NPASS Compound

Natural Product: NPC176413

Natural Product ID	NPC176413
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SPACGDWQNCVTAS-YVCRAYHESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1829396
PubChem CID	56642787
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 91 96 0 0 0 0 0 0 0 0999 V2000 -3.3750 -0.6262 3.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2501 0.1374 2.9020 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0214 1.2914 3.3861 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4810 -0.3721 1.8706 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4202 0.4677 1.3820 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2408 -0.3756 0.2689 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7251 -1.6174 0.8891 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2207 -1.8225 0.9710 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0334 -0.9802 0.0543 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5492 0.4544 0.3644 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3065 0.4336 -0.4309 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8637 1.7798 -0.8827 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9377 2.8469 0.1905 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4289 1.8013 -1.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3674 0.7005 -1.3755 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8242 -0.5735 -0.7576 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9796 -1.2684 -0.3108 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4799 -2.3720 -0.9902 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8755 -2.7351 -2.0174 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6904 -3.0614 -0.4768 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4759 1.0991 -0.6049 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7494 0.9899 -1.1385 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9256 0.5337 -2.3059 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9051 1.3975 -0.3667 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7311 1.9090 0.8887 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8326 2.2945 1.6271 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0840 2.1542 1.0798 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2647 1.6386 -0.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1529 1.2616 -0.9029 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8546 2.1628 -1.8352 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5896 -0.2887 -1.6176 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6806 -1.0773 -1.3915 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9146 -0.5841 -2.1618 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4312 -2.4833 -1.8659 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4843 1.3971 -0.1025 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1330 2.3361 0.6611 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8782 2.3665 1.8897 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0935 3.2934 0.1337 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6998 4.2031 0.9688 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6174 5.1414 0.5580 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9652 5.1863 -0.7847 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3675 4.2801 -1.6439 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4439 3.3439 -1.1991 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1918 -2.8249 0.3738 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4636 -3.7544 1.1988 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5782 -3.4913 2.4209 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0092 -5.0045 0.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9839 -5.4997 -0.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 -6.7106 -0.5554 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0453 -6.9577 0.6669 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 -5.9698 1.4227 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8625 -1.1830 2.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1209 0.0541 3.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9640 -1.3050 4.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8796 1.3743 1.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2673 0.5744 2.2501 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4105 -1.6492 1.9892 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5851 -1.5447 2.0076 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4597 -2.9031 0.9060 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -1.1037 0.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3383 0.5227 1.4265 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0327 3.4335 0.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2343 2.4807 1.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6821 3.6632 -0.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9491 2.7664 -1.3137 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2959 1.9440 -2.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8035 0.3494 -2.3644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3816 -1.1322 -1.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4631 -2.2768 -0.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4558 -3.4657 0.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0571 -3.8273 -1.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7623 2.0328 1.3417 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7418 2.7049 2.6256 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9650 2.4513 1.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2654 1.5510 -0.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3235 0.8549 -1.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4637 2.7574 -2.5125 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8095 -1.0915 -1.7345 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0005 0.4966 -2.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7630 -0.9545 -3.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4018 -2.5945 -2.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0959 -2.7757 -2.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6293 -3.2548 -1.0920 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4408 4.1826 2.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0687 5.8404 1.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6811 5.9242 -1.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6598 4.3403 -2.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9982 2.6562 -1.8876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5515 -5.0605 -1.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8069 -7.3843 -1.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8922 -5.8996 2.4720 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 1 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 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 12 30 1 6 11 31 1 6 31 32 1 0 32 33 1 0 32 34 1 0 10 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 7 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 1 0 16 6 1 0 29 24 1 0 43 38 1 0 51 47 2 0 11 6 1 0 32 9 1 0 1 52 1 0 1 53 1 0 1 54 1 0 5 55 1 0 5 56 1 0 7 57 1 1 8 58 1 0 8 59 1 0 9 60 1 6 10 61 1 1 13 62 1 0 13 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 15 67 1 6 16 68 1 6 20 69 1 0 20 70 1 0 20 71 1 0 25 72 1 0 26 73 1 0 27 74 1 0 28 75 1 0 29 76 1 0 30 77 1 0 33 78 1 0 33 79 1 0 33 80 1 0 34 81 1 0 34 82 1 0 34 83 1 0 39 84 1 0 40 85 1 0 41 86 1 0 42 87 1 0 43 88 1 0 48 89 1 0 49 90 1 0 51 91 1 0 M END

Standard InCHIKey	SPACGDWQNCVTAS-YVCRAYHESA-N
Standard InCHI	InChI=1S/C38H40O13/c1-22(39)46-21-37-29(49-34(43)26-16-17-45-20-26)18-27-30(50-33(42)25-14-10-7-11-15-25)38(37,51-35(27,3)4)36(5,44)19-28(31(37)47-23(2)40)48-32(41)24-12-8-6-9-13-24/h6-17,20,27-31,44H,18-19,21H2,1-5H3/t27-,28+,29+,30-,31+,36+,37-,38+/m1/s1
SMILES	CC(=O)OC[C@@]12[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)(C[C@@H]([C@@H]1OC(=O)C)OC(=O)c1ccccc1)O)OC3(C)C)OC(=O)c1ccccc1)OC(=O)c1ccoc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	704.25	Volume:	694.464 ? Van der Waals volume.
Dense:	1.014	LogP:	3.478 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.271 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.023 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	36.0
TPSA:	174.1 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.245	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.014	Fsp³:	0.447
MCE-18:	189.2 ? 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:	0.538	Fluc inhibitor:	0.02 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.343 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.053	Promiscuous compounds:	0.026

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.524	MDCK Permeability:	-4.939
Pgp-inhibitor:	0.999	Pgp-substrate:	0.176
PAMPA:	0.225 ? 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%):	0.02	30% Bioavailability (F30%):	0.167
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.768	MRP1:	1.0
Plasma Protein Binding (PPB):	86.217%	Volume Distribution (VD):	-0.442
Fu:	14.19% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.83	BCRP inhibitor:	0.008
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.722
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.064	CYP3A4-substrate:	0.464
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

1.514

Half-life (T1/2):

1.287

ADMET: Toxicity

hERG Blockers:	0.061	hERG Blockers (10um):	0.551
Human Hepatotoxicity (H-HT):	0.022	Drug-induced Liver Injury (DILI):	0.96
AMES Toxicity:	0.794	Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.685	Skin Sensitization:	0.99
Carcinogencity:	0.956	Eye Corrosion:	0.0
Eye Irritation:	0.435	Respiratory Toxicity:	0.071
Drug-induced Neurotoxicity:	0.648	Ototoxicity:	0.167
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.577
Genotoxicity:	0.615	RPMI-8226 Immunitoxicity:	0.07
A549 Cytotoxicity:	0.391	Hek293 Cytotoxicity:	0.694
BCF:	0.684 ? 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:	3.865 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.216 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.9 ? 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
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26437	Maytenus jelskii	Species	Celastraceae	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	1
Ki	1
Imax	1
Ratio IC50	6
Activity	2

Activity Type	# Activity
Cell line	2
Individual protein	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	70.0	%	PMID[19128055]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	340.0	nM	PMID[25621853]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Imax	>	90.0	%	PMID[21856049]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	7.82	n.a.	PMID[18611050]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	14.07	n.a.	PMID[26034885]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	17.11	n.a.	PMID[12502328]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	10.34	n.a.	PMID[18640035]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	14.26	n.a.	PMID[12762808]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	51.67	n.a.	PMID[25084548]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	82.14	%	PMID[16872140]
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	84.33	%	PMID[4851320]

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 NPC176413 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	12581
0.1-0.2	34772
0.2-0.3	1958
0.3-0.4	364
0.4-0.5	114
0.5-0.6	43
0.6-0.7	9
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC294512
0.8987	High Similarity	NPC483885
0.8987	High Similarity	NPC479045
0.8442	Intermediate Similarity	NPC6815
0.8125	Intermediate Similarity	NPC56953
0.7975	Intermediate Similarity	NPC479049
0.7922	Intermediate Similarity	NPC70716
0.7922	Intermediate Similarity	NPC95265
0.7901	Intermediate Similarity	NPC479041
0.7468	Intermediate Similarity	NPC97667
0.7356	Intermediate Similarity	NPC483868
0.7349	Intermediate Similarity	NPC479048
0.7073	Intermediate Similarity	NPC479042
0.686	Remote Similarity	NPC610134
0.6782	Remote Similarity	NPC75600
0.6782	Remote Similarity	NPC483884
0.6265	Remote Similarity	NPC171207
0.6235	Remote Similarity	NPC96903
0.6222	Remote Similarity	NPC483870
0.6118	Remote Similarity	NPC472569
0.6087	Remote Similarity	NPC483869
0.6024	Remote Similarity	NPC191082
0.5977	Remote Similarity	NPC472568
0.593	Remote Similarity	NPC472570
0.5909	Remote Similarity	NPC294803
0.587	Remote Similarity	NPC10904
0.587	Remote Similarity	NPC148896
0.5862	Remote Similarity	NPC127720
0.5843	Remote Similarity	NPC481488
0.5833	Remote Similarity	NPC4341
0.5747	Remote Similarity	NPC11685
0.5747	Remote Similarity	NPC16912
0.573	Remote Similarity	NPC481064
0.573	Remote Similarity	NPC481062
0.573	Remote Similarity	NPC481058
0.573	Remote Similarity	NPC481060
0.5699	Remote Similarity	NPC180668
0.5647	Remote Similarity	NPC479047
0.5647	Remote Similarity	NPC291638
0.5618	Remote Similarity	NPC471102
0.5612	Remote Similarity	NPC471013
0.5581	Remote Similarity	NPC67777
0.5568	Remote Similarity	NPC57628
0.5556	Remote Similarity	NPC481489
0.5556	Remote Similarity	NPC609309
0.5532	Remote Similarity	NPC127026
0.5532	Remote Similarity	NPC483890
0.5495	Remote Similarity	NPC271460
0.5484	Remote Similarity	NPC610927
0.5402	Remote Similarity	NPC139067
0.5402	Remote Similarity	NPC177340
0.5333	Remote Similarity	NPC184747
0.5281	Remote Similarity	NPC479044
0.5275	Remote Similarity	NPC147340
0.5275	Remote Similarity	NPC282239
0.5248	Remote Similarity	NPC471980
0.5227	Remote Similarity	NPC270590
0.5227	Remote Similarity	NPC43241
0.5158	Remote Similarity	NPC611111
0.5111	Remote Similarity	NPC41481
0.5111	Remote Similarity	NPC481061
0.5109	Remote Similarity	NPC36021
0.5104	Remote Similarity	NPC301368
0.5104	Remote Similarity	NPC84815
0.5051	Remote Similarity	NPC30171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC176413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2692
0.1-0.2	6308
0.2-0.3	149
0.3-0.4	1
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