NPASS Compound

Natural Product: NPC489800

Natural Product ID	NPC489800
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YENKFKJTSHOLIL-IWRNXBKVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 89 0 0 0 0 0 0 0 0999 V2000 7.2669 1.2285 -0.9686 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7100 0.8139 0.3284 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8702 -0.1630 0.4976 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3627 -0.9855 -0.5995 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 -0.9529 -0.4996 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2909 0.4173 -0.6338 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6343 0.9382 -2.0005 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0333 0.7588 -0.0443 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7609 2.3174 -0.2487 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4569 2.4847 0.5216 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0747 1.0840 0.7000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3807 0.6094 2.0617 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5106 0.9543 0.5411 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0176 -0.1103 -0.0550 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2113 -1.2113 -0.5838 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2649 -1.0423 -0.4576 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6822 0.3598 -0.4295 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1770 1.0404 -1.7036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4991 -0.1477 -0.1965 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8734 0.9615 -1.1732 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8920 -1.4671 -0.8104 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3997 -1.6131 -0.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7516 -1.6555 0.7052 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4682 -0.3469 1.3863 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6310 -0.6032 2.8925 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5553 0.6051 1.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0839 0.0858 1.1510 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8312 1.5432 1.4924 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4552 1.9375 1.0456 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 3.1341 1.1306 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9378 -2.6717 1.2582 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2991 -1.9141 -1.3672 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8347 -3.1548 -0.9164 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -3.3586 0.3018 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3150 -4.1106 -1.9111 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1216 1.5479 1.5455 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7052 1.2719 2.6881 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0110 2.5887 1.4016 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2919 1.6513 -0.7968 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3300 0.3602 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6001 1.9898 -1.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5288 -0.3743 1.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5902 -2.0561 -0.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7170 -0.7697 -1.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6515 -1.3239 0.5492 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0649 1.0269 0.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4008 1.9712 -2.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7116 0.8054 -2.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1695 0.3104 -2.8197 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1174 0.7230 1.0665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6991 2.5473 -1.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5926 2.8594 0.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2149 3.1913 0.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6913 2.9249 1.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7870 -0.3965 2.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5635 0.5516 2.6876 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9862 1.3651 2.6055 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4896 -2.1740 -0.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5295 -1.4190 -1.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6503 -1.5637 -1.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6334 -1.6785 0.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 0.3933 -2.1846 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3557 1.9852 -1.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9512 1.0924 -2.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0444 1.6931 -1.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7488 1.5434 -0.8291 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1399 0.5045 -2.1525 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4748 -2.3469 -0.3236 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5552 -1.4532 -1.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8596 -0.7840 -1.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7008 -2.5624 -1.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8129 -1.9043 0.7870 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7183 -1.1478 3.2659 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7988 0.3431 3.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4817 -1.2934 3.0557 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8088 0.5689 -0.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4392 1.6296 1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4976 0.2238 1.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4295 -0.4861 1.8796 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8461 1.6698 2.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5259 2.2503 1.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0671 -3.5069 0.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2264 -4.0846 -1.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7454 -3.9420 -2.9198 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6351 -5.1518 -1.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4394 3.0697 2.1839 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 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 14 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 23 31 1 0 5 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 2 36 1 0 36 37 2 0 36 38 1 0 17 8 1 0 27 19 1 0 17 11 1 0 29 13 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 1 6 46 1 1 7 47 1 0 7 48 1 0 7 49 1 0 8 50 1 1 9 51 1 0 9 52 1 0 10 53 1 0 10 54 1 0 12 55 1 0 12 56 1 0 12 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 18 62 1 0 18 63 1 0 18 64 1 0 20 65 1 0 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 23 72 1 6 25 73 1 0 25 74 1 0 25 75 1 0 26 76 1 0 26 77 1 0 26 78 1 0 27 79 1 1 28 80 1 0 28 81 1 0 31 82 1 0 35 83 1 0 35 84 1 0 35 85 1 0 38 86 1 0 M END

Standard InCHIKey	YENKFKJTSHOLIL-IWRNXBKVSA-N
Standard InCHI	InChI=1S/C32H48O6/c1-18(28(36)37)9-10-24(38-20(3)33)19(2)21-11-16-32(8)27-22(12-15-31(21,32)7)30(6)14-13-26(35)29(4,5)25(30)17-23(27)34/h9,19,21,24-26,35H,10-17H2,1-8H3,(H,36,37)/b18-9+/t19-,21+,24-,25-,26+,30+,31+,32-/m0/s1
SMILES	C/C(=CC[C@@H]([C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](C(C)(C)[C@@H]1CC3=O)O)OC(=O)C)/C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.35	Volume:	567.361 ? Van der Waals volume.
Dense:	0.931	LogP:	2.878 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.798 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.088 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	100.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.311	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.022	Fsp³:	0.781
MCE-18:	87.193 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.924	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? 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:	0.325	Promiscuous compounds:	0.304

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.33	MDCK Permeability:	-5.024
Pgp-inhibitor:	0.926	Pgp-substrate:	0.01
PAMPA:	0.858 ? 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):	0.021
20% Bioavailability (F20%):	0.77	30% Bioavailability (F30%):	0.843
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.974
Plasma Protein Binding (PPB):	84.793%	Volume Distribution (VD):	-0.421
Fu:	13.302% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.005
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.214	CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.858	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.695
HLM stability:	0.942 ? 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):

6.629

Half-life (T1/2):

0.784

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.733	Drug-induced Liver Injury (DILI):	0.371
AMES Toxicity:	0.122	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.192	Skin Sensitization:	0.996
Carcinogencity:	0.588	Eye Corrosion:	0.028
Eye Irritation:	0.743	Respiratory Toxicity:	0.4
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.819
Hematotoxicity:	0.47	Drug-induced Nephrotoxicity:	0.928
Genotoxicity:	0.391	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.036	Hek293 Cytotoxicity:	0.061
BCF:	0.608 ? 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:	3.615 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.46 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.632 ? 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
NPO40519	Ganoderma orbiforme BCC 22325	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40520	Ganoderma sp. BCC 60695	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40518	Ganoderma australe BCC 22314	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]

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	1

Activity Type	# Activity
Cell line	1
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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	95000.0	nM	PMID[28504879]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[28504879]

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 NPC489800 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	16720
0.1-0.2	25856
0.2-0.3	6629
0.3-0.4	500
0.4-0.5	89
0.5-0.6	37
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC489808
0.7714	Intermediate Similarity	NPC489807
0.7714	Intermediate Similarity	NPC478297
0.7714	Intermediate Similarity	NPC478298
0.7391	Intermediate Similarity	NPC601194
0.7162	Intermediate Similarity	NPC482571
0.6712	Remote Similarity	NPC141401
0.6533	Remote Similarity	NPC478301
0.641	Remote Similarity	NPC478309
0.6377	Remote Similarity	NPC482423
0.6282	Remote Similarity	NPC489795
0.6267	Remote Similarity	NPC69982
0.6197	Remote Similarity	NPC259286
0.6197	Remote Similarity	NPC83216
0.6197	Remote Similarity	NPC484085
0.6056	Remote Similarity	NPC275740
0.6056	Remote Similarity	NPC482424
0.6056	Remote Similarity	NPC86319
0.6027	Remote Similarity	NPC69454
0.5915	Remote Similarity	NPC110021
0.5915	Remote Similarity	NPC482426
0.5909	Remote Similarity	NPC482425
0.5875	Remote Similarity	NPC478311
0.5789	Remote Similarity	NPC482518
0.5769	Remote Similarity	NPC489791
0.575	Remote Similarity	NPC489788
0.575	Remote Similarity	NPC299325
0.5696	Remote Similarity	NPC58410
0.5676	Remote Similarity	NPC486193
0.5676	Remote Similarity	NPC183283
0.5663	Remote Similarity	NPC241221
0.5663	Remote Similarity	NPC482570
0.5542	Remote Similarity	NPC76162
0.5422	Remote Similarity	NPC489797
0.5422	Remote Similarity	NPC478304
0.5422	Remote Similarity	NPC231673
0.5412	Remote Similarity	NPC478310
0.5375	Remote Similarity	NPC478312
0.5375	Remote Similarity	NPC478300
0.5366	Remote Similarity	NPC478299
0.5357	Remote Similarity	NPC482566
0.5325	Remote Similarity	NPC8571
0.5294	Remote Similarity	NPC489794
0.5256	Remote Similarity	NPC484971
0.5256	Remote Similarity	NPC484970
0.525	Remote Similarity	NPC276127
0.525	Remote Similarity	NPC478307
0.5238	Remote Similarity	NPC489799
0.5233	Remote Similarity	NPC489809
0.5176	Remote Similarity	NPC482565
0.5132	Remote Similarity	NPC20388
0.5125	Remote Similarity	NPC11903
0.5062	Remote Similarity	NPC489801
0.5059	Remote Similarity	NPC166120
0.5057	Remote Similarity	NPC482569
0.5057	Remote Similarity	NPC146822

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5537
0.1-0.2	3434
0.2-0.3	173
0.3-0.4	6
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