NPASS Compound

Natural Product: NPC222047

Natural Product ID	NPC222047
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Quillaic Acid
IUPAC Name	(4aR,5R,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Quillaic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL260060
PubChem CID	101810
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 -3.2574 0.7144 3.7316 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3316 0.7585 3.1677 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4958 0.6295 1.6789 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1574 1.9652 1.2964 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4632 -0.4573 1.3579 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5474 0.0387 0.5879 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8992 -1.6979 0.8045 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4584 -1.7168 0.4141 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9561 -0.3586 -0.1084 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1691 0.5448 1.0662 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5835 1.8871 0.7127 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1063 1.6889 0.6017 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7065 0.7601 -0.5638 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4633 -0.4888 -0.2616 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0105 -1.5926 -1.1310 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4149 -1.8184 -0.7149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2440 -0.8403 -0.4751 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7693 0.5450 -0.6116 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3772 1.5525 0.3381 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4442 0.9527 -1.9426 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6347 0.1751 -2.3072 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5524 1.0699 -2.9342 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4381 -0.5841 -1.3178 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6567 -1.1602 -0.1591 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1209 -0.9041 1.2097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5513 -0.5014 1.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3840 -0.6293 0.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6800 0.1577 -0.9417 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7532 0.8870 1.9381 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2616 -1.4180 2.4063 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9799 -1.7394 -2.1559 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1758 -1.9084 -2.3688 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0647 -2.6351 -2.6978 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1173 1.4919 -1.8010 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7207 -0.0827 -1.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2162 0.8980 3.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7617 2.7918 1.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2380 1.8893 1.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0887 2.2015 0.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9907 -0.7294 2.3256 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2737 0.5950 -0.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0307 -2.5837 1.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5503 -1.9937 -0.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4014 -2.5033 -0.3880 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8260 -2.0818 1.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4554 0.1289 1.8502 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7111 2.5068 1.6584 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0896 2.4445 -0.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8671 1.0600 1.5153 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6517 2.6611 0.5790 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1340 -0.7682 0.7937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5566 -2.5298 -1.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0431 -1.2781 -2.2183 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7255 -2.8849 -0.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1415 2.5529 -0.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4647 1.5726 0.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0119 1.5920 1.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6736 2.0375 -1.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7205 0.8282 -2.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3844 -0.5118 -3.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2617 1.2743 -3.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7811 -2.2894 -0.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0171 -1.8442 1.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4999 -0.2092 1.8298 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3844 -0.1965 0.3731 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4545 -1.7011 -0.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3587 0.1512 -1.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5149 1.2092 -0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7962 1.3257 2.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4402 0.9099 2.8230 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2042 1.6001 1.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3319 -1.4804 2.2026 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7276 -2.3835 2.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1352 -1.0031 3.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3110 -3.6068 -2.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2681 0.9083 -2.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0317 2.1243 -1.6943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.2971 -1.9628 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1346 -0.4987 -2.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0742 0.9356 -1.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6691 -0.7036 -1.3841 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 6 3 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 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 26 30 1 0 23 31 1 6 31 32 2 0 31 33 1 0 13 34 1 6 9 35 1 6 10 3 1 0 18 13 1 0 28 23 1 0 14 9 1 0 24 17 1 0 2 36 1 0 4 37 1 0 4 38 1 0 4 39 1 0 5 40 1 1 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 10 46 1 1 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 14 51 1 1 15 52 1 0 15 53 1 0 16 54 1 0 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 21 60 1 6 22 61 1 0 24 62 1 6 25 63 1 0 25 64 1 0 27 65 1 0 27 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 M END

Standard InCHIKey	MQUFAARYGOUYEV-UAWZMHPWSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1
SMILES	O=C[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)C[C@@H](O)[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	3.106 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.212 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.539 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.36	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.047	Fsp³:	0.867
MCE-18:	108.571 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.681	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.36	Promiscuous compounds:	0.035

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.499	MDCK Permeability:	-5.128
Pgp-inhibitor:	0.003	Pgp-substrate:	0.003
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):	0.001
20% Bioavailability (F20%):	0.499	30% Bioavailability (F30%):	0.019
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.927	MRP1:	0.684
Plasma Protein Binding (PPB):	93.729%	Volume Distribution (VD):	-0.317
Fu:	6.202% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.116	BCRP inhibitor:	0.264
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.042
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.154
HLM stability:	0.078 ? 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):

2.276

Half-life (T1/2):

1.271

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.732	Drug-induced Liver Injury (DILI):	0.69
AMES Toxicity:	0.722	Rat Oral Acute Toxicity:	0.714
Maximum Recommended Daily Dose:	0.544	Skin Sensitization:	0.998
Carcinogencity:	0.982	Eye Corrosion:	0.006
Eye Irritation:	0.33	Respiratory Toxicity:	0.92
Drug-induced Neurotoxicity:	0.063	Ototoxicity:	0.585
Hematotoxicity:	0.797	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.551	Hek293 Cytotoxicity:	0.309
BCF:	1.001 ? 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:	3.95 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.444 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.833 ? 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
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[16880670]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[17409564]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	roots	n.a.	n.a.	PMID[18194870]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[21070025]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10187	Protoblastenia incrustans	Species	Psoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10820	Galium spurium	Species	Rubiaceae	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
Inhibition	1

Activity Type	# Activity
Organism	1
Others	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
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	0.0	%	PMID[23662817]
NPT2	Others	Unspecified	n.a.	IC50	=	59700.0	nM	PMID[18194870]

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 NPC222047 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	22369
0.1-0.2	23290
0.2-0.3	3342
0.3-0.4	574
0.4-0.5	208
0.5-0.6	39
0.6-0.7	15
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8308	Intermediate Similarity	NPC228784
0.8308	Intermediate Similarity	NPC324341
0.8308	Intermediate Similarity	NPC601810
0.7761	Intermediate Similarity	NPC298554
0.6901	Remote Similarity	NPC201657
0.6892	Remote Similarity	NPC601365
0.6806	Remote Similarity	NPC471588
0.64	Remote Similarity	NPC6255
0.6338	Remote Similarity	NPC480946
0.6338	Remote Similarity	NPC130577
0.6338	Remote Similarity	NPC142415
0.6338	Remote Similarity	NPC102683
0.6267	Remote Similarity	NPC187933
0.625	Remote Similarity	NPC270768
0.625	Remote Similarity	NPC59263
0.625	Remote Similarity	NPC210106
0.6145	Remote Similarity	NPC31839
0.6081	Remote Similarity	NPC29765
0.6071	Remote Similarity	NPC242611
0.573	Remote Similarity	NPC76999
0.5676	Remote Similarity	NPC198664
0.56	Remote Similarity	NPC182797
0.56	Remote Similarity	NPC282616
0.56	Remote Similarity	NPC275809
0.56	Remote Similarity	NPC121798
0.56	Remote Similarity	NPC84319
0.56	Remote Similarity	NPC234346
0.56	Remote Similarity	NPC52021
0.56	Remote Similarity	NPC52169
0.56	Remote Similarity	NPC488562
0.56	Remote Similarity	NPC599947
0.5526	Remote Similarity	NPC231063
0.5526	Remote Similarity	NPC282395
0.5526	Remote Similarity	NPC110308
0.5426	Remote Similarity	NPC488516
0.5395	Remote Similarity	NPC64872
0.5395	Remote Similarity	NPC25906
0.5395	Remote Similarity	NPC606443
0.5368	Remote Similarity	NPC80843
0.5325	Remote Similarity	NPC130278
0.5325	Remote Similarity	NPC158141
0.5325	Remote Similarity	NPC481360
0.5319	Remote Similarity	NPC480424
0.5309	Remote Similarity	NPC474727
0.5256	Remote Similarity	NPC209868
0.5238	Remote Similarity	NPC603645
0.5181	Remote Similarity	NPC188833
0.5135	Remote Similarity	NPC604575
0.5128	Remote Similarity	NPC106112
0.5128	Remote Similarity	NPC261935
0.5125	Remote Similarity	NPC130520
0.5065	Remote Similarity	NPC187722
0.5063	Remote Similarity	NPC202728
0.5063	Remote Similarity	NPC158059
0.5063	Remote Similarity	NPC200752
0.5063	Remote Similarity	NPC120840
0.5063	Remote Similarity	NPC136697
0.505	Remote Similarity	NPC488515

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC222047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6435
0.1-0.2	2660
0.2-0.3	51
0.3-0.4	4
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