NPASS Compound

Natural Product: NPC39657

Natural Product ID	NPC39657
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Armandiside
IUPAC Name	(2S,3R,4S,5S,6R)-2-[4-[[(3S,4S,5R)-5-(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms	Armandiside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1911057
PubChem CID	57390294
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 78 0 0 0 0 0 0 0 0999 V2000 -3.6210 0.2916 1.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5806 -0.2867 -0.0002 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3956 -0.8533 -0.4535 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2771 -0.8478 0.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0576 -1.3823 0.0061 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0137 -1.9434 -1.2416 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0780 -1.9665 -2.0784 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3249 -1.4203 -1.7126 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3643 -1.4865 -2.6043 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6528 -1.0098 -2.5497 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1436 -0.3962 -3.8660 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5580 0.0297 -3.6559 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2382 -0.4899 -2.4458 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7117 -1.7547 -1.8594 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7048 -2.8917 -1.9446 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9505 -3.2724 -3.2696 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4952 -2.1434 -2.4048 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3413 0.5057 -1.4479 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3458 -0.1665 -4.8181 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3314 0.6561 -4.2617 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0608 -1.3305 0.9690 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8809 -0.0914 0.8752 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5204 0.0357 -0.4866 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7093 0.7265 -0.2197 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2292 0.1794 0.9149 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0991 1.1334 1.6495 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3530 0.7727 2.0479 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1898 1.6288 2.7427 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7160 2.9099 3.0406 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4587 3.2765 2.6421 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6300 2.4001 1.9423 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0460 4.5751 2.9713 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7609 4.9853 2.5777 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5546 3.7869 3.7399 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4670 1.3287 3.1706 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1599 0.1367 2.9840 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0608 -0.1792 1.7866 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2238 -1.5733 2.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3649 -1.4808 3.2152 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7944 1.0084 1.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4807 -0.5067 2.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5841 0.8383 1.4518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3644 -0.4111 1.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9731 -2.3685 -1.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0086 -2.4107 -3.0473 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8648 -0.2831 -1.7672 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1356 -1.2315 -4.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5327 1.1579 -3.5567 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3196 -0.6935 -2.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5187 -1.5913 -0.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2614 -3.7596 -1.3713 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6622 -2.6971 -1.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9025 -3.0926 -3.5141 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0519 0.0980 -0.5783 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9849 -0.8841 -4.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2781 0.7829 -5.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6312 -1.4480 2.0080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6855 -2.2391 0.8090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2595 0.8270 1.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8758 0.6460 -1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7862 -0.9409 -0.9041 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8449 -0.7300 0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7077 -0.2148 1.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6485 2.6777 1.6324 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0638 4.5424 3.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4785 4.6815 1.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7560 6.0975 2.6044 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6029 4.7471 3.3627 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1307 0.2395 2.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3322 -0.3158 4.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5026 -0.5918 2.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0123 0.5796 2.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3923 -1.8585 3.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5194 -2.2455 1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2151 -0.8018 3.9213 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 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 14 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 5 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 29 34 1 0 28 35 1 0 35 36 1 0 25 37 1 0 37 38 1 0 38 39 1 0 8 3 1 0 17 10 1 0 37 22 1 0 31 26 1 0 1 40 1 0 1 41 1 0 1 42 1 0 4 43 1 0 6 44 1 0 7 45 1 0 10 46 1 1 11 47 1 6 12 48 1 1 13 49 1 6 14 50 1 1 15 51 1 0 15 52 1 0 16 53 1 0 18 54 1 0 19 55 1 0 20 56 1 0 21 57 1 0 21 58 1 0 22 59 1 1 23 60 1 0 23 61 1 0 25 62 1 6 27 63 1 0 31 64 1 0 33 65 1 0 33 66 1 0 33 67 1 0 34 68 1 0 36 69 1 0 36 70 1 0 36 71 1 0 37 72 1 1 38 73 1 0 38 74 1 0 39 75 1 0 M END

Standard InCHIKey	SXFAXLRMEJZJPU-UQGLNZQASA-N
Standard InCHI	InChI=1S/C27H36O12/c1-34-18-7-13(4-5-17(18)38-27-25(33)24(32)23(31)21(11-29)39-27)6-15-12-37-26(16(15)10-28)14-8-19(35-2)22(30)20(9-14)36-3/h4-5,7-9,15-16,21,23-33H,6,10-12H2,1-3H3/t15-,16-,21-,23-,24+,25-,26+,27-/m1/s1
SMILES	COc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C[C@@H]1CO[C@@H](c2cc(c(c(c2)OC)O)OC)[C@@H]1CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.22	Volume:	530.986 ? Van der Waals volume.
Dense:	1.04	LogP:	-0.193 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.464 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.235 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	23.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.235	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.391	Fsp³:	0.556
MCE-18:	92.571 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.509	Fluc inhibitor:	0.104 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.05 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.314 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.083	Promiscuous compounds:	0.059

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.999	MDCK Permeability:	-5.274
Pgp-inhibitor:	0.034	Pgp-substrate:	0.315
PAMPA:	0.042 ? 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):	0.273
20% Bioavailability (F20%):	0.098	30% Bioavailability (F30%):	0.791
50% Bioavailability (F50%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036	MRP1:	0.321
Plasma Protein Binding (PPB):	76.809%	Volume Distribution (VD):	-0.282
Fu:	21.82% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.246
BSEP inhibitor:	0.207

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.67	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.026
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.983
HLM stability:	0.007 ? 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):

2.877

Half-life (T1/2):

4.254

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.066
Human Hepatotoxicity (H-HT):	0.866	Drug-induced Liver Injury (DILI):	0.952
AMES Toxicity:	0.928	Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.026	Skin Sensitization:	0.998
Carcinogencity:	0.203	Eye Corrosion:	0.0
Eye Irritation:	0.124	Respiratory Toxicity:	0.018
Drug-induced Neurotoxicity:	0.046	Ototoxicity:	0.972
Hematotoxicity:	0.666	Drug-induced Nephrotoxicity:	0.773
Genotoxicity:	0.708	RPMI-8226 Immunitoxicity:	0.211
A549 Cytotoxicity:	0.675	Hek293 Cytotoxicity:	0.369
BCF:	0.663 ? 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:	3.269 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.72 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.855 ? 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
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16259	Syringa reticulata	Species	Oleaceae	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	2

Activity Type	# Activity
Others	1
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	10640.0	nM	PMID[21955940]
NPT1	Others	Radical scavenging activity	n.a.	EC50	>	100000.0	nM	PMID[10691710]

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 NPC39657 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	14755
0.1-0.2	30409
0.2-0.3	3746
0.3-0.4	737
0.4-0.5	146
0.5-0.6	41
0.6-0.7	18
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8649	High Similarity	NPC470950
0.8451	Intermediate Similarity	NPC471063
0.8219	Intermediate Similarity	NPC605526
0.7922	Intermediate Similarity	NPC185307
0.72	Intermediate Similarity	NPC286235
0.6353	Remote Similarity	NPC283995
0.625	Remote Similarity	NPC38041
0.625	Remote Similarity	NPC22150
0.6234	Remote Similarity	NPC216129
0.6234	Remote Similarity	NPC130449
0.6234	Remote Similarity	NPC248132
0.6203	Remote Similarity	NPC158635
0.6203	Remote Similarity	NPC229882
0.619	Remote Similarity	NPC299706
0.619	Remote Similarity	NPC245615
0.619	Remote Similarity	NPC115466
0.619	Remote Similarity	NPC61604
0.6163	Remote Similarity	NPC129417
0.6133	Remote Similarity	NPC276753
0.6133	Remote Similarity	NPC205796
0.6076	Remote Similarity	NPC606627
0.6053	Remote Similarity	NPC246947
0.6049	Remote Similarity	NPC279298
0.5946	Remote Similarity	NPC486558
0.5862	Remote Similarity	NPC163635
0.5753	Remote Similarity	NPC472024
0.5753	Remote Similarity	NPC270849
0.5694	Remote Similarity	NPC206882
0.5682	Remote Similarity	NPC46092
0.5682	Remote Similarity	NPC478055
0.5676	Remote Similarity	NPC26653
0.5676	Remote Similarity	NPC80600
0.5618	Remote Similarity	NPC486548
0.5618	Remote Similarity	NPC470235
0.5542	Remote Similarity	NPC51328
0.5542	Remote Similarity	NPC55158
0.5526	Remote Similarity	NPC282833
0.5513	Remote Similarity	NPC64201
0.5476	Remote Similarity	NPC18979
0.5444	Remote Similarity	NPC112861
0.534	Remote Similarity	NPC475224
0.5325	Remote Similarity	NPC95392
0.5325	Remote Similarity	NPC84013
0.5325	Remote Similarity	NPC55715
0.5325	Remote Similarity	NPC35877
0.5275	Remote Similarity	NPC486549
0.527	Remote Similarity	NPC9912
0.5263	Remote Similarity	NPC187998
0.5263	Remote Similarity	NPC257582
0.5263	Remote Similarity	NPC241522
0.5217	Remote Similarity	NPC486546
0.5195	Remote Similarity	NPC248355
0.5185	Remote Similarity	NPC118385
0.5135	Remote Similarity	NPC166040
0.5125	Remote Similarity	NPC278961
0.5125	Remote Similarity	NPC5262
0.5125	Remote Similarity	NPC113680
0.5119	Remote Similarity	NPC472713
0.5116	Remote Similarity	NPC227902
0.5111	Remote Similarity	NPC186316
0.5109	Remote Similarity	NPC476356
0.5063	Remote Similarity	NPC302378
0.5062	Remote Similarity	NPC37468
0.5062	Remote Similarity	NPC604095

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC39657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3802
0.1-0.2	5197
0.2-0.3	141
0.3-0.4	10
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