NPASS Compound

Natural Product: NPC482259

Natural Product ID	NPC482259
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YTSGCMXOTIDJHF-DWGHEVHASA-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]

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 97100 0 0 0 0 0 0 0 0999 V2000 2.2719 -3.5211 -2.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8408 -3.4255 -0.6641 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4082 -3.1358 -0.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4181 -2.5973 -1.3627 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8438 -2.3415 -1.1084 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4660 -3.7539 -0.9773 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 -1.7836 -2.3597 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2246 -1.6368 0.1214 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9138 -0.2072 0.3041 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5242 0.2770 0.1659 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4235 -0.1516 1.2160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 -0.7072 2.3134 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8890 0.1325 1.1288 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5437 -0.2643 -0.1096 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5881 0.6989 -0.6584 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0696 -0.2020 -1.8361 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2732 0.3725 -2.4983 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4521 -1.4251 -1.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4334 -1.4671 0.1058 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7801 -2.7596 0.2344 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0876 -3.3835 1.2848 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1624 -1.1385 1.2765 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6608 0.7714 0.2340 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3011 1.9295 0.6277 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9058 3.0198 0.1599 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4198 1.8591 1.5763 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9934 1.5472 1.3439 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5422 2.0870 2.4730 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9793 1.3319 3.3720 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6440 3.5510 2.6836 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 1.7412 0.2617 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2838 2.5573 -0.7994 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1112 1.9847 -1.8417 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3815 4.0250 -0.7088 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0239 4.7860 -1.7962 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1131 6.1631 -1.7201 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5555 6.7742 -0.5682 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9166 6.0147 0.5286 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8231 4.6436 0.4397 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7296 0.4805 -0.7261 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7435 1.3274 -0.3663 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9919 1.5295 0.8349 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5460 2.0042 -1.3972 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6531 -1.7534 0.2718 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2665 -2.4494 1.2842 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4785 -3.0117 2.1207 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7056 -2.5666 1.4347 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2051 -3.2938 2.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5938 -3.4135 2.6455 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4652 -2.8161 1.7612 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9396 -2.1117 0.7398 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5910 -1.9829 0.5703 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4081 -2.5872 -2.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1550 -4.1682 -2.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4560 -4.1316 -2.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8740 -4.5636 -0.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 -3.4037 0.5287 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0051 -2.3400 -2.3243 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2172 -4.2113 -0.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5524 -3.5880 -1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1442 -4.3693 -1.8587 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4894 -1.3653 -2.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6155 -2.6057 -3.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8881 -1.0078 -2.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8411 -2.2210 0.9901 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3455 0.1491 1.2425 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1674 0.1180 -0.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0433 -0.8689 2.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6545 -1.0482 3.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3671 -0.3430 2.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8640 -0.4209 -0.9814 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2017 1.6319 -1.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2314 -0.3862 -2.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2551 1.4693 -2.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1866 -0.0004 -1.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3156 -0.0512 -3.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5466 -2.3422 -1.5894 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4922 -1.1998 -0.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7051 -1.9456 1.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4639 2.8440 2.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3392 1.0509 2.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4031 1.7506 1.0711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0955 4.1359 1.9369 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3016 3.8361 3.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7107 3.8956 2.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3261 4.2722 -2.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1743 6.7403 -2.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6358 7.8629 -0.4814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2708 6.4985 1.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1104 4.0379 1.3131 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0517 1.9181 -2.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5925 1.6322 -1.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5290 3.1034 -1.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5702 -3.7854 3.2151 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0042 -3.9793 3.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5510 -2.9089 1.8819 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1943 -1.4128 -0.2570 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 1 0 5 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 19 22 1 1 15 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 13 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 10 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 9 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 8 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 20 2 1 0 39 34 1 0 52 47 1 0 19 14 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 1 3 57 1 0 4 58 1 0 6 59 1 0 6 60 1 0 6 61 1 0 7 62 1 0 7 63 1 0 7 64 1 0 8 65 1 1 9 66 1 1 10 67 1 6 12 68 1 0 12 69 1 0 13 70 1 1 14 71 1 6 15 72 1 6 16 73 1 6 17 74 1 0 17 75 1 0 17 76 1 0 18 77 1 0 18 78 1 0 22 79 1 0 26 80 1 0 26 81 1 0 26 82 1 0 30 83 1 0 30 84 1 0 30 85 1 0 35 86 1 0 36 87 1 0 37 88 1 0 38 89 1 0 39 90 1 0 43 91 1 0 43 92 1 0 43 93 1 0 48 94 1 0 49 95 1 0 50 96 1 0 52 97 1 0 M END

Standard InCHIKey	YTSGCMXOTIDJHF-DWGHEVHASA-N
Standard InCHI	InChI=1S/C39H45NO12/c1-21-16-17-38(7,8)35(52-37(46)28-15-12-18-40-20-28)33(50-26(6)43)32(51-36(45)27-13-10-9-11-14-27)23(3)31(49-25(5)42)29-30(48-24(4)41)22(2)19-39(29,47)34(21)44/h9-18,20-22,29-33,35,47H,3,19H2,1-2,4-8H3/b17-16+/t21-,22+,29-,30+,31+,32+,33-,35-,39-/m1/s1
SMILES	C[C@@H]1/C=C/C(C)(C)[C@@H]([C@@H]([C@H](C(=C)[C@@H]([C@H]2[C@H]([C@@H](C)C[C@@]2(C1=O)O)OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1cccnc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	719.29	Volume:	728.443 ? Van der Waals volume.
Dense:	0.987	LogP:	2.867 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.019 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.964 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	35.0
TPSA:	181.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.242	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.664	Fsp³:	0.462
MCE-18:	118.509 ? 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:	0.64	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.204 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.034	Promiscuous compounds:	0.088

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.379	MDCK Permeability:	-4.91
Pgp-inhibitor:	1.0	Pgp-substrate:	0.004
PAMPA:	0.354 ? 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%):	0.968	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	95.588%	Volume Distribution (VD):	-0.045
Fu:	4.466% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.963	BCRP inhibitor:	0.003
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.985
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.02
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

3.763

Half-life (T1/2):

0.959

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.097
Human Hepatotoxicity (H-HT):	0.164	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.199	Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.163	Skin Sensitization:	0.987
Carcinogencity:	0.392	Eye Corrosion:	0.0
Eye Irritation:	0.036	Respiratory Toxicity:	0.02
Drug-induced Neurotoxicity:	0.356	Ototoxicity:	0.28
Hematotoxicity:	0.12	Drug-induced Nephrotoxicity:	0.868
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.127
A549 Cytotoxicity:	0.335	Hek293 Cytotoxicity:	0.382
BCF:	0.738 ? 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:	3.497 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.161 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.751 ? 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
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27447736]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32233482]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	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
IC50	1

Activity Type	# Activity
Cell line	1

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
NPT25056	Cell line	BMDM	n.a.	IC50	>	10000.0	nM	PMID[32233482]

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 NPC482259 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	10220
0.1-0.2	36870
0.2-0.3	2215
0.3-0.4	422
0.4-0.5	92
0.5-0.6	27
0.6-0.7	5
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
0.7975	Intermediate Similarity	NPC482266
0.7701	Intermediate Similarity	NPC482264
0.7386	Intermediate Similarity	NPC482258
0.7143	Intermediate Similarity	NPC482260
0.7093	Intermediate Similarity	NPC482201
0.6596	Remote Similarity	NPC482261
0.6484	Remote Similarity	NPC482433
0.6222	Remote Similarity	NPC482263
0.6082	Remote Similarity	NPC482262
0.6	Remote Similarity	NPC482316
0.5909	Remote Similarity	NPC473497
0.5889	Remote Similarity	NPC265459
0.5889	Remote Similarity	NPC482265
0.5714	Remote Similarity	NPC482249
0.5684	Remote Similarity	NPC482202
0.5667	Remote Similarity	NPC228674
0.5625	Remote Similarity	NPC482155
0.5591	Remote Similarity	NPC482267
0.5567	Remote Similarity	NPC482204
0.5566	Remote Similarity	NPC605558
0.5556	Remote Similarity	NPC482313
0.5543	Remote Similarity	NPC482247
0.5543	Remote Similarity	NPC482304
0.5464	Remote Similarity	NPC482250
0.54	Remote Similarity	NPC187494
0.5385	Remote Similarity	NPC233727
0.5376	Remote Similarity	NPC290833
0.5354	Remote Similarity	NPC482154
0.5213	Remote Similarity	NPC475262
0.5158	Remote Similarity	NPC482248
0.5158	Remote Similarity	NPC285221
0.5158	Remote Similarity	NPC482251
0.5104	Remote Similarity	NPC482268
0.5104	Remote Similarity	NPC475660
0.5053	Remote Similarity	NPC482309
0.5052	Remote Similarity	NPC482255
0.5051	Remote Similarity	NPC317191

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482259 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2844
0.1-0.2	6166
0.2-0.3	137
0.3-0.4	3
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