NPASS Compound

Natural Product: NPC260786

Natural Product ID	NPC260786
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QOSLYAARSBMQOF-NBJLYKDOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL520853
PubChem CID	198036
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 72 75 0 0 0 0 0 0 0 0999 V2000 7.8679 -1.1862 0.8219 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5516 -1.3963 0.1300 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4317 -0.6186 0.7994 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8378 0.8521 0.7222 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1671 -0.7675 0.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1774 -1.4727 -1.0004 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0051 -0.1668 0.4279 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7748 -0.3065 -0.3058 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2437 -1.6804 -0.4622 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1053 -1.9423 0.0717 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0395 -2.9845 1.1996 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8747 -0.7338 0.5868 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6528 0.3846 -0.3330 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3576 1.6358 -0.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4901 1.9690 0.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2624 0.9962 1.3070 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3494 -0.2598 0.4755 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2408 -1.1749 0.8931 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7052 -2.4678 0.4141 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0311 -2.4498 0.3671 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9642 -3.5486 -0.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5138 -1.1253 0.8015 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6101 -0.8075 1.3098 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2332 0.0540 -0.8503 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8432 3.3930 0.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0042 3.8270 -0.0755 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3013 3.8031 0.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6780 3.2682 1.2999 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3948 4.3913 -0.6053 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 0.7811 -0.1856 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6664 0.6948 -1.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9910 0.3786 -2.7152 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7097 1.7915 -1.5393 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2090 -0.3946 1.7944 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7878 -0.4188 1.6261 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6701 -0.8965 0.0952 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2192 -2.1225 1.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2864 -2.4825 0.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6640 -1.1117 -0.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3492 -0.8777 1.8554 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4187 1.0076 -0.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3454 1.1905 1.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9051 1.4608 0.6149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9668 -2.4005 0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3551 -1.9593 -1.5539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7217 -2.3340 -0.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0095 -4.0037 0.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9606 -2.7904 1.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7859 -2.8107 1.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8042 0.0254 -1.3779 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9243 2.4810 -0.6949 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2620 1.2592 1.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7136 0.7695 2.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3581 -1.2353 2.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1926 -3.3742 0.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8623 -3.4690 0.5757 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4568 -4.5305 0.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2777 -3.4571 -1.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9846 -0.3583 -1.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7025 3.7891 1.5224 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0068 3.9580 -0.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0668 4.9495 0.0791 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9759 3.6284 -1.1287 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9429 5.1290 -1.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0541 1.5852 0.5618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7516 0.5152 -3.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2493 1.2087 -2.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5131 -0.5943 -2.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6675 1.4354 -1.9226 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8712 2.3107 -0.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2921 2.5565 -2.2302 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6995 -0.7689 2.5742 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 3 5 1 0 5 6 2 0 5 7 1 0 8 7 1 1 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 2 0 17 24 1 6 15 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 13 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 12 34 1 1 30 8 1 0 31 8 1 0 18 12 1 0 22 17 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 2 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 4 43 1 0 9 44 1 0 9 45 1 0 10 46 1 6 11 47 1 0 11 48 1 0 11 49 1 0 13 50 1 6 14 51 1 0 16 52 1 0 16 53 1 0 18 54 1 1 19 55 1 0 21 56 1 0 21 57 1 0 21 58 1 0 24 59 1 0 25 60 1 0 25 61 1 0 29 62 1 0 29 63 1 0 29 64 1 0 30 65 1 1 32 66 1 0 32 67 1 0 32 68 1 0 33 69 1 0 33 70 1 0 33 71 1 0 34 72 1 0 M END

Standard InCHIKey	QOSLYAARSBMQOF-NBJLYKDOSA-N
Standard InCHI	InChI=1S/C27H38O7/c1-8-14(2)23(30)34-26-11-16(4)27(32)19(21(26)24(26,6)7)10-18(13-33-17(5)28)12-25(31)20(27)9-15(3)22(25)29/h9-10,14,16,19-21,31-32H,8,11-13H2,1-7H3/t14?,16-,19+,20-,21-,25-,26+,27-/m1/s1
SMILES	CCC(C)C(=O)O[C@@]12C[C@@H](C)[C@]3([C@@H](C=C(C[C@]4([C@H]3C=C(C)C4=O)O)COC(=O)C)[C@@H]1C2(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	474.26	Volume:	489.672 ? Van der Waals volume.
Dense:	0.969	LogP:	2.738 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.98 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.682 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	21.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.465	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.084	Fsp³:	0.741
MCE-18:	82.468 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.303	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.061 ? 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:	0.301	Promiscuous compounds:	0.287

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.945	MDCK Permeability:	-4.611
Pgp-inhibitor:	0.505	Pgp-substrate:	0.576
PAMPA:	0.81 ? 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):	0.051
20% Bioavailability (F20%):	0.853	30% Bioavailability (F30%):	0.966
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037	MRP1:	0.976
Plasma Protein Binding (PPB):	56.927%	Volume Distribution (VD):	-0.027
Fu:	48.404% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.006
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.029	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.18	CYP2C19-substrate:	0.022
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.657
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	0.09
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
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):

6.973

Half-life (T1/2):

0.803

ADMET: Toxicity

hERG Blockers:	0.104	hERG Blockers (10um):	0.318
Human Hepatotoxicity (H-HT):	0.505	Drug-induced Liver Injury (DILI):	0.351
AMES Toxicity:	0.449	Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.434	Skin Sensitization:	0.824
Carcinogencity:	0.68	Eye Corrosion:	0.019
Eye Irritation:	0.325	Respiratory Toxicity:	0.506
Drug-induced Neurotoxicity:	0.281	Ototoxicity:	0.399
Hematotoxicity:	0.715	Drug-induced Nephrotoxicity:	0.575
Genotoxicity:	0.489	RPMI-8226 Immunitoxicity:	0.103
A549 Cytotoxicity:	0.084	Hek293 Cytotoxicity:	0.178
BCF:	0.795 ? 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:	3.588 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.515 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.914 ? 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
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11281	Euphorbia fortissima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18714.1	Rauvolfia verticillata var. hainanensis	Varieties	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18714.1	Rauvolfia verticillata var. hainanensis	Varieties	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11281	Euphorbia fortissima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18714.1	Rauvolfia verticillata var. hainanensis	Varieties	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11281	Euphorbia fortissima	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
Activity	2

Activity Type	# Activity
Organism	2

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.5	nmol	PMID[3236005]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.7	/nmol	PMID[3236005]

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 NPC260786 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	15920
0.1-0.2	32254
0.2-0.3	1559
0.3-0.4	51
0.4-0.5	30
0.5-0.6	19
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8983	High Similarity	NPC174471
0.8793	High Similarity	NPC96739
0.8095	Intermediate Similarity	NPC474871
0.7619	Intermediate Similarity	NPC475937
0.7463	Intermediate Similarity	NPC170212
0.7286	Intermediate Similarity	NPC474937
0.7206	Intermediate Similarity	NPC17138
0.7206	Intermediate Similarity	NPC101825
0.7206	Intermediate Similarity	NPC215643
0.7206	Intermediate Similarity	NPC265499
0.7101	Intermediate Similarity	NPC221511
0.6986	Remote Similarity	NPC602538
0.6944	Remote Similarity	NPC479000
0.6806	Remote Similarity	NPC151216
0.6806	Remote Similarity	NPC183540
0.6806	Remote Similarity	NPC89227
0.6769	Remote Similarity	NPC158523
0.6761	Remote Similarity	NPC475391
0.6719	Remote Similarity	NPC153036
0.6719	Remote Similarity	NPC91189
0.6447	Remote Similarity	NPC159692
0.6316	Remote Similarity	NPC222307
0.6301	Remote Similarity	NPC482317
0.6087	Remote Similarity	NPC71889
0.589	Remote Similarity	NPC482454
0.5833	Remote Similarity	NPC485736
0.5833	Remote Similarity	NPC277477
0.5833	Remote Similarity	NPC482397
0.5833	Remote Similarity	NPC479003
0.5833	Remote Similarity	NPC485735
0.5833	Remote Similarity	NPC485733
0.5833	Remote Similarity	NPC482396
0.5479	Remote Similarity	NPC478681
0.5455	Remote Similarity	NPC485731
0.5455	Remote Similarity	NPC485732
0.5333	Remote Similarity	NPC472758
0.5326	Remote Similarity	NPC102367
0.5326	Remote Similarity	NPC478683
0.5325	Remote Similarity	NPC474872
0.5269	Remote Similarity	NPC478682
0.5244	Remote Similarity	NPC153651
0.5063	Remote Similarity	NPC477091
0.506	Remote Similarity	NPC472760

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC260786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6479
0.1-0.2	2647
0.2-0.3	24
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