NPASS Compound

Natural Product: NPC483845

Natural Product ID	NPC483845
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SYMROPCAWOJPQD-SPIKHJKTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101880840
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 3D 86 90 0 0 0 0 0 0 0 0999 V2000 -1.1739 -4.1038 -0.7424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6903 -3.7044 0.6107 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7738 -3.9106 1.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4051 -2.7315 2.2272 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5239 -1.5120 2.2685 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8518 -1.2260 0.9206 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9924 -1.1142 -0.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6640 -0.8493 -1.3544 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5381 -0.7091 -2.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7720 -0.8236 -2.1609 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1311 -0.4221 -3.7888 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1373 0.0862 0.9456 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3350 0.1007 0.7643 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9791 -1.2034 0.4939 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0244 -2.1008 -0.3263 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0589 -2.4183 0.6918 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7974 -2.5119 1.9051 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0255 -2.0080 1.7694 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4251 -1.2096 2.9878 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1276 -3.0728 1.6496 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6409 -2.9492 -1.1605 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7978 -3.0727 -2.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2518 -2.2039 -3.1272 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5584 -4.1529 -3.1029 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7342 1.1533 -0.1013 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4658 2.2594 0.2425 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7919 2.3076 1.4388 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8624 3.3203 -0.6525 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5417 3.3435 -1.9934 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9521 4.3893 -2.7965 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6973 5.4405 -2.2691 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0233 5.4320 -0.9414 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5997 4.3744 -0.1635 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6953 0.9860 -0.0246 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3974 2.1303 0.2869 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5452 2.3802 1.5068 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9637 3.0431 -0.6869 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8568 2.8577 -2.0484 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4350 3.7909 -2.8831 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1138 4.8988 -2.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2239 5.0895 -1.0397 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6407 4.1481 -0.2241 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1129 -0.3911 2.8187 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7681 0.2299 3.9753 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8275 -0.2667 4.5972 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4557 1.4193 4.4762 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8775 -5.1533 -1.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3032 -4.1754 -0.7327 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9175 -3.4738 -1.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0827 -4.5024 0.8644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4770 -4.6074 2.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6131 -4.5262 1.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4191 -2.5261 1.8006 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6672 -2.9196 3.3172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7064 -1.7739 2.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7151 -1.9338 -0.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5747 -0.2059 0.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6169 0.5048 -4.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5487 -1.2445 -4.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0385 -0.4284 -3.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4338 0.5758 1.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7824 0.4466 1.7493 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9724 -1.1790 0.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5667 -1.3700 -1.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7130 -1.9899 3.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6210 -0.6489 3.4490 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3626 -0.6384 2.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5598 -4.0287 1.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8409 -2.8397 0.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6715 -3.2343 2.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0796 -4.3447 -4.1078 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6084 -3.8843 -3.3324 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4720 -5.1133 -2.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9608 2.5059 -2.3621 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7064 4.4104 -3.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0224 6.2658 -2.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6039 6.2640 -0.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8875 4.4165 0.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3256 1.9909 -2.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3604 3.6607 -3.9701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5708 5.6364 -3.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7501 5.9488 -0.6162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7493 4.3340 0.8563 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7010 2.1741 4.7998 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0458 1.1781 5.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1032 1.9158 3.7364 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 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 17 18 1 0 18 19 1 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 13 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 12 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 5 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 16 2 1 0 33 28 1 0 42 37 1 0 16 6 1 0 18 14 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 1 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 1 7 56 1 0 7 57 1 0 11 58 1 0 11 59 1 0 11 60 1 0 12 61 1 1 13 62 1 1 14 63 1 6 15 64 1 6 19 65 1 0 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 20 70 1 0 24 71 1 0 24 72 1 0 24 73 1 0 29 74 1 0 30 75 1 0 31 76 1 0 32 77 1 0 33 78 1 0 38 79 1 0 39 80 1 0 40 81 1 0 41 82 1 0 42 83 1 0 46 84 1 0 46 85 1 0 46 86 1 0 M END

Standard InCHIKey	SYMROPCAWOJPQD-SPIKHJKTSA-N
Standard InCHI	InChI=1S/C35H40O11/c1-20-17-18-26(42-22(3)37)34(19-41-21(2)36)30(45-32(40)25-15-11-8-12-16-25)28(44-31(39)24-13-9-7-10-14-24)27-29(43-23(4)38)35(20,34)46-33(27,5)6/h7-16,20,26-30H,17-19H2,1-6H3/t20-,26+,27-,28-,29-,30-,34+,35-/m1/s1
SMILES	C[C@@H]1CC[C@@H]([C@@]2(COC(=O)C)[C@@H]([C@@H]([C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.26	Volume:	638.825 ? Van der Waals volume.
Dense:	0.996	LogP:	2.848 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.832 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.405 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	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:	0.3	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.744	Fsp³:	0.514
MCE-18:	163.358 ? 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:	0.548	Fluc inhibitor:	0.049 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.157 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.209	Promiscuous compounds:	0.029

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212	MDCK Permeability:	-4.651
Pgp-inhibitor:	1.0	Pgp-substrate:	0.455
PAMPA:	0.211 ? 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%):	0.388
50% Bioavailability (F50%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094	MRP1:	1.0
Plasma Protein Binding (PPB):	90.792%	Volume Distribution (VD):	-0.501
Fu:	10.054% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.508
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.883
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.397
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.007
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):

4.472

Half-life (T1/2):

0.427

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.482
Human Hepatotoxicity (H-HT):	0.277	Drug-induced Liver Injury (DILI):	0.667
AMES Toxicity:	0.419	Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.135	Skin Sensitization:	0.875
Carcinogencity:	0.458	Eye Corrosion:	0.003
Eye Irritation:	0.205	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.112	Ototoxicity:	0.288
Hematotoxicity:	0.132	Drug-induced Nephrotoxicity:	0.556
Genotoxicity:	0.653	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.092	Hek293 Cytotoxicity:	0.142
BCF:	0.915 ? 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:	4.033 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.781 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.388 ? 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]

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
Activity	5
FC	2
Inhibition	1

Activity Type	# Activity
Cell line	1
Others	5
Non-molecular	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[26854381]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	FC	=	2.1	n.a.	PMID[27120798]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	21.2	%	PMID[27120798]
NPT2	Others	Unspecified	n.a.	Activity	=	36.1	%	PMID[26854381]
NPT2	Others	Unspecified	n.a.	Activity	=	7.5	%	PMID[26854381]
NPT2	Others	Unspecified	n.a.	Activity	=	78.5	%	PMID[26854381]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[26854381]
NPT2	Others	Unspecified	n.a.	FC	=	131.0	n.a.	PMID[27120798]

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 NPC483845 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	13622
0.1-0.2	33895
0.2-0.3	1729
0.3-0.4	433
0.4-0.5	98
0.5-0.6	43
0.6-0.7	17
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC90257
0.9333	High Similarity	NPC69357
0.8923	High Similarity	NPC483849
0.8889	High Similarity	NPC483844
0.8485	Intermediate Similarity	NPC483848
0.7778	Intermediate Similarity	NPC211137
0.75	Intermediate Similarity	NPC475429
0.7463	Intermediate Similarity	NPC137718
0.7463	Intermediate Similarity	NPC148062
0.7432	Intermediate Similarity	NPC473115
0.7424	Intermediate Similarity	NPC51314
0.7313	Intermediate Similarity	NPC147880
0.7231	Intermediate Similarity	NPC66761
0.7231	Intermediate Similarity	NPC483843
0.7206	Intermediate Similarity	NPC483842
0.7164	Intermediate Similarity	NPC17877
0.7143	Intermediate Similarity	NPC252314
0.697	Remote Similarity	NPC476094
0.6912	Remote Similarity	NPC473060
0.68	Remote Similarity	NPC479040
0.6761	Remote Similarity	NPC306146
0.6761	Remote Similarity	NPC483841
0.6667	Remote Similarity	NPC479043
0.6667	Remote Similarity	NPC481059
0.662	Remote Similarity	NPC473758
0.662	Remote Similarity	NPC473088
0.6479	Remote Similarity	NPC147217
0.6338	Remote Similarity	NPC48017
0.625	Remote Similarity	NPC483846
0.6111	Remote Similarity	NPC246480
0.6	Remote Similarity	NPC57628
0.6	Remote Similarity	NPC11685
0.6	Remote Similarity	NPC488902
0.6	Remote Similarity	NPC488903
0.5949	Remote Similarity	NPC488900
0.5949	Remote Similarity	NPC488899
0.589	Remote Similarity	NPC4341
0.589	Remote Similarity	NPC479047
0.589	Remote Similarity	NPC291638
0.5833	Remote Similarity	NPC241951
0.5833	Remote Similarity	NPC90614
0.5714	Remote Similarity	NPC474608
0.5676	Remote Similarity	NPC191082
0.5658	Remote Similarity	NPC479044
0.5625	Remote Similarity	NPC4421
0.5584	Remote Similarity	NPC472569
0.5584	Remote Similarity	NPC16912
0.5556	Remote Similarity	NPC481047
0.5556	Remote Similarity	NPC481045
0.5526	Remote Similarity	NPC254558
0.5526	Remote Similarity	NPC471107
0.5493	Remote Similarity	NPC283375
0.5493	Remote Similarity	NPC183122
0.5455	Remote Similarity	NPC41481
0.5432	Remote Similarity	NPC212768
0.5405	Remote Similarity	NPC483847
0.5385	Remote Similarity	NPC472570
0.5333	Remote Similarity	NPC483902
0.5325	Remote Similarity	NPC171207
0.5325	Remote Similarity	NPC471100
0.5325	Remote Similarity	NPC605884
0.5316	Remote Similarity	NPC184747
0.5309	Remote Similarity	NPC481486
0.5238	Remote Similarity	NPC6576
0.52	Remote Similarity	NPC475759
0.52	Remote Similarity	NPC470152
0.52	Remote Similarity	NPC483862
0.5195	Remote Similarity	NPC139067
0.5195	Remote Similarity	NPC43241
0.519	Remote Similarity	NPC609924
0.5185	Remote Similarity	NPC481489
0.5132	Remote Similarity	NPC281717
0.5132	Remote Similarity	NPC472577
0.5122	Remote Similarity	NPC481488
0.5067	Remote Similarity	NPC118080
0.5065	Remote Similarity	NPC163719
0.5065	Remote Similarity	NPC95810

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3515
0.1-0.2	5441
0.2-0.3	194
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