NPASS Compound

Natural Product: NPC474608

Natural Product ID	NPC474608
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DDIPYHPAIWOAAM-BFHJBHDXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL476704
PubChem CID	44584510
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 67 70 0 0 0 0 0 0 0 0999 V2000 -3.6353 0.0567 1.0767 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1593 0.2327 1.2815 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9362 1.7455 1.4507 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4080 1.8672 1.5666 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0684 1.7660 0.1295 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4894 0.5860 -0.5968 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3574 1.0095 -1.7739 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6752 -0.1684 -1.1980 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3537 -1.5572 -1.6301 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5914 -2.3012 -0.7726 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8328 -1.3983 -0.6092 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2538 -0.3897 0.3134 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2158 -1.0258 1.0387 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1752 -2.3418 0.6850 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1812 -3.1309 1.4896 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1581 -2.9897 0.8145 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8891 -2.1638 -0.1564 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9732 -2.3979 -0.9906 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9425 -1.8927 -2.1410 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1469 -3.2017 -0.5975 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8160 -0.0863 -0.3744 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0013 0.5527 -0.7568 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9954 1.0648 -1.9084 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1667 0.6318 0.0969 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2912 1.2771 -0.3595 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4385 1.3735 0.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4123 0.8064 1.6950 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2905 0.1639 2.1477 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1510 0.0699 1.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4508 2.9435 -0.5058 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3738 3.9292 -0.9787 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 3.7654 -0.8355 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2237 5.1201 -1.6246 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0108 0.2853 0.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9821 -0.9277 1.4977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1356 0.8049 1.7659 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9738 -0.1562 2.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3154 2.2921 0.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3712 2.0780 2.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1971 2.8604 1.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0191 1.0509 2.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1518 1.8638 0.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1541 2.0828 -2.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4253 0.9559 -1.5777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0989 0.4449 -2.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9532 0.3857 -2.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0389 -1.5602 -2.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3197 -2.1231 -1.6825 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8345 -3.2640 -1.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0070 -1.0360 -1.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6793 -3.9135 0.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6285 -3.6382 2.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9591 -2.5242 1.9561 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4296 -3.4807 -0.1660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1224 -3.8623 1.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9649 -2.3499 1.1764 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0320 -2.7832 -1.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9929 -4.2233 -1.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3407 -3.1935 0.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3286 1.7284 -1.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3242 1.8694 0.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2748 0.8640 2.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3100 -0.2701 3.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3008 -0.4487 1.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2116 5.2957 -1.1508 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3900 4.9398 -2.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3736 6.0362 -1.4379 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 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 1 0 14 15 1 0 14 16 1 0 11 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 8 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 5 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 12 2 1 0 29 24 1 0 12 6 1 0 14 10 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 1 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 1 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 6 9 47 1 0 9 48 1 0 10 49 1 6 11 50 1 6 15 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 16 56 1 0 20 57 1 0 20 58 1 0 20 59 1 0 25 60 1 0 26 61 1 0 27 62 1 0 28 63 1 0 29 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 M END

Standard InCHIKey	DDIPYHPAIWOAAM-BFHJBHDXSA-N
Standard InCHI	InChI=1S/C26H34O7/c1-15-12-13-20(30-16(2)27)25(6)21(32-23(29)18-10-8-7-9-11-18)14-19-22(31-17(3)28)26(15,25)33-24(19,4)5/h7-11,15,19-22H,12-14H2,1-6H3/t15-,19-,20+,21+,22-,25+,26-/m1/s1
SMILES	C[C@@H]1CC[C@@H]([C@@]2(C)[C@H](C[C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.23	Volume:	469.739 ? Van der Waals volume.
Dense:	0.975	LogP:	3.232 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.115 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.49 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	23.0
TPSA:	88.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.496	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.474	Fsp³:	0.654
MCE-18:	135.349 ? 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:	0.273	Fluc inhibitor:	0.155 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.287	Promiscuous compounds:	0.157

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.949	MDCK Permeability:	-4.686
Pgp-inhibitor:	0.971	Pgp-substrate:	0.231
PAMPA:	0.299 ? 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%):	0.136	30% Bioavailability (F30%):	0.16
50% Bioavailability (F50%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.623	MRP1:	0.998
Plasma Protein Binding (PPB):	90.339%	Volume Distribution (VD):	-0.353
Fu:	9.025% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.916	BCRP inhibitor:	0.232
BSEP inhibitor:	0.926

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.398
CYP2C19-inhibitor:	0.086	CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.038	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.503 ? 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):

6.492

Half-life (T1/2):

0.419

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.382
Human Hepatotoxicity (H-HT):	0.273	Drug-induced Liver Injury (DILI):	0.878
AMES Toxicity:	0.636	Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.314	Skin Sensitization:	0.996
Carcinogencity:	0.825	Eye Corrosion:	0.04
Eye Irritation:	0.877	Respiratory Toxicity:	0.175
Drug-induced Neurotoxicity:	0.323	Ototoxicity:	0.167
Hematotoxicity:	0.111	Drug-induced Nephrotoxicity:	0.463
Genotoxicity:	0.895	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.26	Hek293 Cytotoxicity:	0.404
BCF:	0.686 ? 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:	3.65 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.179 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.706 ? 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
NPO40494	Maytenus bilocularis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27120798]
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]
NPO31542	Celastrus stephanotiifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	4
Ratio IC50	4
Activity	8
Inhibition	5

Activity Type	# Activity
Cell line	4
Unchecked	4
Individual protein	8
Others	4
Non-molecular	1

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	IC50	=	210.0	nM	PMID[33683135]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	52.2	n.a.	PMID[33683135]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	IC50	=	15.0	nM	PMID[33683135]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	2.4	n.a.	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[15043445]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	-1.1	%	PMID[33683135]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	0.7	%	PMID[33683135]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	>	30.0	%	PMID[27120798]
NPT2	Others	Unspecified	n.a.	Activity	=	26.2	%	PMID[17958396]
NPT2	Others	Unspecified	n.a.	Activity	=	47.9	%	PMID[15387665]
NPT2	Others	Unspecified	n.a.	Activity	=	92.1	%	PMID[8350094]
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 NPC474608 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	15372
0.1-0.2	32096
0.2-0.3	1882
0.3-0.4	339
0.4-0.5	93
0.5-0.6	43
0.6-0.7	20
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC283375
0.8571	High Similarity	NPC183122
0.7969	Intermediate Similarity	NPC210591
0.7742	Intermediate Similarity	NPC48017
0.7581	Intermediate Similarity	NPC17877
0.7581	Intermediate Similarity	NPC163087
0.7576	Intermediate Similarity	NPC475652
0.7353	Intermediate Similarity	NPC475039
0.7213	Intermediate Similarity	NPC473081
0.7213	Intermediate Similarity	NPC195647
0.7188	Intermediate Similarity	NPC246480
0.7101	Intermediate Similarity	NPC476035
0.6825	Remote Similarity	NPC211137
0.6825	Remote Similarity	NPC66761
0.6825	Remote Similarity	NPC483843
0.6667	Remote Similarity	NPC200592
0.6667	Remote Similarity	NPC270498
0.6667	Remote Similarity	NPC610542
0.6615	Remote Similarity	NPC311175
0.6615	Remote Similarity	NPC483847
0.6562	Remote Similarity	NPC475429
0.6562	Remote Similarity	NPC476094
0.6418	Remote Similarity	NPC483883
0.6418	Remote Similarity	NPC151585
0.6364	Remote Similarity	NPC475759
0.6364	Remote Similarity	NPC470152
0.6349	Remote Similarity	NPC147561
0.6154	Remote Similarity	NPC100913
0.6111	Remote Similarity	NPC473112
0.6087	Remote Similarity	NPC139067
0.6087	Remote Similarity	NPC43241
0.6	Remote Similarity	NPC473758
0.5942	Remote Similarity	NPC4341
0.5942	Remote Similarity	NPC479047
0.5942	Remote Similarity	NPC291638
0.5915	Remote Similarity	NPC472574
0.5915	Remote Similarity	NPC41481
0.589	Remote Similarity	NPC607428
0.5857	Remote Similarity	NPC27377
0.5775	Remote Similarity	NPC473673
0.5714	Remote Similarity	NPC90257
0.5714	Remote Similarity	NPC483845
0.5714	Remote Similarity	NPC69357
0.5694	Remote Similarity	NPC479044
0.5676	Remote Similarity	NPC473613
0.5676	Remote Similarity	NPC473085
0.5652	Remote Similarity	NPC1408
0.5634	Remote Similarity	NPC67777
0.5634	Remote Similarity	NPC483842
0.5634	Remote Similarity	NPC158663
0.5634	Remote Similarity	NPC177340
0.5625	Remote Similarity	NPC481065
0.5616	Remote Similarity	NPC266265
0.5556	Remote Similarity	NPC171207
0.5541	Remote Similarity	NPC184747
0.5493	Remote Similarity	NPC191082
0.5479	Remote Similarity	NPC306146
0.5479	Remote Similarity	NPC483841
0.5479	Remote Similarity	NPC92293
0.5479	Remote Similarity	NPC483844
0.5455	Remote Similarity	NPC88593
0.5455	Remote Similarity	NPC14499
0.5455	Remote Similarity	NPC4421
0.5417	Remote Similarity	NPC270590
0.5286	Remote Similarity	NPC118080
0.5263	Remote Similarity	NPC483848
0.5256	Remote Similarity	NPC212768
0.5256	Remote Similarity	NPC475122
0.5195	Remote Similarity	NPC483849
0.5143	Remote Similarity	NPC481047
0.5143	Remote Similarity	NPC481045
0.5125	Remote Similarity	NPC483865
0.5072	Remote Similarity	NPC481066
0.507	Remote Similarity	NPC607964
0.5068	Remote Similarity	NPC291599

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474608 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3992
0.1-0.2	4945
0.2-0.3	211
0.3-0.4	2
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