NPASS Compound

Natural Product: NPC473506

Natural Product ID	NPC473506
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XWKAQZKNPBZWNK-RMJHFGBWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444119
PubChem CID	44575771
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids 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 103108 0 0 0 0 0 0 0 0999 V2000 6.2822 1.9273 -0.3211 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7779 1.5467 -0.2467 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0459 2.6636 -1.0477 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8186 2.0239 -1.6472 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0963 1.1263 -2.5202 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5044 2.2156 -1.4043 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6320 1.1997 -2.0527 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8021 1.5278 -2.0900 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6173 0.2080 -1.9487 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5300 -0.2270 -0.4553 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4479 -1.3751 -0.1129 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7993 -2.4359 0.7650 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4586 -2.8927 0.3774 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2817 -2.1664 -1.0419 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1347 -0.7924 -0.4936 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7857 0.1955 -0.9331 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8062 1.2004 0.3071 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0570 -0.3161 -1.0585 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5003 -1.0799 0.6681 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7825 -2.3657 0.9172 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2318 -2.1424 2.3405 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0221 -0.9932 2.3673 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.6530 1.9460 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9326 -1.4302 1.4294 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9016 0.6926 2.0465 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4301 1.5569 1.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9102 2.7248 1.7906 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8852 3.0358 3.0769 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3377 2.1307 3.9478 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8589 0.9859 3.4328 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8608 -3.1906 0.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7267 -2.7321 -1.7559 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5552 -3.4963 -2.9247 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6368 -3.6502 -3.3139 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7212 -4.0788 -3.6436 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6675 -3.5880 0.5817 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3365 -4.1844 1.6317 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1619 -3.6813 2.7793 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2230 -5.3454 1.5043 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5649 -0.9047 0.6742 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8673 -0.9787 0.2750 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1206 -1.4868 -0.8462 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0198 -0.4975 1.0772 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8663 0.9365 0.1438 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0622 1.2662 1.4466 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8987 0.3354 2.2632 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4436 2.6173 1.9180 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5997 2.8682 3.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 4.1236 3.7354 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1783 5.1550 2.8518 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0230 4.9064 1.5107 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6564 3.6429 1.0328 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9232 0.3918 -2.3699 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4376 -0.2664 -3.4925 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6108 -1.0356 -4.0782 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8172 -0.0757 -3.9448 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1136 1.9917 -3.3918 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9417 3.1964 -2.1252 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5526 1.8469 -1.3701 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4471 2.9327 0.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8072 1.1595 0.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6680 0.5906 -0.7306 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7945 3.4335 -0.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0326 0.9286 -3.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0769 2.2577 -1.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1251 -0.4934 -2.6113 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9221 -1.7548 -1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8527 -2.2432 1.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4111 -3.9638 0.0495 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2156 -2.4183 -1.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1925 2.0814 0.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8593 1.5080 0.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5709 0.7271 1.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1405 -1.0492 -1.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8279 -3.0054 2.7485 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4087 -2.0028 3.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 3.9800 3.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2912 2.3173 5.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4215 0.1557 4.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4604 -4.1738 -0.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5646 -2.8341 -0.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5034 -3.7124 1.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5263 -3.3517 -3.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1487 -4.9574 -3.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3634 -4.4078 -4.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1237 -5.1574 2.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7180 -6.2515 1.8776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5705 -5.4333 0.4514 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5741 -1.4061 1.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6948 0.1244 1.9302 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7367 0.0943 0.4701 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4463 2.1035 4.0056 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0782 4.2860 4.7980 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4640 6.1507 3.1814 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1986 5.7411 0.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5626 3.5423 -0.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4781 -0.8260 -3.4841 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1785 0.9542 -3.7378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8940 -0.2267 -5.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2972 2.3150 -3.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2502 2.4060 -2.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3462 3.9874 -2.6588 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7880 3.7149 -1.6658 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 2 0 4 6 1 0 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 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 15 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 20 31 1 0 14 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 12 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 11 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 10 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 9 53 1 0 53 54 1 0 54 55 2 0 54 56 1 0 8 57 1 0 3 58 1 0 26 2 1 0 16 7 1 0 15 10 1 0 20 13 1 0 30 25 1 0 52 47 1 0 1 59 1 0 1 60 1 0 1 61 1 0 2 62 1 0 3 63 1 0 7 64 1 0 8 65 1 0 9 66 1 0 11 67 1 0 12 68 1 0 13 69 1 0 14 70 1 0 17 71 1 0 17 72 1 0 17 73 1 0 18 74 1 0 21 75 1 0 21 76 1 0 28 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 31 81 1 0 31 82 1 0 35 83 1 0 35 84 1 0 35 85 1 0 39 86 1 0 39 87 1 0 39 88 1 0 43 89 1 0 43 90 1 0 43 91 1 0 48 92 1 0 49 93 1 0 50 94 1 0 51 95 1 0 52 96 1 0 56 97 1 0 56 98 1 0 56 99 1 0 57100 1 0 58101 1 0 58102 1 0 58103 1 0 M END

Standard InCHIKey	XWKAQZKNPBZWNK-RMJHFGBWSA-N
Standard InCHI	InChI=1S/C40H45NO17/c1-18-19(2)34(47)56-31-28(46)32(54-22(5)44)39(57-35(48)24-13-10-9-11-14-24)33(55-23(6)45)29(52-20(3)42)26-30(53-21(4)43)40(39,38(31,8)50)58-37(26,7)17-51-36(49)25-15-12-16-41-27(18)25/h9-16,18-19,26,28-33,46,50H,17H2,1-8H3/t18?,19?,26-,28+,29-,30-,31+,32+,33-,37+,38+,39-,40+/m1/s1
SMILES	CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C6=CC=CC=C6)OC(=O)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	811.27	Volume:	775.214 ? Van der Waals volume.
Dense:	1.047	LogP:	1.242 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.61 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.471 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	42.0
TPSA:	246.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.31	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.577	Fsp³:	0.55
MCE-18:	218.129 ? 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:	0.121	Fluc inhibitor:	0.0 ? 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:	0.138 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.009	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.473	MDCK Permeability:	-4.882
Pgp-inhibitor:	0.006	Pgp-substrate:	0.803
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):	0.003
20% Bioavailability (F20%):	0.009	30% Bioavailability (F30%):	0.279
50% Bioavailability (F50%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	50.539%	Volume Distribution (VD):	-0.38
Fu:	48.886% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.007
OATP1B3 inhibitor:	0.192	BCRP inhibitor:	0.0
BSEP inhibitor:	0.928

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.017	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.985 ? 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):

0.259

Half-life (T1/2):

1.701

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.2
Human Hepatotoxicity (H-HT):	0.599	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.768	Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.38	Skin Sensitization:	0.993
Carcinogencity:	0.807	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.614	Ototoxicity:	0.886
Hematotoxicity:	0.254	Drug-induced Nephrotoxicity:	0.887
Genotoxicity:	0.931	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.044	Hek293 Cytotoxicity:	0.304
BCF:	0.552 ? 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:	3.396 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.658 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.882 ? 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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14242	Maytenus laevis	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
Activity	6

Activity Type	# Activity
Cell line	6

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
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	110.1	pg/ml	PMID[17070063]
NPT927	Cell line	PBMC	Homo sapiens	Activity	=	136.1	pg/ml	PMID[17070063]
NPT927	Cell line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[20337486]

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 NPC473506 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	21494
0.1-0.2	27158
0.2-0.3	1090
0.3-0.4	58
0.4-0.5	35
0.5-0.6	16
0.6-0.7	6
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
0.6604	Remote Similarity	NPC475644
0.6449	Remote Similarity	NPC30456
0.6449	Remote Similarity	NPC488904
0.6168	Remote Similarity	NPC475303
0.6154	Remote Similarity	NPC475498
0.6055	Remote Similarity	NPC476110
0.5963	Remote Similarity	NPC87152
0.5963	Remote Similarity	NPC475600
0.5963	Remote Similarity	NPC475631
0.5909	Remote Similarity	NPC471190
0.5909	Remote Similarity	NPC475596
0.566	Remote Similarity	NPC76565
0.566	Remote Similarity	NPC601313
0.547	Remote Similarity	NPC327769
0.5398	Remote Similarity	NPC470486
0.5398	Remote Similarity	NPC471977
0.5285	Remote Similarity	NPC483854
0.5242	Remote Similarity	NPC482915
0.5221	Remote Similarity	NPC326930
0.5175	Remote Similarity	NPC475301
0.5091	Remote Similarity	NPC475137
0.5042	Remote Similarity	NPC477787

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4078
0.1-0.2	5024
0.2-0.3	48
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