NPASS Compound

Natural Product: NPC77861

Natural Product ID	NPC77861
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-(7''r,8''r)-Saucerneol J
IUPAC Name	4-[(2S,3R,4R,5R)-5-[4-[(1R,2R)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3105543
PubChem CID	73890954
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

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 74 77 0 0 0 0 0 0 0 0999 V2000 -3.6065 -0.4150 -2.4275 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5081 0.8960 -1.6552 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0022 1.2167 -1.6110 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9140 2.7479 -1.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6011 0.6520 -0.3098 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3459 -0.0779 -0.2577 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6060 -0.1435 -1.2255 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7749 -0.8662 -1.0926 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0396 -1.5711 0.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0768 -1.5212 1.0645 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0800 -0.7974 0.9152 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3452 -2.2431 2.2394 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3769 -2.2052 3.2834 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1921 -2.2943 0.2043 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2555 -2.4848 -0.6362 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4829 -3.9407 -1.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5785 -1.9944 -0.0707 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5494 -0.5416 0.1916 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9063 -0.0939 1.3249 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8510 1.2629 1.6164 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4514 2.1792 0.7546 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0835 1.7081 -0.3637 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1524 0.3692 -0.6752 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6795 2.6183 -1.2192 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3539 2.1963 -2.4007 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4209 3.5453 1.0063 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9000 -2.6464 1.1137 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6904 -0.1131 0.1743 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7586 0.7060 -0.1941 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0671 0.1943 0.1708 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4215 -1.1250 -0.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6899 -1.5144 0.3567 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6059 -0.6375 0.9154 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2543 0.6829 1.1093 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9913 1.0613 0.7302 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1859 1.5498 1.6714 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7927 2.8974 1.8565 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8802 -1.0541 1.2893 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1841 -0.2996 -3.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6599 -0.7304 -2.5765 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9777 -1.1906 -1.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0834 1.6928 -2.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4943 0.8723 -2.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0815 3.1056 -2.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8474 3.2087 -1.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7100 3.1327 -0.5848 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5246 1.5049 0.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4462 0.3933 -2.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4976 -0.8861 -1.8893 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7922 -0.7964 1.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5305 -2.7629 3.0184 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8447 -2.6646 4.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1571 -1.1446 3.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1170 -1.9428 -1.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5781 -4.4288 -1.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3304 -3.9423 -1.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8157 -4.5243 -0.1229 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3809 -2.2078 -0.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4429 -0.8229 1.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3442 1.5914 2.5059 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6504 -0.0162 -1.5583 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8781 3.0958 -2.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0514 1.3659 -2.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5806 1.8071 -3.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1847 4.0280 1.4720 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0730 -2.8482 1.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5664 1.6899 0.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7354 -1.8495 -0.4562 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9503 -2.5627 0.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7474 2.1220 0.9004 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5816 3.4994 2.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8362 3.0003 2.3865 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6287 3.3277 0.8298 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1223 -2.0199 1.1851 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 3 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 9 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 17 27 1 0 5 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 29 2 1 0 35 30 1 0 11 6 1 0 23 18 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 6 3 43 1 6 4 44 1 0 4 45 1 0 4 46 1 0 5 47 1 1 7 48 1 0 8 49 1 0 11 50 1 0 13 51 1 0 13 52 1 0 13 53 1 0 15 54 1 6 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 6 19 59 1 0 20 60 1 0 23 61 1 0 25 62 1 0 25 63 1 0 25 64 1 0 26 65 1 0 27 66 1 0 29 67 1 1 31 68 1 0 32 69 1 0 35 70 1 0 37 71 1 0 37 72 1 0 37 73 1 0 38 74 1 0 M END

Standard InCHIKey	GIBPGXUIRFWSNY-ZCZCRYHXSA-N
Standard InCHI	InChI=1S/C30H36O8/c1-16-17(2)30(38-29(16)20-8-11-23(32)26(14-20)35-5)21-9-12-24(27(15-21)36-6)37-18(3)28(33)19-7-10-22(31)25(13-19)34-4/h7-18,28-33H,1-6H3/t16-,17-,18-,28+,29+,30-/m1/s1
SMILES	C[C@@H]1[C@@H](C)[C@H](c2ccc(c(c2)OC)O[C@H](C)[C@@H](c2ccc(c(c2)OC)O)O)O[C@@H]1c1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	524.24	Volume:	539.804 ? Van der Waals volume.
Dense:	0.971	LogP:	2.35 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.544 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.877 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	106.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.327	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.032	Fsp³:	0.4
MCE-18:	86.143 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.779	Fluc inhibitor:	0.432 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.044 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.153 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.257	Promiscuous compounds:	0.277

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.036	MDCK Permeability:	-4.761
Pgp-inhibitor:	0.058	Pgp-substrate:	0.161
PAMPA:	0.129 ? 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%):	0.033	30% Bioavailability (F30%):	0.037
50% Bioavailability (F50%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.981
Plasma Protein Binding (PPB):	90.542%	Volume Distribution (VD):	0.03
Fu:	9.432% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.181
BSEP inhibitor:	0.897

ADMET: Metabolism

CYP1A2-inhibitor:	0.99	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.703
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.013	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

9.329

Half-life (T1/2):

1.956

ADMET: Toxicity

hERG Blockers:	0.21	hERG Blockers (10um):	0.598
Human Hepatotoxicity (H-HT):	0.808	Drug-induced Liver Injury (DILI):	0.601
AMES Toxicity:	0.579	Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.503	Skin Sensitization:	0.299
Carcinogencity:	0.285	Eye Corrosion:	0.002
Eye Irritation:	0.59	Respiratory Toxicity:	0.769
Drug-induced Neurotoxicity:	0.356	Ototoxicity:	0.713
Hematotoxicity:	0.302	Drug-induced Nephrotoxicity:	0.706
Genotoxicity:	0.697	RPMI-8226 Immunitoxicity:	0.231
A549 Cytotoxicity:	0.631	Hek293 Cytotoxicity:	0.704
BCF:	0.897 ? 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:	3.454 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.763 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.11 ? 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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
EC50	1
Ratio CC50/EC50	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
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	6950.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	=	3.3	n.a.	PMID[21925888]

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 NPC77861 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	15493
0.1-0.2	29636
0.2-0.3	4078
0.3-0.4	472
0.4-0.5	120
0.5-0.6	22
0.6-0.7	17
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8254	Intermediate Similarity	NPC304048
0.7368	Intermediate Similarity	NPC260842
0.7368	Intermediate Similarity	NPC93783
0.7368	Intermediate Similarity	NPC320380
0.7302	Intermediate Similarity	NPC470372
0.7273	Intermediate Similarity	NPC11258
0.7273	Intermediate Similarity	NPC21867
0.7273	Intermediate Similarity	NPC45774
0.7273	Intermediate Similarity	NPC74914
0.6765	Remote Similarity	NPC226153
0.6667	Remote Similarity	NPC179521
0.6562	Remote Similarity	NPC302506
0.6562	Remote Similarity	NPC241846
0.6562	Remote Similarity	NPC93610
0.6452	Remote Similarity	NPC58607
0.6452	Remote Similarity	NPC191037
0.6452	Remote Similarity	NPC178284
0.6393	Remote Similarity	NPC142547
0.6393	Remote Similarity	NPC228469
0.6296	Remote Similarity	NPC282703
0.6296	Remote Similarity	NPC184733
0.6296	Remote Similarity	NPC128208
0.6296	Remote Similarity	NPC129570
0.6296	Remote Similarity	NPC63238
0.6296	Remote Similarity	NPC602603
0.6102	Remote Similarity	NPC487683
0.5972	Remote Similarity	NPC114119
0.5972	Remote Similarity	NPC471415
0.5902	Remote Similarity	NPC488986
0.5763	Remote Similarity	NPC158331
0.5667	Remote Similarity	NPC487684
0.5417	Remote Similarity	NPC470097
0.5397	Remote Similarity	NPC27843
0.5397	Remote Similarity	NPC7171
0.5352	Remote Similarity	NPC487682
0.5303	Remote Similarity	NPC203831
0.5273	Remote Similarity	NPC216929
0.5273	Remote Similarity	NPC312713
0.5273	Remote Similarity	NPC126935
0.5273	Remote Similarity	NPC65933
0.5273	Remote Similarity	NPC57268
0.5273	Remote Similarity	NPC172676
0.5254	Remote Similarity	NPC242807
0.5254	Remote Similarity	NPC153739
0.5152	Remote Similarity	NPC9370
0.5152	Remote Similarity	NPC287495
0.5072	Remote Similarity	NPC291101
0.5072	Remote Similarity	NPC266197

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC77861 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3796
0.1-0.2	5107
0.2-0.3	239
0.3-0.4	7
0.4-0.5	1
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