NPASS Compound

Natural Product: NPC66761

Natural Product ID	NPC66761
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZFYHVMQCJIKTLP-LLWUNBJKSA-N
IUPAC Name	n.a.
Synonyms	Celafolin C-1
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL511093
PubChem CID	44593422
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 73 76 0 0 0 0 0 0 0 0999 V2000 0.9479 -4.1026 -3.2107 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1950 -3.2814 -1.9917 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3056 -3.3622 -1.3628 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2774 -2.4090 -1.4754 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5144 -1.6123 -0.2946 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5885 -2.0448 0.6332 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8616 -1.5444 -0.0962 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9159 -2.3755 -0.0288 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6459 -3.1083 -0.8799 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2459 -2.9941 -2.0379 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8023 -3.9707 -0.5419 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8388 -0.1892 0.4326 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7714 0.6128 -0.3297 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4394 -0.1472 -0.6656 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6035 0.4685 -0.1196 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7029 0.8536 -0.8750 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6147 0.6418 -2.1342 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8883 1.4534 -0.3196 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9111 1.8440 -1.1577 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0538 2.4008 -0.5905 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1523 2.5538 0.7668 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1204 2.1581 1.5921 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0006 1.6128 1.0416 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3625 1.0092 -1.7052 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6029 1.8910 0.4001 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9030 2.6907 0.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1140 1.9659 0.7630 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1590 0.5058 0.4686 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0775 0.1675 -0.6867 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3389 2.7845 -0.1868 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2338 3.4255 0.6514 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2079 3.2123 1.9044 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2551 4.3807 0.1492 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3970 -0.2424 1.7803 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6221 -1.3692 1.9489 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6846 -0.9704 2.5417 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2557 -2.3336 2.9725 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7835 -4.7908 -3.3337 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9754 -3.4059 -4.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0490 -4.5588 -3.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5157 -1.8781 0.0243 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6137 -3.1420 0.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6584 -1.5247 -1.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7695 -3.5567 -0.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7616 -4.1426 0.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6922 -4.9579 -1.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6866 -0.1575 -1.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8909 1.7496 -2.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8857 2.7232 -1.2136 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0368 2.9867 1.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1821 2.2712 2.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1945 1.3063 1.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3786 0.1258 -2.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2481 1.6012 -1.6626 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5524 1.6667 -2.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3575 1.8058 1.4791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6940 3.5410 1.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9372 3.2278 -0.5845 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3605 2.2254 1.8381 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9873 2.4264 0.2052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6914 0.0677 1.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9023 -0.5488 -0.3956 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5698 -0.3298 -1.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6478 1.0712 -1.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5084 4.1103 -0.8884 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8367 5.4108 0.1251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1220 4.3669 0.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -1.4127 3.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7581 0.1373 2.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5719 -1.3137 1.9705 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7755 -3.1469 2.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4971 -2.7917 3.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9331 -1.7377 3.6312 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 7 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 13 24 1 6 13 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 25 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 12 34 1 1 34 35 1 0 35 36 1 0 35 37 1 0 14 5 1 0 23 18 1 0 35 6 1 0 28 12 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 1 6 42 1 1 7 43 1 6 11 44 1 0 11 45 1 0 11 46 1 0 14 47 1 6 19 48 1 0 20 49 1 0 21 50 1 0 22 51 1 0 23 52 1 0 24 53 1 0 24 54 1 0 24 55 1 0 25 56 1 1 26 57 1 0 26 58 1 0 27 59 1 0 27 60 1 0 28 61 1 1 29 62 1 0 29 63 1 0 29 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 36 68 1 0 36 69 1 0 36 70 1 0 37 71 1 0 37 72 1 0 37 73 1 0 M END

Standard InCHIKey	ZFYHVMQCJIKTLP-LLWUNBJKSA-N
Standard InCHI	InChI=1S/C28H36O9/c1-15-13-14-20(33-16(2)29)27(7)24(36-25(32)19-11-9-8-10-12-19)22(34-17(3)30)21-23(35-18(4)31)28(15,27)37-26(21,5)6/h8-12,15,20-24H,13-14H2,1-7H3/t15-,20+,21-,22-,23-,24+,27+,28-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@@H]2[C@@H](OC(=O)C)[C@]3([C@@]([C@H]1OC(=O)c1ccccc1)(C)[C@H](CC[C@H]3C)OC(=O)C)OC2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.24	Volume:	519.275 ? Van der Waals volume.
Dense:	0.994	LogP:	2.85 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.821 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.398 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	24.0
TPSA:	114.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.427	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.627	Fsp³:	0.643
MCE-18:	143.304 ? 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:	0.363	Fluc inhibitor:	0.021 ? 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:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.278	Promiscuous compounds:	0.082

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.019	MDCK Permeability:	-4.745
Pgp-inhibitor:	1.0	Pgp-substrate:	0.317
PAMPA:	0.167 ? 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):	0.002
20% Bioavailability (F20%):	0.719	30% Bioavailability (F30%):	0.976
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.999
Plasma Protein Binding (PPB):	69.088%	Volume Distribution (VD):	-0.419
Fu:	27.462% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.846	BCRP inhibitor:	0.064
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.442
CYP2C19-inhibitor:	0.019	CYP2C19-substrate:	0.038
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.273	CYP3A4-substrate:	0.013
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.983 ? 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):

6.086

Half-life (T1/2):

0.419

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.283
Human Hepatotoxicity (H-HT):	0.217	Drug-induced Liver Injury (DILI):	0.73
AMES Toxicity:	0.531	Rat Oral Acute Toxicity:	0.391
Maximum Recommended Daily Dose:	0.296	Skin Sensitization:	0.965
Carcinogencity:	0.673	Eye Corrosion:	0.047
Eye Irritation:	0.598	Respiratory Toxicity:	0.138
Drug-induced Neurotoxicity:	0.138	Ototoxicity:	0.249
Hematotoxicity:	0.121	Drug-induced Nephrotoxicity:	0.519
Genotoxicity:	0.731	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.068	Hek293 Cytotoxicity:	0.185
BCF:	0.664 ? 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:	3.582 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.22 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.72 ? 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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350085]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[8350085]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	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
Ratio IC50	5
IC50	5
Activity	8
Inhibition	4

Activity Type	# Activity
Cell line	5
Unchecked	4
Individual protein	9
Others	4

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	Ratio IC50	=	2.1	n.a.	PMID[33683135]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	23.0	n.a.	PMID[33683135]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	IC50	=	240.0	nM	PMID[33683135]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	IC50	=	34.0	nM	PMID[33683135]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	Open TG-GATES in vivo data: Hematology
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[17958396]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	6800.0	nM	PMID[26546220]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	2.4	%	PMID[33683135]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	3.2	%	PMID[33683135]
NPT2	Others	Unspecified	n.a.	Activity	=	15.3	%	PMID[17958396]
NPT2	Others	Unspecified	n.a.	Activity	=	52.8	%	PMID[15387665]
NPT2	Others	Unspecified	n.a.	Activity	=	90.6	%	PMID[8277313]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[8277313]

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 NPC66761 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	16291
0.1-0.2	31485
0.2-0.3	1563
0.3-0.4	353
0.4-0.5	74
0.5-0.6	57
0.6-0.7	18
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC483843
0.9286	High Similarity	NPC211137
0.9286	High Similarity	NPC476094
0.8621	High Similarity	NPC475429
0.7812	Intermediate Similarity	NPC473758
0.7778	Intermediate Similarity	NPC90257
0.7778	Intermediate Similarity	NPC69357
0.7536	Intermediate Similarity	NPC4421
0.7231	Intermediate Similarity	NPC483845
0.7164	Intermediate Similarity	NPC483844
0.7143	Intermediate Similarity	NPC481047
0.7143	Intermediate Similarity	NPC481045
0.7042	Intermediate Similarity	NPC212768
0.6857	Remote Similarity	NPC483848
0.6825	Remote Similarity	NPC474608
0.6667	Remote Similarity	NPC90614
0.6562	Remote Similarity	NPC283375
0.6528	Remote Similarity	NPC483849
0.6471	Remote Similarity	NPC163719
0.6471	Remote Similarity	NPC95810
0.6418	Remote Similarity	NPC483847
0.6418	Remote Similarity	NPC483862
0.6338	Remote Similarity	NPC609924
0.6308	Remote Similarity	NPC183122
0.6269	Remote Similarity	NPC118080
0.6234	Remote Similarity	NPC473115
0.6176	Remote Similarity	NPC470152
0.6087	Remote Similarity	NPC473060
0.6081	Remote Similarity	NPC481050
0.6	Remote Similarity	NPC483887
0.6	Remote Similarity	NPC158020
0.5942	Remote Similarity	NPC475759
0.5921	Remote Similarity	NPC603877
0.5867	Remote Similarity	NPC609221
0.5857	Remote Similarity	NPC483886
0.5775	Remote Similarity	NPC48017
0.5775	Remote Similarity	NPC246841
0.5775	Remote Similarity	NPC200471
0.5775	Remote Similarity	NPC472575
0.5714	Remote Similarity	NPC241951
0.5694	Remote Similarity	NPC147217
0.5694	Remote Similarity	NPC483842
0.5694	Remote Similarity	NPC137718
0.5694	Remote Similarity	NPC148062
0.5676	Remote Similarity	NPC479043
0.5672	Remote Similarity	NPC147561
0.5634	Remote Similarity	NPC17877
0.5634	Remote Similarity	NPC51314
0.56	Remote Similarity	NPC210591
0.557	Remote Similarity	NPC125106
0.557	Remote Similarity	NPC472573
0.5556	Remote Similarity	NPC246480
0.5556	Remote Similarity	NPC147880
0.5526	Remote Similarity	NPC475652
0.5513	Remote Similarity	NPC608007
0.5507	Remote Similarity	NPC473081
0.5507	Remote Similarity	NPC195647
0.55	Remote Similarity	NPC301368
0.55	Remote Similarity	NPC84815
0.5467	Remote Similarity	NPC57628
0.5467	Remote Similarity	NPC252314
0.5467	Remote Similarity	NPC481059
0.5417	Remote Similarity	NPC281717
0.5417	Remote Similarity	NPC163087
0.5417	Remote Similarity	NPC87448
0.5405	Remote Similarity	NPC473088
0.5385	Remote Similarity	NPC475039
0.5385	Remote Similarity	NPC476035
0.5333	Remote Similarity	NPC306146
0.5333	Remote Similarity	NPC483841
0.5301	Remote Similarity	NPC253738
0.5286	Remote Similarity	NPC200592
0.5286	Remote Similarity	NPC301556
0.5286	Remote Similarity	NPC100913
0.5286	Remote Similarity	NPC270498
0.5286	Remote Similarity	NPC610542
0.527	Remote Similarity	NPC483846
0.525	Remote Similarity	NPC479040
0.5244	Remote Similarity	NPC483864
0.519	Remote Similarity	NPC29704
0.519	Remote Similarity	NPC470157
0.5135	Remote Similarity	NPC483883
0.5135	Remote Similarity	NPC151585
0.5125	Remote Similarity	NPC475122
0.5067	Remote Similarity	NPC472572
0.5065	Remote Similarity	NPC472569
0.5065	Remote Similarity	NPC16912
0.5062	Remote Similarity	NPC488899

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4125
0.1-0.2	4840
0.2-0.3	185
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