NPASS Compound

Natural Product: NPC488079

Natural Product ID	NPC488079
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RJEVYKCNHVUXCJ-XPUCJSRNSA-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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 102107 0 0 0 0 0 0 0 0999 V2000 11.9922 1.9623 3.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8757 1.2363 2.2125 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5824 0.1980 1.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2849 -0.2517 1.2474 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9407 -1.2958 0.4148 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9269 -1.9171 -0.3180 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2207 -1.4800 -0.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5670 -0.4307 0.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8609 0.0252 0.7756 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5617 -1.7724 0.2892 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5406 -1.2909 0.9714 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1948 -1.8197 0.7879 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9854 -2.7621 -0.0535 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1068 -1.3613 1.4758 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7752 -1.8156 1.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2601 -1.5893 -0.0777 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2205 -0.0684 -0.3092 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9669 0.0649 -1.7964 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0976 -1.0206 -2.3242 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2535 -1.7276 -1.2707 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2537 -0.8731 -0.9204 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1050 -0.8406 -1.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8005 0.2882 -0.5631 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1661 0.4237 -0.6506 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9357 -0.5596 -1.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2848 -1.6692 -1.7073 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8922 -1.8030 -1.6149 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3282 -2.9806 -2.1271 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4068 -4.0896 -1.2000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0665 -2.6692 -2.2942 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2968 -0.4328 -1.3224 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0245 -1.3232 -1.8498 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8650 0.7572 -0.7948 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0806 1.7046 -0.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6360 2.9447 0.3098 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7723 3.6188 1.1947 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0953 4.8154 1.7292 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2874 5.4254 1.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1427 4.7523 0.5473 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8108 3.5230 -0.0018 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3235 5.3732 0.2547 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2597 4.8056 -0.6245 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6559 6.6616 1.9615 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7853 1.4825 -0.1954 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2455 0.8021 -0.9255 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1228 0.1430 0.0058 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2263 1.0201 0.4497 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5037 0.3531 0.8296 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7925 -0.9536 0.1815 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4536 -1.7152 0.1764 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6260 -3.0966 -0.3654 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4559 -3.8713 0.4802 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6469 -0.9826 -0.6691 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1394 -0.7911 -1.1719 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5266 1.2895 0.6313 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7948 1.7381 1.6000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9796 -2.0391 -0.1341 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8992 -1.9932 -2.9144 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4133 1.3180 -2.0434 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3894 0.5540 0.0367 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4228 2.9708 3.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0302 2.1575 2.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7068 1.4966 3.9531 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5371 0.2633 1.8397 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6316 -2.7340 -0.9636 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9890 -1.9694 -0.7719 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2077 0.2035 1.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3388 -2.5865 -0.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6845 -0.4954 1.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1467 -1.1689 1.9982 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6236 -2.8515 1.6813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9397 -1.9844 -0.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3358 0.2704 0.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9795 0.0715 -2.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4459 -0.6172 -3.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9131 -2.6863 -1.6949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1944 1.0586 -0.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3469 -4.6395 -1.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4992 -4.6962 -1.3914 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2973 -3.7069 -0.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6024 -3.2783 -1.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8003 3.1786 1.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 5.3199 2.4208 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4674 3.0148 -0.6900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8541 5.6452 -1.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9346 4.0931 -0.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7510 4.3391 -1.5168 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9793 6.6374 2.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5093 -0.2033 0.8794 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4516 1.7974 -0.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4953 0.1696 1.9350 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5535 -1.5083 0.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0628 -1.7905 1.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6459 -3.6100 -0.3249 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9926 -3.1238 -1.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6800 -4.6904 -0.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3165 -0.6462 -1.7200 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4087 0.9054 0.8954 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3179 1.0920 2.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3980 -2.8561 -2.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0414 1.9240 -2.5433 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5964 1.2402 -0.6706 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 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 26 30 1 0 25 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 1 0 38 43 1 0 34 44 1 0 33 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 20 57 1 0 19 58 1 0 18 59 1 0 17 60 1 0 8 3 1 0 57 16 1 0 27 22 1 0 40 35 1 0 53 46 1 0 44 24 1 0 1 61 1 0 1 62 1 0 1 63 1 0 4 64 1 0 6 65 1 0 7 66 1 0 9 67 1 0 10 68 1 0 11 69 1 0 15 70 1 0 15 71 1 0 16 72 1 6 17 73 1 1 18 74 1 6 19 75 1 6 20 76 1 6 23 77 1 0 29 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 36 82 1 0 37 83 1 0 40 84 1 0 42 85 1 0 42 86 1 0 42 87 1 0 43 88 1 0 46 89 1 1 47 90 1 6 48 91 1 1 49 92 1 1 50 93 1 1 51 94 1 0 51 95 1 0 52 96 1 0 54 97 1 0 55 98 1 0 56 99 1 0 58100 1 0 59101 1 0 60102 1 0 M END

Standard InCHIKey	RJEVYKCNHVUXCJ-XPUCJSRNSA-N
Standard InCHI	InChI=1S/C39H42O21/c1-52-19-10-15(4-7-17(19)41)5-9-25(43)55-14-24-28(45)32(49)33(50)38(59-24)57-22-12-21-26(29(46)36(22)54-3)30(47)37(35(56-21)16-6-8-18(42)20(11-16)53-2)60-39-34(51)31(48)27(44)23(13-40)58-39/h4-12,23-24,27-28,31-34,38-42,44-46,48-51H,13-14H2,1-3H3/b9-5+/t23-,24-,27+,28-,31+,32+,33-,34-,38-,39+/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc3c(c(c2OC)O)c(=O)c(c(c2ccc(c(c2)OC)O)o3)O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	846.22	Volume:	782.082 ? Van der Waals volume.
Dense:	1.082	LogP:	1.188 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.452 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.824 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	38.0
TPSA:	323.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.058	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.197	Fsp³:	0.385
MCE-18:	144.926 ? 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:	0
Colloidal aggregators:	0.716	Fluc inhibitor:	0.369 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.796 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.67 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.036	Promiscuous compounds:	0.457

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.217	MDCK Permeability:	-5.499
Pgp-inhibitor:	0.0	Pgp-substrate:	0.095
PAMPA:	0.932 ? 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):	0.994
20% Bioavailability (F20%):	0.953	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.045
Plasma Protein Binding (PPB):	84.021%	Volume Distribution (VD):	-0.107
Fu:	13.366% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.34
BSEP inhibitor:	0.036

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:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.084 ? 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):

1.041

Half-life (T1/2):

4.389

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.101
Human Hepatotoxicity (H-HT):	0.673	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.965	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.033	Skin Sensitization:	1.0
Carcinogencity:	0.063	Eye Corrosion:	0.0
Eye Irritation:	0.018	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.939
Hematotoxicity:	0.267	Drug-induced Nephrotoxicity:	0.93
Genotoxicity:	0.59	RPMI-8226 Immunitoxicity:	0.462
A549 Cytotoxicity:	0.954	Hek293 Cytotoxicity:	0.732
BCF:	0.601 ? 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:	3.245 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.908 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.071 ? 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
NPO40820	Corispermum marschallii	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[30109803]

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	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
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	6000.0	nM	PMID[30109803]
NPT2740	Cell line	Neutrophils	n.a.	IC50	=	20700.0	nM	PMID[30109803]

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 NPC488079 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	18033
0.1-0.2	27524
0.2-0.3	3033
0.3-0.4	916
0.4-0.5	270
0.5-0.6	56
0.6-0.7	20
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
0.901	High Similarity	NPC488078
0.7396	Intermediate Similarity	NPC488072
0.7264	Intermediate Similarity	NPC470416
0.6972	Remote Similarity	NPC217520
0.6847	Remote Similarity	NPC139571
0.6574	Remote Similarity	NPC36138
0.6283	Remote Similarity	NPC477895
0.6238	Remote Similarity	NPC488071
0.6176	Remote Similarity	NPC101026
0.6176	Remote Similarity	NPC488077
0.6154	Remote Similarity	NPC295625
0.614	Remote Similarity	NPC480796
0.614	Remote Similarity	NPC472993
0.6134	Remote Similarity	NPC470720
0.6066	Remote Similarity	NPC25946
0.605	Remote Similarity	NPC470717
0.604	Remote Similarity	NPC24043
0.604	Remote Similarity	NPC603655
0.6036	Remote Similarity	NPC85751
0.6036	Remote Similarity	NPC19240
0.6019	Remote Similarity	NPC21666
0.6016	Remote Similarity	NPC21359
0.6016	Remote Similarity	NPC460984
0.5963	Remote Similarity	NPC153755
0.5962	Remote Similarity	NPC602805
0.5929	Remote Similarity	NPC223426
0.5917	Remote Similarity	NPC470719
0.5877	Remote Similarity	NPC214621
0.5877	Remote Similarity	NPC34267
0.5877	Remote Similarity	NPC81042
0.5833	Remote Similarity	NPC470713
0.5755	Remote Similarity	NPC203050
0.5755	Remote Similarity	NPC225434
0.5673	Remote Similarity	NPC471405
0.5556	Remote Similarity	NPC476865
0.5536	Remote Similarity	NPC488073
0.5514	Remote Similarity	NPC206123
0.55	Remote Similarity	NPC277532
0.5492	Remote Similarity	NPC474093
0.5492	Remote Similarity	NPC104910
0.5421	Remote Similarity	NPC476869
0.5391	Remote Similarity	NPC270675
0.5391	Remote Similarity	NPC195685
0.537	Remote Similarity	NPC476868
0.5345	Remote Similarity	NPC80068
0.5345	Remote Similarity	NPC476472
0.5345	Remote Similarity	NPC294815
0.5345	Remote Similarity	NPC16194
0.5339	Remote Similarity	NPC603856
0.5328	Remote Similarity	NPC470716
0.5294	Remote Similarity	NPC599948
0.5289	Remote Similarity	NPC470715
0.5289	Remote Similarity	NPC164704
0.5283	Remote Similarity	NPC488080
0.5283	Remote Similarity	NPC169977
0.5254	Remote Similarity	NPC470450
0.5234	Remote Similarity	NPC42773
0.5234	Remote Similarity	NPC45522
0.5234	Remote Similarity	NPC117260
0.5221	Remote Similarity	NPC233994
0.5217	Remote Similarity	NPC488364
0.5182	Remote Similarity	NPC469931
0.5182	Remote Similarity	NPC48773
0.5167	Remote Similarity	NPC121703
0.514	Remote Similarity	NPC27640
0.514	Remote Similarity	NPC105025
0.5135	Remote Similarity	NPC211594
0.5133	Remote Similarity	NPC11411
0.5126	Remote Similarity	NPC472994
0.5124	Remote Similarity	NPC473072
0.5116	Remote Similarity	NPC480472
0.5109	Remote Similarity	NPC475179
0.5093	Remote Similarity	NPC201292
0.5086	Remote Similarity	NPC211532
0.5086	Remote Similarity	NPC483415
0.5085	Remote Similarity	NPC477629
0.5044	Remote Similarity	NPC609888
0.5043	Remote Similarity	NPC483416
0.5041	Remote Similarity	NPC470712

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4599
0.1-0.2	4492
0.2-0.3	46
0.3-0.4	9
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