NPASS Compound

Natural Product: NPC604180

Natural Product ID	NPC604180
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BTLJUKNIXFTSMI-DFWJFPTDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL225816
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 84 88 0 0 0 0 0 0 0 0999 V2000 6.4049 -0.9821 -0.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2373 0.4588 0.2517 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0623 1.0091 0.2595 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6994 0.5811 0.0627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2249 -0.7731 -0.1873 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5296 -1.7863 0.8780 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.8301 -0.5902 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4537 -2.3025 -0.8437 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1009 -2.5480 -0.2114 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4701 -1.1557 -0.2554 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7478 -0.8428 -1.6867 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6377 -0.9341 0.6202 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6580 -1.9866 0.2808 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0557 -1.6109 0.6656 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3986 -0.3954 -0.1687 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8428 -0.0418 -0.0703 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5774 -0.7814 1.0166 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5848 -0.3498 -1.3770 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0482 1.4504 0.1806 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7410 1.8134 1.4725 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2616 2.1912 -0.8534 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7873 1.9337 -0.7037 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4900 0.7266 0.1625 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1202 0.9454 1.5628 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1011 0.4641 0.4726 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0864 1.4540 0.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3269 1.1066 0.1289 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7181 -0.3348 0.3116 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8242 -0.5922 1.7645 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5005 1.2860 0.5284 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1329 2.6282 1.0259 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4440 1.2644 -0.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8072 -1.2819 -0.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4743 -1.0773 -0.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3156 -1.6361 0.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1564 2.1546 0.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3143 1.3020 -0.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0330 0.9873 0.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6979 -1.1522 -1.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6425 -2.3102 1.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1704 -2.6451 0.5136 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1073 -1.3217 1.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7082 -0.2568 -1.5556 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2365 -2.9884 -0.5389 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3677 -2.4361 -1.9657 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1264 -3.0340 0.7487 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4808 -3.1762 -0.9502 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5395 -1.7156 -2.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8491 -0.6545 -1.8736 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2040 -0.0080 -2.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4012 -1.1028 1.6947 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6455 -2.1999 -0.8087 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4015 -2.9450 0.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2065 -1.4624 1.7347 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7226 -2.4335 0.3357 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1921 -0.6956 -1.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6324 -0.3989 1.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6532 -1.8730 0.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1766 -0.5548 2.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9002 -0.1439 -2.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8102 -1.4340 -1.4260 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4622 0.2891 -1.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1329 1.6333 -0.0312 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4604 2.4313 1.8049 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4155 3.2959 -0.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6556 1.9372 -1.8538 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2710 2.8000 -0.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3916 1.6870 -1.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9611 2.0131 1.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2936 0.2499 2.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2985 2.4206 0.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3385 1.7819 -1.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7678 1.6950 0.9897 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8917 1.4761 -0.7645 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7772 -0.3749 2.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5173 -1.5948 2.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0923 0.0963 2.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9614 0.7314 1.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7654 3.3398 0.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0931 3.1057 1.3996 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5033 2.5566 1.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1708 0.4411 -0.4757 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9385 1.2021 -1.6109 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0524 2.2150 -0.5667 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 16 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 23 22 1 6 23 24 1 0 25 24 1 1 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 2 30 1 0 30 31 1 0 30 32 1 0 28 7 1 0 28 10 1 0 25 12 1 0 23 15 1 0 25 23 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 6 6 40 1 0 6 41 1 0 6 42 1 0 7 43 1 6 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 1 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 6 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 18 62 1 0 19 63 1 6 20 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 24 69 1 0 24 70 1 0 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 32 83 1 0 32 84 1 0 M END

Standard InCHIKey	BTLJUKNIXFTSMI-DFWJFPTDSA-N
Standard InCHI	InChI=1S/C31H52O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h9,20,22-26,32H,10-19H2,1-8H3/b21-9+/t22-,23-,24+,25+,26+,28-,29+,30-,31+/m1/s1
SMILES	C/C(=CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.4	Volume:	508.103 ? Van der Waals volume.
Dense:	0.867	LogP:	5.997 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.344 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.826 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.435	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.536	Fsp³:	0.935
MCE-18:	133.2 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.948	Fluc inhibitor:	0.001 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.688	Promiscuous compounds:	0.078

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.133	MDCK Permeability:	-4.856
Pgp-inhibitor:	0.625	Pgp-substrate:	0.034
PAMPA:	0.151 ? 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):	0.001
20% Bioavailability (F20%):	0.188	30% Bioavailability (F30%):	0.224
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17	MRP1:	0.07
Plasma Protein Binding (PPB):	94.786%	Volume Distribution (VD):	0.005
Fu:	6.224% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.981
BSEP inhibitor:	0.88

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.272
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.673
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.336
CYP2D6-inhibitor:	0.416	CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.701
HLM stability:	0.996 ? 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):

14.576

Half-life (T1/2):

0.557

ADMET: Toxicity

hERG Blockers:	0.104	hERG Blockers (10um):	0.438
Human Hepatotoxicity (H-HT):	0.591	Drug-induced Liver Injury (DILI):	0.029
AMES Toxicity:	0.119	Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.505	Skin Sensitization:	0.875
Carcinogencity:	0.617	Eye Corrosion:	0.002
Eye Irritation:	0.267	Respiratory Toxicity:	0.949
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.716
Hematotoxicity:	0.367	Drug-induced Nephrotoxicity:	0.504
Genotoxicity:	0.186	RPMI-8226 Immunitoxicity:	0.078
A549 Cytotoxicity:	0.31	Hek293 Cytotoxicity:	0.398
BCF:	3.401 ? 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:	5.197 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.966 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.414 ? 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
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27807	Calotropis procera	Species	Apocynaceae	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
Inhibition	4
Activity	2
IC50	1

Activity Type	# Activity
Cell line	1
Organism	5
Unchecked	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17503850]
NPT29358	Organism	Human gammaherpesvirus 4	Human gammaherpesvirus 4	Inhibition	=	72.8	%	PMID[17503850]
NPT29358	Organism	Human gammaherpesvirus 4	Human gammaherpesvirus 4	Inhibition	=	95.2	%	PMID[17503850]
NPT29358	Organism	Human gammaherpesvirus 4	Human gammaherpesvirus 4	Inhibition	=	31.4	%	PMID[17503850]
NPT29358	Organism	Human gammaherpesvirus 4	Human gammaherpesvirus 4	Inhibition	=	0.0	%	PMID[17503850]
NPT28438	Unchecked	Unchecked	n.a.	Activity	=	2.0	n.a.	PMID[17503850]
NPT29358	Organism	Human gammaherpesvirus 4	Human gammaherpesvirus 4	IC50	=	9.9	nM	PMID[17503850]

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 NPC604180 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	24479
0.1-0.2	21360
0.2-0.3	3391
0.3-0.4	487
0.4-0.5	92
0.5-0.6	19
0.6-0.7	20
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	Natural Product ID
0.7551	Intermediate Similarity	NPC85346
0.7551	Intermediate Similarity	NPC65897
0.7551	Intermediate Similarity	NPC80237
0.72	Intermediate Similarity	NPC254509
0.72	Intermediate Similarity	NPC82623
0.7143	Intermediate Similarity	NPC607543
0.7	Intermediate Similarity	NPC331618
0.7	Intermediate Similarity	NPC257191
0.7	Intermediate Similarity	NPC196358
0.6939	Remote Similarity	NPC41577
0.6923	Remote Similarity	NPC22133
0.6863	Remote Similarity	NPC200243
0.6852	Remote Similarity	NPC89747
0.68	Remote Similarity	NPC299948
0.68	Remote Similarity	NPC241085
0.6731	Remote Similarity	NPC472342
0.6731	Remote Similarity	NPC195530
0.6607	Remote Similarity	NPC18384
0.6545	Remote Similarity	NPC134481
0.6481	Remote Similarity	NPC76518
0.6415	Remote Similarity	NPC470830
0.6415	Remote Similarity	NPC479659
0.6415	Remote Similarity	NPC273366
0.6296	Remote Similarity	NPC70982
0.6182	Remote Similarity	NPC67872
0.6182	Remote Similarity	NPC472341
0.6071	Remote Similarity	NPC12722
0.6034	Remote Similarity	NPC110923
0.6034	Remote Similarity	NPC74296
0.5965	Remote Similarity	NPC473238
0.5932	Remote Similarity	NPC307776
0.5932	Remote Similarity	NPC483817
0.5833	Remote Similarity	NPC195366
0.5833	Remote Similarity	NPC85379
0.5833	Remote Similarity	NPC144909
0.5833	Remote Similarity	NPC476304
0.5833	Remote Similarity	NPC114743
0.5763	Remote Similarity	NPC476186
0.5714	Remote Similarity	NPC473279
0.5714	Remote Similarity	NPC302041
0.569	Remote Similarity	NPC606508
0.5439	Remote Similarity	NPC49168
0.5439	Remote Similarity	NPC5046
0.5345	Remote Similarity	NPC113978
0.5263	Remote Similarity	NPC145552
0.5254	Remote Similarity	NPC195489
0.5085	Remote Similarity	NPC269058
0.5085	Remote Similarity	NPC71520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC604180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7991
0.1-0.2	1105
0.2-0.3	52
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