NPASS Compound

Natural Product: NPC139067

Natural Product ID	NPC139067
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Fokienagarofuran A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504778
PubChem CID	11571180
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 2D 93 98 0 0 0 0 0 0 0 0999 V2000 -1.5305 -1.3311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4980 -2.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1000 -3.7949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5903 -3.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4827 -2.7591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 -1.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3943 -1.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8943 -1.3846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6443 -2.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2309 -4.1255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1443 -2.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8943 -3.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3943 -3.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1443 -2.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3943 -1.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8943 -1.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 -0.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 0.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3442 2.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 1.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0788 2.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8068 3.2659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1935 3.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 0.8787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5329 2.3559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4009 3.3401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6820 3.3201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0915 2.8070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2406 3.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9801 5.2484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5706 5.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4215 4.7973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5151 -3.8472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9737 -3.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0252 -2.4275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0061 -4.5853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1642 -5.4030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1966 -6.4911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6552 -6.1411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7705 -7.9293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3119 -8.2794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1142 -9.7176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9182 -10.8057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3768 -10.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8029 -9.0175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6879 -0.3769 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6186 -2.3635 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7245 -0.0660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7489 -3.2470 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3586 -4.1449 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1914 -5.2921 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9327 -4.6342 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9472 -2.4347 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0986 -0.0602 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3943 -2.8846 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3082 -5.3634 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1443 -5.2817 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6443 -2.6836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1443 -0.0855 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1443 -0.0855 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0626 -0.5738 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2841 2.5838 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1378 2.0524 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6805 2.6860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6004 -0.7041 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0159 0.4364 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8615 2.0548 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5503 -0.9066 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6560 3.6844 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8384 2.0865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0040 2.8749 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0323 4.7182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1898 4.5893 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4371 2.6359 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3520 1.3298 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6501 3.2582 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1292 6.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3101 7.2387 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0119 5.3103 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8982 -5.7912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0943 -3.5529 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9180 -5.6178 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7205 -7.1912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5728 -10.0676 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4921 -12.2439 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4092 -11.5438 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2615 -8.6674 0.0000 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 1 0 5 6 1 0 6 7 1 1 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 6 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 22 23 1 0 23 24 1 0 23 25 1 0 20 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 17 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 5 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 4 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 21 2 1 0 38 33 1 0 51 46 1 0 21 6 1 0 16 11 1 0 23 19 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 6 3 56 1 0 3 57 1 0 4 58 1 6 5 59 1 6 7 60 1 0 7 61 1 0 12 62 1 0 13 63 1 0 14 64 1 0 15 65 1 0 16 66 1 0 17 67 1 1 18 68 1 0 18 69 1 0 19 70 1 1 20 71 1 6 24 72 1 0 24 73 1 0 24 74 1 0 25 75 1 0 25 76 1 0 25 77 1 0 29 78 1 0 29 79 1 0 29 80 1 0 34 81 1 0 35 82 1 0 36 83 1 0 37 84 1 0 38 85 1 0 42 86 1 0 42 87 1 0 42 88 1 0 47 89 1 0 48 90 1 0 49 91 1 0 50 92 1 0 51 93 1 0 M END

Standard InCHIKey	NDGTVMJNLFEYMW-NPIRVHPYSA-N
Standard InCHI	InChI=1S/C40H42O11/c1-24-21-31(49-36(44)28-17-11-7-12-18-28)34(48-26(3)42)39(23-46-35(43)27-15-9-6-10-16-27)32(50-37(45)29-19-13-8-14-20-29)22-30-33(47-25(2)41)40(24,39)51-38(30,4)5/h6-20,24,30-34H,21-23H2,1-5H3/t24-,30-,31+,32+,33-,34+,39-,40-/m1/s1
SMILES	C[C@@H]1C[C@@H]([C@@H]([C@@]2(COC(=O)c3ccccc3)[C@H](C[C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	698.27	Volume:	708.839 ? Van der Waals volume.
Dense:	0.985	LogP:	4.286 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.847 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.6 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	37.0
TPSA:	140.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.199	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.791	Fsp³:	0.425
MCE-18:	179.825 ? 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:	0.926	Fluc inhibitor:	0.162 ? 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:	0.416 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.231	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.192	MDCK Permeability:	-4.721
Pgp-inhibitor:	1.0	Pgp-substrate:	0.085
PAMPA:	0.037 ? 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%):	0.005	30% Bioavailability (F30%):	0.175
50% Bioavailability (F50%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.639	MRP1:	1.0
Plasma Protein Binding (PPB):	96.811%	Volume Distribution (VD):	-0.39
Fu:	2.799% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.947	BCRP inhibitor:	0.038
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.551
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.567
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.615
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.182	CYP3A4-substrate:	0.989
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):

2.096

Half-life (T1/2):

1.06

ADMET: Toxicity

hERG Blockers:	0.168	hERG Blockers (10um):	0.809
Human Hepatotoxicity (H-HT):	0.039	Drug-induced Liver Injury (DILI):	0.93
AMES Toxicity:	0.16	Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.453	Skin Sensitization:	0.989
Carcinogencity:	0.542	Eye Corrosion:	0.0
Eye Irritation:	0.084	Respiratory Toxicity:	0.034
Drug-induced Neurotoxicity:	0.683	Ototoxicity:	0.218
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.53
Genotoxicity:	0.16	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.31	Hek293 Cytotoxicity:	0.372
BCF:	0.911 ? 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:	4.439 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.726 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.612 ? 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
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[18471021]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[18471021]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	Stems	n.a.	n.a.	PMID[19534471]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22421	Microtropis japonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22423	Microtropis fokienensis	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
MIC	1
IC50	2

Activity Type	# Activity
Cell line	2
Organism	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
NPT168	Cell line	P388	Mus musculus	IC50	=	32.0	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	54.0	nM	PubChem BioAssay data set
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	85900.0	nM	DOI[10.6019/CHEMBL1201861]

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 NPC139067 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	15949
0.1-0.2	31888
0.2-0.3	1416
0.3-0.4	441
0.4-0.5	86
0.5-0.6	37
0.6-0.7	23
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9344	High Similarity	NPC67777
0.9344	High Similarity	NPC43241
0.8871	High Similarity	NPC4341
0.873	High Similarity	NPC177340
0.8281	Intermediate Similarity	NPC479047
0.8281	Intermediate Similarity	NPC191082
0.8281	Intermediate Similarity	NPC291638
0.8209	Intermediate Similarity	NPC184747
0.7778	Intermediate Similarity	NPC473081
0.7647	Intermediate Similarity	NPC479044
0.7463	Intermediate Similarity	NPC48017
0.7231	Intermediate Similarity	NPC195647
0.7231	Intermediate Similarity	NPC270498
0.6957	Remote Similarity	NPC246480
0.6883	Remote Similarity	NPC75600
0.6883	Remote Similarity	NPC483884
0.6857	Remote Similarity	NPC147217
0.6716	Remote Similarity	NPC200592
0.6716	Remote Similarity	NPC610542
0.6622	Remote Similarity	NPC473613
0.6575	Remote Similarity	NPC266265
0.6571	Remote Similarity	NPC17877
0.6486	Remote Similarity	NPC70716
0.6438	Remote Similarity	NPC472574
0.64	Remote Similarity	NPC473085
0.6267	Remote Similarity	NPC97667
0.6216	Remote Similarity	NPC41481
0.6216	Remote Similarity	NPC92293
0.6184	Remote Similarity	NPC473112
0.6164	Remote Similarity	NPC27377
0.6164	Remote Similarity	NPC137718
0.6111	Remote Similarity	NPC51314
0.6087	Remote Similarity	NPC474608
0.6081	Remote Similarity	NPC473673
0.6053	Remote Similarity	NPC95265
0.6027	Remote Similarity	NPC147880
0.5974	Remote Similarity	NPC607428
0.5921	Remote Similarity	NPC479043
0.5897	Remote Similarity	NPC479042
0.5867	Remote Similarity	NPC471100
0.5867	Remote Similarity	NPC605884
0.575	Remote Similarity	NPC88593
0.5733	Remote Similarity	NPC148062
0.5676	Remote Similarity	NPC473060
0.5658	Remote Similarity	NPC171207
0.5634	Remote Similarity	NPC283375
0.5634	Remote Similarity	NPC183122
0.56	Remote Similarity	NPC483883
0.56	Remote Similarity	NPC151585
0.5556	Remote Similarity	NPC14499
0.5479	Remote Similarity	NPC481047
0.5479	Remote Similarity	NPC481045
0.5455	Remote Similarity	NPC254558
0.5455	Remote Similarity	NPC471107
0.5402	Remote Similarity	NPC176413
0.5402	Remote Similarity	NPC483885
0.5263	Remote Similarity	NPC483902
0.5263	Remote Similarity	NPC472577
0.525	Remote Similarity	NPC96903
0.5227	Remote Similarity	NPC294512
0.5227	Remote Similarity	NPC479045
0.5195	Remote Similarity	NPC90257
0.5195	Remote Similarity	NPC483845
0.5195	Remote Similarity	NPC69357
0.5176	Remote Similarity	NPC610134
0.5128	Remote Similarity	NPC158663
0.5119	Remote Similarity	NPC479040
0.5065	Remote Similarity	NPC70973
0.5065	Remote Similarity	NPC163087
0.5065	Remote Similarity	NPC473111
0.5062	Remote Similarity	NPC210591
0.506	Remote Similarity	NPC483887
0.506	Remote Similarity	NPC158020

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC139067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3454
0.1-0.2	5528
0.2-0.3	167
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