NPASS Compound

Natural Product: NPC475382

Natural Product ID	NPC475382
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Acacetin 7-O-Alpha-L-Rhamnopyranosyl-(1->6)-[Alpha-L-Rhamnopyranosyl](1->2)-Beta-D-Glucopyranoside
IUPAC Name	7-[(2R,3R,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504601
PubChem CID	44575350
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 92 97 0 0 0 0 0 0 0 0999 V2000 -5.3606 4.4109 -1.9507 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7330 3.0375 -2.1971 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8353 2.0196 -2.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2776 0.6289 -2.0150 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7742 0.7497 -2.3080 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2541 1.5852 -1.1280 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6985 2.8966 -1.3000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8292 1.0709 -0.0085 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0641 0.6171 0.9887 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3395 1.4507 2.2321 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1151 0.6574 3.2588 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0802 -0.3067 2.6264 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5148 -1.1650 1.7079 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1969 -0.8154 1.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7006 -1.7390 0.5083 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7387 -2.5145 1.1067 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0375 -3.9984 1.0136 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9267 -4.6224 0.1828 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4125 -4.2997 0.8530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4558 -2.8869 1.3066 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4988 -2.1924 0.5058 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -2.2942 1.3055 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3845 -1.6779 0.2933 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9002 -1.6295 -0.9956 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -1.0118 -2.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8094 -0.4254 -1.7027 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3417 -0.4450 -0.4236 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6215 -1.0743 0.5693 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5149 0.1253 -0.1558 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2400 0.7338 -1.0614 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7388 0.7695 -2.3445 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5372 0.2029 -2.6882 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0616 0.2244 -3.8542 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5190 1.3358 -0.6803 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3286 1.9517 -1.5802 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5477 2.5396 -1.2202 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9637 2.5048 0.0899 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1450 1.8787 1.0126 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9323 1.2968 0.6407 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1712 3.0724 0.5271 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0561 3.7264 -0.3426 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1349 -0.9418 -3.3270 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7532 -5.2017 1.8412 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0333 -5.9834 0.0380 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8880 -4.5255 2.3191 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6558 -1.1729 3.7546 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2534 -0.4037 4.7411 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8858 1.5560 4.0092 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1665 1.8930 2.8365 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2587 -0.5244 -2.3183 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9196 -0.2464 -2.8515 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6801 2.1197 -3.1387 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9552 4.4300 -1.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0083 4.7367 -2.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5286 5.1608 -1.8768 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4107 3.0596 -3.2685 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4185 2.2792 -1.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3424 0.2732 -0.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5656 1.2072 -3.2742 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1780 1.5999 -1.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9932 0.7629 0.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9376 2.3665 1.9848 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4431 0.0813 3.9337 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9149 0.2514 2.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6543 -0.9343 2.3579 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1908 2.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0193 -4.2172 0.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9214 -4.0891 -0.8037 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1939 -4.4055 0.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0452 -2.8007 2.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9355 -2.0998 -1.2470 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0265 -1.0994 1.5941 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3067 1.2605 -3.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0780 2.0227 -2.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1772 3.0244 -1.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4756 1.8515 2.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2915 0.8097 1.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6835 4.4582 0.2117 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4662 4.3099 -1.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6817 3.0353 -0.9289 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7010 -0.0713 -3.6106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5969 -5.6785 1.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8758 -6.1814 -0.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5209 -5.4469 2.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8455 -1.8278 4.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4225 -1.8481 3.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2225 -0.5712 4.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7443 1.6695 3.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6297 2.4326 2.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9446 -1.2219 -2.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7209 -0.5884 -2.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9739 1.2324 -3.4701 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 0 20 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 30 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 40 41 1 0 25 42 1 0 19 43 1 0 18 44 1 0 17 45 1 0 12 46 1 0 46 47 1 0 11 48 1 0 10 49 1 0 5 50 1 0 4 51 1 0 3 52 1 0 7 2 1 0 14 9 1 0 21 16 1 0 28 23 1 0 32 26 1 0 39 34 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 0 3 57 1 0 4 58 1 0 5 59 1 0 6 60 1 0 9 61 1 0 10 62 1 0 11 63 1 0 12 64 1 0 14 65 1 0 16 66 1 0 17 67 1 0 18 68 1 0 19 69 1 0 20 70 1 0 24 71 1 0 28 72 1 0 31 73 1 0 35 74 1 0 36 75 1 0 38 76 1 0 39 77 1 0 41 78 1 0 41 79 1 0 41 80 1 0 42 81 1 0 43 82 1 0 44 83 1 0 45 84 1 0 46 85 1 0 46 86 1 0 47 87 1 0 48 88 1 0 49 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 M END

Standard InCHIKey	LPFFEQMPQWBGLC-CAMRQUDDSA-N
Standard InCHI	InChI=1S/C33H40O19/c1-11-21(37)23(39)26(42)30(46-11)50-29-25(41)22(38)19(10-34)49-33(29)52-32-28(44)24(40)27(43)31(51-32)47-14-7-15(35)20-16(36)9-17(48-18(20)8-14)12-3-5-13(45-2)6-4-12/h3-9,11,19,21-35,37-44H,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25-,26+,27+,28+,29+,30-,31+,32-,33-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(C(O3)OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC=C(C=C6)OC)O)O)O)O)CO)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.22	Volume:	673.908 ? Van der Waals volume.
Dense:	1.098	LogP:	-0.793 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.284 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.784 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	297.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.211	Fsp³:	0.545
MCE-18:	147.118 ? 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:	0.169	Fluc inhibitor:	0.068 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.959 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.975 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.48	Promiscuous compounds:	0.29

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.559	MDCK Permeability:	-5.031
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	1.0
20% Bioavailability (F20%):	0.98	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.977
Plasma Protein Binding (PPB):	72.77%	Volume Distribution (VD):	-0.286
Fu:	26.601% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.963	BCRP inhibitor:	0.547
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.04	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:	0.79
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):

0.558

Half-life (T1/2):

4.378

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.33
Human Hepatotoxicity (H-HT):	0.39	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.854	Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.245	Skin Sensitization:	0.018
Carcinogencity:	0.182	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.12	Ototoxicity:	0.994
Hematotoxicity:	0.02	Drug-induced Nephrotoxicity:	0.047
Genotoxicity:	0.474	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.062	Hek293 Cytotoxicity:	0.874
BCF:	0.405 ? 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:	2.967 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.088 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.746 ? 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
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	bought from a drugstore in Beijing	n.a.	PMID[10514305]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[14738377]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	n.a.	n.a.	PMID[21524582]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	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
Inhibition	2

Activity Type	# Activity
Individual protein	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT183	Individual protein	Arachidonate 5-lipoxygenase	Rattus norvegicus	Inhibition	=	0.0	%	PMID[19203247]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Inhibition	=	0.0	%	PMID[17480098]

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 NPC475382 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	21708
0.1-0.2	23546
0.2-0.3	3685
0.3-0.4	604
0.4-0.5	220
0.5-0.6	56
0.6-0.7	27
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
0.7551	Intermediate Similarity	NPC311850
0.7294	Intermediate Similarity	NPC95090
0.7294	Intermediate Similarity	NPC27408
0.7174	Intermediate Similarity	NPC22062
0.7174	Intermediate Similarity	NPC65003
0.7174	Intermediate Similarity	NPC473634
0.7174	Intermediate Similarity	NPC138811
0.699	Remote Similarity	NPC68592
0.6915	Remote Similarity	NPC115674
0.6907	Remote Similarity	NPC195257
0.6762	Remote Similarity	NPC198199
0.6634	Remote Similarity	NPC11468
0.6606	Remote Similarity	NPC262222
0.6593	Remote Similarity	NPC80188
0.6444	Remote Similarity	NPC181712
0.6442	Remote Similarity	NPC473644
0.6413	Remote Similarity	NPC22832
0.6413	Remote Similarity	NPC243930
0.6364	Remote Similarity	NPC209296
0.6321	Remote Similarity	NPC488083
0.6316	Remote Similarity	NPC8856
0.6296	Remote Similarity	NPC298666
0.6292	Remote Similarity	NPC331652
0.6273	Remote Similarity	NPC120952
0.6222	Remote Similarity	NPC39360
0.6222	Remote Similarity	NPC29763
0.6222	Remote Similarity	NPC210003
0.6186	Remote Similarity	NPC44931
0.617	Remote Similarity	NPC607707
0.6061	Remote Similarity	NPC257566
0.6044	Remote Similarity	NPC19709
0.604	Remote Similarity	NPC473623
0.6	Remote Similarity	NPC311830
0.6	Remote Similarity	NPC220169
0.598	Remote Similarity	NPC488089
0.5978	Remote Similarity	NPC189142
0.5978	Remote Similarity	NPC77660
0.5962	Remote Similarity	NPC135358
0.596	Remote Similarity	NPC210073
0.5934	Remote Similarity	NPC473043
0.5914	Remote Similarity	NPC186807
0.5909	Remote Similarity	NPC488086
0.59	Remote Similarity	NPC204693
0.5882	Remote Similarity	NPC32641
0.5882	Remote Similarity	NPC256188
0.587	Remote Similarity	NPC58053
0.587	Remote Similarity	NPC261866
0.5842	Remote Similarity	NPC46202
0.5842	Remote Similarity	NPC240306
0.5729	Remote Similarity	NPC601144
0.5728	Remote Similarity	NPC35119
0.5727	Remote Similarity	NPC488087
0.5699	Remote Similarity	NPC143851
0.5684	Remote Similarity	NPC27942
0.5567	Remote Similarity	NPC608742
0.5437	Remote Similarity	NPC122809
0.5421	Remote Similarity	NPC101636
0.5405	Remote Similarity	NPC480441
0.5405	Remote Similarity	NPC25523
0.537	Remote Similarity	NPC253685
0.5368	Remote Similarity	NPC289667
0.5347	Remote Similarity	NPC251417
0.5347	Remote Similarity	NPC239549
0.5321	Remote Similarity	NPC14187
0.5306	Remote Similarity	NPC611303
0.5301	Remote Similarity	NPC29353
0.53	Remote Similarity	NPC190003
0.5278	Remote Similarity	NPC298171
0.5234	Remote Similarity	NPC479766
0.52	Remote Similarity	NPC88023
0.52	Remote Similarity	NPC116458
0.52	Remote Similarity	NPC246943
0.52	Remote Similarity	NPC309025
0.52	Remote Similarity	NPC605784
0.5182	Remote Similarity	NPC244875
0.5155	Remote Similarity	NPC93337
0.5152	Remote Similarity	NPC609451
0.514	Remote Similarity	NPC124155
0.513	Remote Similarity	NPC488088
0.5102	Remote Similarity	NPC84362
0.5102	Remote Similarity	NPC105025
0.5102	Remote Similarity	NPC610763
0.51	Remote Similarity	NPC486578
0.51	Remote Similarity	NPC605067
0.5098	Remote Similarity	NPC211594
0.5094	Remote Similarity	NPC64051
0.5094	Remote Similarity	NPC606547
0.5093	Remote Similarity	NPC142142
0.5047	Remote Similarity	NPC65711
0.5046	Remote Similarity	NPC479765

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5397
0.1-0.2	3670
0.2-0.3	72
0.3-0.4	6
0.4-0.5	3
0.5-0.6	0
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
0.6364	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