NPASS Compound

Natural Product: NPC184747

Natural Product ID	NPC184747
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BLOHSDHMGDNCOV-UDJQVXKASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509571
PubChem CID	11600035
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 95 99 0 0 0 0 0 0 0 0999 V2000 10.1443 -2.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6443 -2.6836 0.0000 C 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 5.6443 -2.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8943 -3.9826 0.0000 O 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 3.3943 -1.3846 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 2.6443 -0.0855 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 5.2029 0.3656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5226 -0.6801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3520 1.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7615 0.8168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9106 1.7810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6501 3.2582 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 6.0915 2.8070 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 -0.4884 -2.4203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1096 -3.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6000 -3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4923 -2.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7432 -1.9324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0856 -2.6018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8120 -4.0766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3364 -1.7740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9423 -4.6353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0338 -6.1325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7829 -6.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3761 -6.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4676 -8.2991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8099 -8.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0608 -8.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9694 -6.6435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6270 -5.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7393 -3.2481 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 8.6443 -1.1836 0.0000 C 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 -4.1836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3271 -1.1948 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6443 -4.1836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1443 -4.1836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1443 -1.1836 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 4.0986 -0.0602 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1116 -0.3972 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2001 -0.6177 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3201 1.2679 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7992 4.2224 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9801 5.2484 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6820 3.3201 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4557 2.6480 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3038 1.7266 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 -2.3673 -0.8986 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 -1.7534 -1.6144 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2011 -5.2932 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2954 -4.3212 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1738 -5.4041 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5248 -3.8483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4771 -0.7999 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4423 -2.7874 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3623 -0.6333 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2167 -9.1269 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9014 -10.4657 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4032 -8.8101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2203 -5.8157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1760 -4.5435 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9902 -4.0760 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -1.9973 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0701 -4.5906 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3083 4.4783 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 4.1972 2.3599 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6443 0.3164 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1331 -1.0007 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1889 -0.8206 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 2 0 4 6 1 0 6 7 1 0 8 7 1 1 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 9 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 23 24 1 0 24 25 1 0 24 26 1 0 22 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 29 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 27 44 1 0 21 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 2 49 1 0 30 8 1 0 43 38 1 0 22 8 1 0 18 13 1 0 24 20 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 0 3 54 1 0 3 55 1 0 7 56 1 0 7 57 1 0 9 58 1 1 14 59 1 0 15 60 1 0 16 61 1 0 17 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 20 66 1 1 21 67 1 6 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 6 28 75 1 0 28 76 1 0 29 77 1 6 30 78 1 6 34 79 1 0 34 80 1 0 34 81 1 0 39 82 1 0 40 83 1 0 41 84 1 0 42 85 1 0 43 86 1 0 44 87 1 0 44 88 1 0 44 89 1 0 48 90 1 0 48 91 1 0 48 92 1 0 49 93 1 0 49 94 1 0 49 95 1 0 M END

Standard InCHIKey	BLOHSDHMGDNCOV-UDJQVXKASA-N
Standard InCHI	InChI=1S/C38H46O11/c1-22(2)18-31(41)44-21-37-30(48-35(43)27-16-12-9-13-17-27)20-28-32(45-24(4)39)38(37,49-36(28,6)7)23(3)19-29(33(37)46-25(5)40)47-34(42)26-14-10-8-11-15-26/h8-17,22-23,28-30,32-33H,18-21H2,1-7H3/t23-,28-,29+,30+,32-,33+,37-,38-/m1/s1
SMILES	CC(CC(=O)OC[C@@]12[C@@H](OC(=O)c3ccccc3)C[C@@H]3[C@H]([C@]2(OC3(C)C)[C@@H](C[C@@H]([C@@H]1OC(=O)C)OC(=O)c1ccccc1)C)OC(=O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	678.3	Volume:	690.713 ? Van der Waals volume.
Dense:	0.982	LogP:	4.315 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.727 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.6 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	31.0
TPSA:	140.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.233	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.894	Fsp³:	0.553
MCE-18:	166.169 ? 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:	0.916	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.173 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.185	Promiscuous compounds:	0.121

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002	MDCK Permeability:	-4.672
Pgp-inhibitor:	0.878	Pgp-substrate:	0.123
PAMPA:	0.224 ? 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%):	0.004	30% Bioavailability (F30%):	0.048
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815	MRP1:	1.0
Plasma Protein Binding (PPB):	93.787%	Volume Distribution (VD):	-0.3
Fu:	6.025% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.002
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

3.813

Half-life (T1/2):

0.699

ADMET: Toxicity

hERG Blockers:	0.111	hERG Blockers (10um):	0.64
Human Hepatotoxicity (H-HT):	0.137	Drug-induced Liver Injury (DILI):	0.913
AMES Toxicity:	0.346	Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.384	Skin Sensitization:	0.991
Carcinogencity:	0.517	Eye Corrosion:	0.0
Eye Irritation:	0.07	Respiratory Toxicity:	0.049
Drug-induced Neurotoxicity:	0.548	Ototoxicity:	0.371
Hematotoxicity:	0.038	Drug-induced Nephrotoxicity:	0.814
Genotoxicity:	0.37	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.3	Hek293 Cytotoxicity:	0.151
BCF:	0.934 ? 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:	4.103 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.806 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.468 ? 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]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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
IC50	2

Activity Type	# Activity
Cell line	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
NPT168	Cell line	P388	Mus musculus	IC50	=	51.0	nM	PMID[9784175]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	82.0	nM	PubChem BioAssay data set

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 NPC184747 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	15441
0.1-0.2	32347
0.2-0.3	1530
0.3-0.4	393
0.4-0.5	78
0.5-0.6	39
0.6-0.7	18
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8906	High Similarity	NPC4341
0.8333	Intermediate Similarity	NPC479047
0.8333	Intermediate Similarity	NPC191082
0.8333	Intermediate Similarity	NPC291638
0.8209	Intermediate Similarity	NPC139067
0.7714	Intermediate Similarity	NPC479044
0.7681	Intermediate Similarity	NPC67777
0.7681	Intermediate Similarity	NPC43241
0.7183	Intermediate Similarity	NPC177340
0.7059	Intermediate Similarity	NPC473081
0.6962	Remote Similarity	NPC75600
0.6962	Remote Similarity	NPC483884
0.6667	Remote Similarity	NPC17877
0.6571	Remote Similarity	NPC195647
0.6571	Remote Similarity	NPC270498
0.6364	Remote Similarity	NPC70716
0.6316	Remote Similarity	NPC41481
0.6282	Remote Similarity	NPC473613
0.6267	Remote Similarity	NPC137718
0.6216	Remote Similarity	NPC51314
0.6154	Remote Similarity	NPC97667
0.6133	Remote Similarity	NPC48017
0.6133	Remote Similarity	NPC147880
0.6111	Remote Similarity	NPC200592
0.6111	Remote Similarity	NPC610542
0.6076	Remote Similarity	NPC473085
0.6053	Remote Similarity	NPC27377
0.6026	Remote Similarity	NPC479043
0.5974	Remote Similarity	NPC471100
0.5974	Remote Similarity	NPC605884
0.5949	Remote Similarity	NPC95265
0.5897	Remote Similarity	NPC472574
0.5875	Remote Similarity	NPC473112
0.5844	Remote Similarity	NPC148062
0.5802	Remote Similarity	NPC479042
0.5789	Remote Similarity	NPC473060
0.5714	Remote Similarity	NPC246480
0.5679	Remote Similarity	NPC607428
0.5641	Remote Similarity	NPC147217
0.557	Remote Similarity	NPC254558
0.557	Remote Similarity	NPC171207
0.557	Remote Similarity	NPC471107
0.5541	Remote Similarity	NPC474608
0.5432	Remote Similarity	NPC266265
0.5385	Remote Similarity	NPC483902
0.5385	Remote Similarity	NPC472577
0.5375	Remote Similarity	NPC473673
0.5333	Remote Similarity	NPC176413
0.5333	Remote Similarity	NPC483885
0.5316	Remote Similarity	NPC483883
0.5316	Remote Similarity	NPC90257
0.5316	Remote Similarity	NPC483845
0.5316	Remote Similarity	NPC151585
0.5316	Remote Similarity	NPC69357
0.5309	Remote Similarity	NPC92293
0.5294	Remote Similarity	NPC88593
0.5287	Remote Similarity	NPC610134
0.5233	Remote Similarity	NPC479040
0.5181	Remote Similarity	NPC96903
0.5165	Remote Similarity	NPC294512
0.5165	Remote Similarity	NPC479045
0.5132	Remote Similarity	NPC283375
0.5132	Remote Similarity	NPC183122
0.5122	Remote Similarity	NPC483844
0.5116	Remote Similarity	NPC14499
0.5059	Remote Similarity	NPC483849
0.5057	Remote Similarity	NPC473109

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC184747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3370
0.1-0.2	5619
0.2-0.3	161
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