NPASS Compound

Natural Product: NPC40888

Natural Product ID	NPC40888
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HCISIQALOMLBND-LLUAOXPXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10576408
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 81 85 0 0 0 0 0 0 0 0999 V2000 5.6931 -2.3046 -0.4159 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1517 -0.9123 -0.6594 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4993 -0.5482 -2.0911 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6250 -1.0298 -0.5900 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9889 0.3421 -0.5204 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5125 0.1153 -0.5032 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8811 -0.0149 -1.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5736 -0.2418 -1.8116 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2925 -0.3333 -0.4914 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7560 -0.3376 -0.6865 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1360 0.3879 -1.9332 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2190 -1.7870 -0.9796 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4937 -2.1635 -0.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5018 -1.1215 -0.0710 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9469 0.1529 0.5012 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3743 0.3049 1.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4304 1.3919 -0.1862 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4599 0.0055 0.5613 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8702 1.1627 1.3221 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4295 0.8199 1.7340 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6422 0.6101 0.4506 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3997 1.9996 -0.0921 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7319 0.0225 0.7549 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6271 -1.4687 1.0566 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4269 0.6666 1.9129 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4777 1.6679 1.5549 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5024 1.2248 0.5433 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6686 0.6184 1.2903 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6696 0.0753 0.3341 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2479 -0.3157 2.2347 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0097 2.4909 -0.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1705 2.9079 0.0906 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1285 3.2357 -0.8226 O 0 0 0 0 0 1 0 0 0 0 0 0 -6.4054 -0.8880 -1.1367 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1248 -3.0232 -1.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5862 -2.6585 0.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7556 -2.3742 -0.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2766 0.2634 -2.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9567 -1.3970 -2.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6006 -0.2589 -2.6782 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3457 -1.5279 -1.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 -1.6440 0.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2227 0.8010 -1.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4199 0.0388 -2.6206 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7469 -1.1721 -2.3933 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9251 0.6607 -2.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0507 -1.3731 -0.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2167 0.3698 -2.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7008 -0.2237 -2.7867 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7929 1.3975 -2.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1991 -2.0044 -2.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4074 -2.4604 -0.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9949 -2.9179 -1.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3117 -2.7698 0.5729 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1911 -1.5572 0.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4617 1.3751 2.2439 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7474 -0.2868 2.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4329 -0.0900 1.9866 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1555 1.1592 -1.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0439 2.0676 0.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6054 2.0637 -0.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2959 -0.8813 1.2588 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9397 2.1236 0.8227 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4275 1.2365 2.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4207 -0.0301 2.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0957 1.7914 2.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2895 2.6723 0.8174 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5261 2.1399 -0.6417 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2888 2.4506 -0.5820 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2473 -1.7155 1.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4980 -1.6955 1.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8025 -2.1094 0.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7553 1.1557 2.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9440 -0.1210 2.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0506 1.9014 2.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0558 2.6548 1.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1674 1.4971 1.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2102 0.9058 -0.1729 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4552 -0.4578 0.9475 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8371 -1.0972 2.2671 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0387 -1.6150 -1.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 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 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 6 31 32 2 0 31 33 1 0 14 34 1 0 29 2 1 0 27 5 1 0 23 6 1 0 21 9 1 0 18 10 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 6 7 44 1 0 8 45 1 0 8 46 1 0 9 47 1 1 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 1 16 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 1 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 22 67 1 0 22 68 1 0 22 69 1 0 24 70 1 0 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 28 77 1 1 29 78 1 0 29 79 1 0 30 80 1 0 34 81 1 0 M CHG 1 33 -1 M END

Standard InCHIKey	HCISIQALOMLBND-LLUAOXPXSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-25(2)16-19-18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-29(21,7)28(18,6)14-15-30(19,24(33)34)23(32)17-25/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/p-1/t19-,20-,21+,22-,23-,27-,28+,29+,30-/m0/s1
SMILES	CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]2([C@H](C1)O)C(=O)[O-])O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.872 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.759 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.939 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.397	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.797	Fsp³:	0.9
MCE-18:	108.07 ? 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:	0.646	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.361	Promiscuous compounds:	0.084

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.498	MDCK Permeability:	-5.09
Pgp-inhibitor:	0.005	Pgp-substrate:	0.014
PAMPA:	1.0 ? 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):	0.005
20% Bioavailability (F20%):	0.699	30% Bioavailability (F30%):	0.102
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.777	MRP1:	0.95
Plasma Protein Binding (PPB):	92.533%	Volume Distribution (VD):	-0.354
Fu:	6.679% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.934	BCRP inhibitor:	0.049
BSEP inhibitor:	0.837

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.031	CYP2C19-substrate:	0.454
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.148
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.047
HLM stability:	0.142 ? 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):

4.412

Half-life (T1/2):

1.015

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.058
Human Hepatotoxicity (H-HT):	0.671	Drug-induced Liver Injury (DILI):	0.531
AMES Toxicity:	0.344	Rat Oral Acute Toxicity:	0.576
Maximum Recommended Daily Dose:	0.483	Skin Sensitization:	0.961
Carcinogencity:	0.949	Eye Corrosion:	0.054
Eye Irritation:	0.699	Respiratory Toxicity:	0.936
Drug-induced Neurotoxicity:	0.07	Ototoxicity:	0.593
Hematotoxicity:	0.583	Drug-induced Nephrotoxicity:	0.941
Genotoxicity:	0.78	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.368	Hek293 Cytotoxicity:	0.237
BCF:	1.354 ? 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:	3.879 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.474 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.777 ? 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
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10980	Petasites japonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10980	Petasites japonicus	Species	Asteraceae	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

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

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 NPC40888 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	23879
0.1-0.2	22159
0.2-0.3	2898
0.3-0.4	635
0.4-0.5	204
0.5-0.6	64
0.6-0.7	15
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
0.6866	Remote Similarity	NPC480946
0.6866	Remote Similarity	NPC130577
0.6866	Remote Similarity	NPC142415
0.6866	Remote Similarity	NPC102683
0.6571	Remote Similarity	NPC228784
0.6571	Remote Similarity	NPC324341
0.6571	Remote Similarity	NPC601810
0.6286	Remote Similarity	NPC182797
0.6286	Remote Similarity	NPC306541
0.6286	Remote Similarity	NPC52169
0.6286	Remote Similarity	NPC195019
0.6286	Remote Similarity	NPC488562
0.6286	Remote Similarity	NPC606443
0.6143	Remote Similarity	NPC187722
0.6056	Remote Similarity	NPC290972
0.589	Remote Similarity	NPC202728
0.589	Remote Similarity	NPC158059
0.589	Remote Similarity	NPC293564
0.5833	Remote Similarity	NPC270768
0.5833	Remote Similarity	NPC59263
0.5833	Remote Similarity	NPC210106
0.5833	Remote Similarity	NPC51700
0.5833	Remote Similarity	NPC88716
0.5833	Remote Similarity	NPC68160
0.5833	Remote Similarity	NPC112866
0.5823	Remote Similarity	NPC603645
0.5775	Remote Similarity	NPC477872
0.5694	Remote Similarity	NPC198664
0.5676	Remote Similarity	NPC145667
0.5676	Remote Similarity	NPC298554
0.5616	Remote Similarity	NPC171203
0.5616	Remote Similarity	NPC84319
0.5616	Remote Similarity	NPC307426
0.5616	Remote Similarity	NPC98442
0.5616	Remote Similarity	NPC52021
0.5616	Remote Similarity	NPC242468
0.5616	Remote Similarity	NPC599947
0.5522	Remote Similarity	NPC290598
0.5522	Remote Similarity	NPC30590
0.5513	Remote Similarity	NPC474727
0.5507	Remote Similarity	NPC311078
0.5479	Remote Similarity	NPC96916
0.5467	Remote Similarity	NPC29765
0.5455	Remote Similarity	NPC222047
0.5429	Remote Similarity	NPC235341
0.5405	Remote Similarity	NPC7260
0.5405	Remote Similarity	NPC210037
0.5405	Remote Similarity	NPC120968
0.5405	Remote Similarity	NPC121798
0.5405	Remote Similarity	NPC64872
0.5405	Remote Similarity	NPC25906
0.5405	Remote Similarity	NPC234346
0.5405	Remote Similarity	NPC227467
0.5405	Remote Similarity	NPC273621
0.5294	Remote Similarity	NPC27765
0.5294	Remote Similarity	NPC122418
0.5294	Remote Similarity	NPC491014
0.5286	Remote Similarity	NPC101475
0.5286	Remote Similarity	NPC34177
0.527	Remote Similarity	NPC610937
0.5211	Remote Similarity	NPC253807
0.5211	Remote Similarity	NPC158662
0.5205	Remote Similarity	NPC246708
0.52	Remote Similarity	NPC282616
0.52	Remote Similarity	NPC229281
0.5135	Remote Similarity	NPC267691
0.5132	Remote Similarity	NPC231063
0.5132	Remote Similarity	NPC18872
0.5132	Remote Similarity	NPC282395
0.5132	Remote Similarity	NPC290614
0.5132	Remote Similarity	NPC472149
0.5132	Remote Similarity	NPC300351
0.5132	Remote Similarity	NPC110308
0.5128	Remote Similarity	NPC130520
0.5072	Remote Similarity	NPC120098
0.5068	Remote Similarity	NPC480950
0.5067	Remote Similarity	NPC274330
0.5067	Remote Similarity	NPC172361
0.5065	Remote Similarity	NPC136697

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC40888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7238
0.1-0.2	1870
0.2-0.3	35
0.3-0.4	4
0.4-0.5	3
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