NPASS Compound

Natural Product: NPC469458

Natural Product ID	NPC469458
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Nudanpinoside H
IUPAC Name	n.a.
Synonyms	Nudanpinoside H
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1079224
PubChem CID	46883188
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 75 81 0 0 0 0 0 0 0 0999 V2000 -0.1504 -3.6908 0.4280 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3800 -2.8280 0.5494 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5972 -3.6757 0.9376 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7711 -2.7266 0.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7159 -1.9983 -0.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8066 -2.5441 -1.4437 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6551 -1.9695 -0.6441 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6310 -0.9503 -0.0849 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3908 -1.0390 1.3535 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2554 -1.8823 1.5542 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5328 -1.7248 1.8416 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7679 0.3030 -0.8333 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9666 0.9390 -0.6875 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 1.5105 0.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1214 1.5269 1.4797 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9629 2.1173 0.1147 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5339 2.1070 -1.1180 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7769 2.6700 -1.3439 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4242 3.2439 -0.2837 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8613 3.2628 0.9688 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6080 2.6883 1.1677 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6052 -1.5661 -1.3898 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3686 -0.8085 -0.8343 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6823 0.3631 -1.7304 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5989 1.3559 -1.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2632 0.6441 0.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5489 -0.7962 -0.1332 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5881 -1.5289 -0.7696 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9139 -0.9140 -0.8066 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8668 -0.1348 -0.1000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1843 -0.0568 -0.4881 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5337 -0.7043 -1.5039 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1656 0.7484 0.2438 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4583 0.7984 -0.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4020 1.5513 0.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0547 2.2839 1.6346 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7428 2.2268 2.0505 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8155 1.4668 1.3593 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0108 3.0442 2.3154 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5810 0.8761 1.3021 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7900 2.3647 -0.5138 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2698 -0.1534 -2.8906 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9728 -3.3343 1.1514 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1489 -3.8475 -0.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3862 -4.7231 0.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6646 -3.3193 1.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4721 -3.9888 1.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7110 -4.5559 0.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6598 -1.5371 -0.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7796 -3.6463 -1.5589 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8988 -2.0105 -2.3922 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2427 -0.1181 1.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5865 0.1930 -1.9349 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9851 1.0421 -0.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0434 1.6560 -1.9896 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2352 2.6633 -2.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4005 3.6965 -0.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3497 3.7104 1.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1621 2.7046 2.1650 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1121 -0.5660 0.1998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2600 0.8257 -2.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2901 1.7601 -1.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2580 1.1618 0.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6969 -1.2656 0.8824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2367 -1.9548 -0.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8134 -0.4480 -1.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8258 0.2566 -1.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4336 1.6129 0.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4177 2.7845 2.9361 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7943 1.4446 1.7136 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9508 2.6938 2.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0660 1.7073 1.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7940 3.1016 -1.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6640 -1.0368 -2.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7131 -3.0628 0.5681 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 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 8 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 7 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 26 40 1 0 25 41 1 0 24 42 1 0 4 43 1 0 7 2 1 0 10 2 1 0 11 4 1 0 8 5 1 0 21 16 1 0 28 23 1 0 38 33 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 3 48 1 0 5 49 1 0 6 50 1 0 6 51 1 0 9 52 1 0 12 53 1 0 12 54 1 0 17 55 1 0 18 56 1 0 19 57 1 0 20 58 1 0 21 59 1 0 23 60 1 0 24 61 1 0 25 62 1 0 26 63 1 0 27 64 1 0 29 65 1 0 29 66 1 0 34 67 1 0 35 68 1 0 37 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	HMSMTLNPCAHHGP-ADWPLSAPSA-N
Standard InCHI	InChI=1S/C30H32O13/c1-27-13-29(37)19-11-30(27,28(19,26(42-27)43-29)14-39-24(36)15-5-3-2-4-6-15)41-25-22(34)21(33)20(32)18(40-25)12-38-23(35)16-7-9-17(31)10-8-16/h2-10,18-22,25-26,31-34,37H,11-14H2,1H3/t18-,19+,20-,21+,22-,25+,26?,27+,28+,29-,30-/m1/s1
SMILES	CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)COC(=O)C7=CC=C(C=C7)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	600.18	Volume:	560.722 ? Van der Waals volume.
Dense:	1.07	LogP:	1.63 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.076 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.408 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	33.0
TPSA:	190.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	5.0	Rings:	9.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.259	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.164	Fsp³:	0.533
MCE-18:	160.435 ? 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:	0.167	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.039 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.545 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.104	Promiscuous compounds:	0.144

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.177	MDCK Permeability:	-5.213
Pgp-inhibitor:	0.015	Pgp-substrate:	0.811
PAMPA:	0.995 ? 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):	0.031
20% Bioavailability (F20%):	0.381	30% Bioavailability (F30%):	0.81
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.989
Plasma Protein Binding (PPB):	76.235%	Volume Distribution (VD):	-0.503
Fu:	39.389% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.335
OATP1B3 inhibitor:	0.982	BCRP inhibitor:	0.155
BSEP inhibitor:	0.383

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.062	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.866
HLM stability:	0.922 ? 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):

2.57

Half-life (T1/2):

1.962

ADMET: Toxicity

hERG Blockers:	0.164	hERG Blockers (10um):	0.746
Human Hepatotoxicity (H-HT):	0.061	Drug-induced Liver Injury (DILI):	0.265
AMES Toxicity:	0.437	Rat Oral Acute Toxicity:	0.236
Maximum Recommended Daily Dose:	0.624	Skin Sensitization:	0.241
Carcinogencity:	0.533	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.015
Drug-induced Neurotoxicity:	0.768	Ototoxicity:	0.839
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.055
Genotoxicity:	0.281	RPMI-8226 Immunitoxicity:	0.096
A549 Cytotoxicity:	0.051	Hek293 Cytotoxicity:	0.901
BCF:	0.706 ? 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:	3.854 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.602 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.801 ? 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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	IC50	>	50000.0	nM	PMID[22934671]

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 NPC469458 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	11445
0.1-0.2	34400
0.2-0.3	3793
0.3-0.4	167
0.4-0.5	15
0.5-0.6	8
0.6-0.7	9
0.7-0.8	0
0.8-0.85	3
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469396
1.0	High Similarity	NPC149002
0.9474	High Similarity	NPC88176
0.9079	High Similarity	NPC34066
0.9079	High Similarity	NPC190862
0.8675	High Similarity	NPC195114
0.8571	High Similarity	NPC148185
0.8554	High Similarity	NPC80360
0.8391	Intermediate Similarity	NPC188217
0.8025	Intermediate Similarity	NPC293568
0.8025	Intermediate Similarity	NPC161626
0.7882	Intermediate Similarity	NPC469398
0.7802	Intermediate Similarity	NPC477617
0.7654	Intermediate Similarity	NPC303429
0.7654	Intermediate Similarity	NPC56594
0.7473	Intermediate Similarity	NPC478828
0.7368	Intermediate Similarity	NPC469397
0.7241	Intermediate Similarity	NPC469419
0.7234	Intermediate Similarity	NPC469421
0.7053	Intermediate Similarity	NPC478829
0.6979	Remote Similarity	NPC478826
0.6979	Remote Similarity	NPC478827
0.6552	Remote Similarity	NPC469417
0.6517	Remote Similarity	NPC120012
0.6452	Remote Similarity	NPC469438
0.6437	Remote Similarity	NPC469448
0.6404	Remote Similarity	NPC469422
0.6277	Remote Similarity	NPC469418
0.6146	Remote Similarity	NPC260300
0.5889	Remote Similarity	NPC469399
0.5795	Remote Similarity	NPC478832
0.5745	Remote Similarity	NPC117943
0.5729	Remote Similarity	NPC469420
0.5426	Remote Similarity	NPC222102
0.5248	Remote Similarity	NPC265600
0.5165	Remote Similarity	NPC478831
0.5059	Remote Similarity	NPC479469

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3819
0.1-0.2	5218
0.2-0.3	111
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