NPASS Compound

Natural Product: NPC472670

Natural Product ID	NPC472670
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XDLKVPLICUIRQM-PHHWVVQSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581415
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 89 94 0 0 0 0 0 0 0 0999 V2000 0.7878 -3.7594 -1.2701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2134 -2.4274 -1.0899 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3082 -1.7332 -2.2643 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5434 -1.2593 -2.6095 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3014 -0.8354 -1.5180 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9890 -2.0385 -0.9504 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8122 -1.9099 0.4969 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7052 -0.9334 0.6858 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3876 -0.2998 -0.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3663 0.7513 -0.5959 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0905 0.1400 -1.0803 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3162 -0.6107 -2.3877 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1175 1.0251 -1.1723 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5196 1.4025 -2.5835 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3573 0.2905 -0.6175 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0004 -0.8803 0.0947 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4470 -2.1476 -0.2439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2049 -2.2243 -1.2427 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0910 -3.3478 0.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3004 -3.3040 1.5313 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9349 -4.5569 2.2772 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6168 -4.6575 0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1603 1.1252 0.3132 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2552 2.5920 -0.0243 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9541 3.2524 -0.2910 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9388 2.1583 -0.2707 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3283 2.8977 -0.2146 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2750 1.8228 0.4062 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6308 1.6358 1.5835 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0432 3.8665 0.7759 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3324 3.9828 0.9122 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9431 4.2228 -1.3950 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0304 3.2441 0.9586 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2714 3.8081 0.7184 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7378 3.7365 -0.4431 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0726 4.4895 1.7619 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8824 1.5587 -1.8195 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0610 -0.7606 2.0064 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0375 -1.5062 1.2271 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6405 -2.2802 2.1901 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7483 -1.5911 2.6495 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8008 -0.4696 1.9954 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7934 -0.3755 1.1305 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7351 -4.2545 -0.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4276 -4.2954 -1.9793 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2448 -3.7739 -1.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0175 -2.4670 -3.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0902 -0.1056 -1.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5488 -2.9940 -1.3325 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0938 -2.0128 -1.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4972 -2.9303 0.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1572 -0.6682 -0.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6328 0.0111 -3.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6856 -1.0851 -2.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1819 2.3750 -2.9275 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6520 1.4771 -2.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2585 0.6714 -3.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0272 -0.0593 -1.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9109 -2.3598 1.8632 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0364 -4.9681 1.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8155 -4.3107 3.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7439 -5.3141 2.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8773 -5.4637 0.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0296 -4.6331 -0.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4789 -4.9745 0.6954 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2227 0.7384 0.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8751 0.9716 1.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8628 2.6483 -0.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0868 1.7272 0.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7285 3.3572 -1.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2434 2.3163 0.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0776 2.0579 2.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6524 3.4508 1.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6281 5.0361 0.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7166 4.0465 -2.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2919 5.2123 -0.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9454 4.4507 -1.7797 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0879 5.5729 1.5203 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1361 4.1309 1.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6924 4.3095 2.7779 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0726 1.9112 -2.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4934 2.4425 -1.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5567 0.9858 -2.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9929 -0.9185 2.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4888 0.0573 2.6192 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4051 -1.6559 2.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3299 -3.2658 2.5532 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4079 -1.9820 3.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6086 0.4407 0.4760 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 2 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 19 22 1 0 15 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 27 30 1 0 30 31 1 0 25 32 1 6 24 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 10 37 1 6 8 38 1 0 7 39 1 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 1 0 12 3 1 0 26 13 1 0 43 39 2 0 9 5 1 0 28 10 1 0 31 25 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 6 5 48 1 6 6 49 1 0 6 50 1 0 7 51 1 1 11 52 1 1 12 53 1 0 12 54 1 0 14 55 1 0 14 56 1 0 14 57 1 0 15 58 1 6 20 59 1 0 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 24 68 1 6 26 69 1 1 27 70 1 6 28 71 1 1 29 72 1 0 31 73 1 0 31 74 1 0 32 75 1 0 32 76 1 0 32 77 1 0 36 78 1 0 36 79 1 0 36 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 38 84 1 0 38 85 1 0 38 86 1 0 40 87 1 0 41 88 1 0 43 89 1 0 M END

Standard InCHIKey	XDLKVPLICUIRQM-PHHWVVQSSA-N
Standard InCHI	InChI=1S/C34H46O9/c1-9-17(2)31(37)43-25-14-24(41-19(4)35)32(5)16-40-28-29(32)33(25,6)23-13-26(38-8)42-22-12-21(20-10-11-39-15-20)18(3)27(22)34(23,7)30(28)36/h9-11,15,21-26,28-30,36H,12-14,16H2,1-8H3/b17-9+/t21-,22-,23-,24-,25+,26-,28-,29+,30-,32-,33+,34-/m1/s1
SMILES	CO[C@@H]1O[C@@H]2C[C@H](C(=C2[C@]2([C@H](C1)[C@@]1(C)[C@@H](OC(=O)/C(=C/C)/C)C[C@H]([C@@]3([C@@H]1[C@H]([C@H]2O)OC3)C)OC(=O)C)C)C)c1ccoc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	598.31	Volume:	608.574 ? Van der Waals volume.
Dense:	0.983	LogP:	2.377 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.787 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.661 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	32.0
TPSA:	113.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.282	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.776	Fsp³:	0.706
MCE-18:	149.172 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.95	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? 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:	0.041	Promiscuous compounds:	0.405

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.195	MDCK Permeability:	-4.821
Pgp-inhibitor:	0.858	Pgp-substrate:	0.966
PAMPA:	0.733 ? 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):	0.0
20% Bioavailability (F20%):	0.418	30% Bioavailability (F30%):	0.335
50% Bioavailability (F50%):	0.791

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.999
Plasma Protein Binding (PPB):	86.132%	Volume Distribution (VD):	-0.195
Fu:	13.509% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.942
OATP1B3 inhibitor:	0.028	BCRP inhibitor:	0.006
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.822	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.338
CYP3A4-inhibitor:	0.935	CYP3A4-substrate:	0.772
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.602
HLM stability:	0.914 ? 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):

10.182

Half-life (T1/2):

1.451

ADMET: Toxicity

hERG Blockers:	0.122	hERG Blockers (10um):	0.131
Human Hepatotoxicity (H-HT):	0.794	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.667	Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.995	Skin Sensitization:	0.82
Carcinogencity:	0.513	Eye Corrosion:	0.0
Eye Irritation:	0.022	Respiratory Toxicity:	0.823
Drug-induced Neurotoxicity:	0.311	Ototoxicity:	0.862
Hematotoxicity:	0.383	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.274
A549 Cytotoxicity:	0.532	Hek293 Cytotoxicity:	0.127
BCF:	0.551 ? 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:	3.411 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.331 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.455 ? 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
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	whole plants	Wenshan, Yunnan Province, China	2012-Nov	PMID[25798528]
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9173	Munronia henryi	Species	Meliaceae	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	10
IC50	6

Activity Type	# Activity
Cell line	5
Organism	11

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	10000.0	nM	DrugMatrix in vitro pharmacology data
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[25462220]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PubChem BioAssay data set
NPT660	Cell line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[8863796]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	98.5	%	PMID[12502321]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	88.9	%	PMID[10091690]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	63.8	%	PMID[18494522]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	44.9	%	PMID[23489626]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	86.9	%	DOI[10.1007/s00044-012-0031-0]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	70.3	%	PMID[17125241]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	63.5	%	PMID[11312930]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.7	%	PMID[18293924]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	16.4	%	PMID[25007124]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	6.3	%	PMID[9651160]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	IC50	=	28.1	ug.mL-1	PMID[23993676]

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 NPC472670 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	12803
0.1-0.2	34828
0.2-0.3	2122
0.3-0.4	63
0.4-0.5	11
0.5-0.6	14
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC307781
1.0	High Similarity	NPC601577
0.9277	High Similarity	NPC264690
0.8023	Intermediate Similarity	NPC610307
0.7826	Intermediate Similarity	NPC11062
0.7753	Intermediate Similarity	NPC608851
0.7209	Intermediate Similarity	NPC601664
0.7174	Intermediate Similarity	NPC472671
0.7021	Intermediate Similarity	NPC472673
0.6421	Remote Similarity	NPC470792
0.6237	Remote Similarity	NPC29695
0.6224	Remote Similarity	NPC608643
0.6146	Remote Similarity	NPC308205
0.6129	Remote Similarity	NPC182427
0.6105	Remote Similarity	NPC610302
0.6082	Remote Similarity	NPC599832
0.596	Remote Similarity	NPC610301
0.5728	Remote Similarity	NPC608993
0.5612	Remote Similarity	NPC601608
0.5577	Remote Similarity	NPC27541
0.5521	Remote Similarity	NPC34421
0.5521	Remote Similarity	NPC237259
0.5408	Remote Similarity	NPC98206
0.5354	Remote Similarity	NPC609027
0.5333	Remote Similarity	NPC126984
0.53	Remote Similarity	NPC475066
0.5243	Remote Similarity	NPC214495
0.5243	Remote Similarity	NPC470119
0.5204	Remote Similarity	NPC604850
0.5098	Remote Similarity	NPC322546

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4426
0.1-0.2	4704
0.2-0.3	20
0.3-0.4	0
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