.0	nM	PMID[26714048]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[26714048]
NPT27	Others	Unspecified	n.a.	IC50	>	10000.0	nM	PMID[26714048]

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 NPC486127 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	12196
0.1-0.2	32396
0.2-0.3	4471
0.3-0.4	607
0.4-0.5	72
0.5-0.6	54
0.6-0.7	41
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
0.9294	High Similarity	NPC486128
0.7841	Intermediate Similarity	NPC486130
0.7667	Intermediate Similarity	NPC486143
0.7667	Intermediate Similarity	NPC486135
0.7667	Intermediate Similarity	NPC486142
0.7667	Intermediate Similarity	NPC486137
0.7667	Intermediate Similarity	NPC486149
0.7582	Intermediate Similarity	NPC232785
0.7582	Intermediate Similarity	NPC486139
0.7363	Intermediate Similarity	NPC475629
0.734	Intermediate Similarity	NPC486132
0.734	Intermediate Similarity	NPC486131
0.7188	Intermediate Similarity	NPC486144
0.7188	Intermediate Similarity	NPC486145
0.7188	Intermediate Similarity	NPC486147
0.7188	Intermediate Similarity	NPC486136
0.7188	Intermediate Similarity	NPC486148
0.7011	Intermediate Similarity	NPC486126
0.697	Remote Similarity	NPC486140
0.69	Remote Similarity	NPC486133
0.6869	Remote Similarity	NPC120390
0.6602	Remote Similarity	NPC474423
0.6571	Remote Similarity	NPC486152
0.6458	Remote Similarity	NPC231518
0.6458	Remote Similarity	NPC488944
0.6444	Remote Similarity	NPC5311
0.6444	Remote Similarity	NPC77299
0.6444	Remote Similarity	NPC480906
0.6429	Remote Similarity	NPC329986
0.6429	Remote Similarity	NPC140092
0.6429	Remote Similarity	NPC486146
0.6421	Remote Similarity	NPC236973
0.6421	Remote Similarity	NPC32177
0.6421	Remote Similarity	NPC469756
0.6421	Remote Similarity	NPC275901
0.6374	Remote Similarity	NPC480914
0.6364	Remote Similarity	NPC486138
0.6364	Remote Similarity	NPC276838
0.6354	Remote Similarity	NPC188234
0.6263	Remote Similarity	NPC146857
0.6214	Remote Similarity	NPC475419
0.6186	Remote Similarity	NPC480910
0.6186	Remote Similarity	NPC32793
0.6186	Remote Similarity	NPC116075
0.6186	Remote Similarity	NPC480909
0.6154	Remote Similarity	NPC84987
0.6154	Remote Similarity	NPC486134
0.6154	Remote Similarity	NPC486141
0.6146	Remote Similarity	NPC30483
0.6146	Remote Similarity	NPC470897
0.6105	Remote Similarity	NPC480907
0.6095	Remote Similarity	NPC486150
0.6078	Remote Similarity	NPC479360
0.6078	Remote Similarity	NPC479359
0.6078	Remote Similarity	NPC488943
0.6078	Remote Similarity	NPC488942
0.602	Remote Similarity	NPC240070
0.6	Remote Similarity	NPC329675
0.6	Remote Similarity	NPC194716
0.5943	Remote Similarity	NPC329784
0.5918	Remote Similarity	NPC292467
0.5905	Remote Similarity	NPC74259
0.59	Remote Similarity	NPC125077
0.5859	Remote Similarity	NPC479353
0.5859	Remote Similarity	NPC479354
0.5851	Remote Similarity	NPC76572
0.5851	Remote Similarity	NPC193382
0.5849	Remote Similarity	NPC474908
0.5842	Remote Similarity	NPC469749
0.5806	Remote Similarity	NPC309034
0.58	Remote Similarity	NPC264336
0.58	Remote Similarity	NPC488941
0.58	Remote Similarity	NPC488940
0.5743	Remote Similarity	NPC59288
0.5741	Remote Similarity	NPC488945
0.5741	Remote Similarity	NPC488946
0.5714	Remote Similarity	NPC475590
0.57	Remote Similarity	NPC475556
0.57	Remote Similarity	NPC311706
0.5699	Remote Similarity	NPC99620
0.5631	Remote Similarity	NPC247190
0.5579	Remote Similarity	NPC469750
0.5524	Remote Similarity	NPC479357
0.5417	Remote Similarity	NPC157376
0.5417	Remote Similarity	NPC17896
0.5417	Remote Similarity	NPC469755
0.5417	Remote Similarity	NPC284406
0.5417	Remote Similarity	NPC197707
0.5417	Remote Similarity	NPC251866
0.5417	Remote Similarity	NPC142066
0.5417	Remote Similarity	NPC603972
0.5408	Remote Similarity	NPC305574
0.5368	Remote Similarity	NPC99728
0.5368	Remote Similarity	NPC87250
0.5368	Remote Similarity	NPC244402
0.5368	Remote Similarity	NPC50305
0.534	Remote Similarity	NPC610296
0.5312	Remote Similarity	NPC196429
0.5312	Remote Similarity	NPC486129
0.5204	Remote Similarity	NPC199428
0.5204	Remote Similarity	NPC243196
0.5204	Remote Similarity	NPC109448
0.5204	Remote Similarity	NPC310341
0.5185	Remote Similarity	NPC488938
0.5185	Remote Similarity	NPC488937
0.5152	Remote Similarity	NPC146456
0.5152	Remote Similarity	NPC250556
0.5146	Remote Similarity	NPC27363
0.5143	Remote Similarity	NPC208193
0.5135	Remote Similarity	NPC117445
0.5135	Remote Similarity	NPC308262
0.5102	Remote Similarity	NPC480915
0.51	Remote Similarity	NPC483822

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5718
0.1-0.2	3320
0.2-0.3	93
0.3-0.4	9
0.4-0.5	6
0.5-0.6	2
0.6-0.7	1
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
0.6458	Remote Similarity	NPD8033	Approved
0.5417	Remote Similarity	NPD7319	Approved
0.5152	Remote Similarity	NPD7507	Pre-clinical

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