NPASS Compound

Natural Product: NPC81738

Natural Product ID	NPC81738
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FWRZDNFXFFWBGP-LHHMAMHXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23757184
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 69 72 0 0 0 0 0 0 0 0999 V2000 6.8199 -2.3974 -1.5639 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3910 -2.9020 -0.3263 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6976 -2.1528 0.6006 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3880 -0.8272 0.3345 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6984 -0.0574 1.2394 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3118 -0.6182 2.4268 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6209 -1.9467 2.6961 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3162 -2.7241 1.7847 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6004 -4.0592 2.1100 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3879 1.3325 0.9320 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0591 1.5064 0.2283 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8713 2.9819 -0.0284 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8640 3.1608 -1.1174 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5244 2.6059 -0.8326 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4218 3.3755 -0.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6534 2.8358 0.0438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9939 1.5281 -0.3278 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0527 0.7679 -0.9570 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2022 1.3291 -1.1996 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3072 -0.5446 -1.3616 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2936 -1.2702 -2.0036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2274 1.1216 -0.0347 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9251 -0.0391 -0.2159 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5482 -0.4790 1.0992 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9273 -1.0117 0.9850 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2503 -1.6369 -0.3418 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4790 -1.0321 -1.4832 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3616 -0.8119 -2.6961 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -2.0380 -3.1936 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0498 0.2236 -1.0587 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0652 -3.0157 -0.3550 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8883 -0.0125 1.2596 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6577 -1.3847 1.7159 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3653 3.4539 1.3169 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4753 2.4061 1.6717 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9613 1.2084 1.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5362 0.0748 1.4735 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3476 -1.4272 -1.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4489 -3.1447 -2.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9455 -2.1904 -2.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7204 -0.4411 -0.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7653 -0.0806 3.1923 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3057 -2.3686 3.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4575 -4.4370 1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4043 1.9035 1.8781 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1813 1.7745 0.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0132 0.9086 -0.7040 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8488 3.4697 -0.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2138 2.7593 -2.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7389 4.2594 -1.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1823 4.4143 0.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3977 3.4701 0.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9023 0.6766 -1.7088 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5677 -2.3263 -2.1674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0827 -0.7682 -2.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5798 -1.2911 -1.3013 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3604 -0.8533 -0.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5761 0.4115 1.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0765 -1.7868 1.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3395 -1.4626 -0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6243 -1.6624 -1.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1646 -0.0898 -2.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7343 -0.3904 -3.5163 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8293 -2.0410 -2.9718 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9186 -3.5028 -0.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5524 0.8821 1.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -1.5785 1.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2251 3.5157 2.0062 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8827 4.4467 1.2635 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 5 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 17 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 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 12 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 8 3 1 0 36 11 1 0 19 14 1 0 30 23 1 0 1 38 1 0 1 39 1 0 1 40 1 0 4 41 1 0 6 42 1 0 7 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 11 47 1 6 12 48 1 6 13 49 1 0 13 50 1 0 15 51 1 0 16 52 1 0 19 53 1 0 21 54 1 0 21 55 1 0 21 56 1 0 23 57 1 6 24 58 1 1 25 59 1 1 26 60 1 6 27 61 1 6 28 62 1 0 28 63 1 0 29 64 1 0 31 65 1 0 32 66 1 0 33 67 1 0 34 68 1 0 34 69 1 0 M END

Standard InCHIKey	FWRZDNFXFFWBGP-LHHMAMHXSA-N
Standard InCHI	InChI=1S/C26H32O11/c1-33-19-9-14(3-5-17(19)28)8-16-15(12-35-25(16)32)7-13-4-6-18(20(10-13)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,21-24,26-31H,7-8,11-12H2,1-2H3/t15-,16+,21+,22+,23-,24+,26+/m0/s1
SMILES	COc1cc(ccc1O)C[C@@H]1[C@@H](Cc2ccc(c(c2)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)COC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	520.19	Volume:	502.264 ? Van der Waals volume.
Dense:	1.036	LogP:	0.086 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.706 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.355 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	24.0
TPSA:	164.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.286	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.166	Fsp³:	0.5
MCE-18:	88.667 ? 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:	0.592	Fluc inhibitor:	0.052 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.042 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.354 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.085	Promiscuous compounds:	0.193

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.93	MDCK Permeability:	-5.007
Pgp-inhibitor:	0.002	Pgp-substrate:	0.263
PAMPA:	0.545 ? 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):	0.376
20% Bioavailability (F20%):	0.789	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.261
Plasma Protein Binding (PPB):	78.054%	Volume Distribution (VD):	-0.347
Fu:	19.97% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.022
BSEP inhibitor:	0.248

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.971	CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.196 ? 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):

2.641

Half-life (T1/2):

4.097

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.185
Human Hepatotoxicity (H-HT):	0.972	Drug-induced Liver Injury (DILI):	0.993
AMES Toxicity:	0.966	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.071	Skin Sensitization:	0.998
Carcinogencity:	0.405	Eye Corrosion:	0.0
Eye Irritation:	0.156	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.088	Ototoxicity:	0.976
Hematotoxicity:	0.661	Drug-induced Nephrotoxicity:	0.972
Genotoxicity:	0.992	RPMI-8226 Immunitoxicity:	0.275
A549 Cytotoxicity:	0.543	Hek293 Cytotoxicity:	0.469
BCF:	0.723 ? 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:	3.419 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.984 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.214 ? 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
NPO12713	Brachylaena ramiflora	Species	Asteraceae	Eukaryota	twigs	Madagascar rainforest	n.a.	PMID[12193040]
NPO13045	Kielmeyera albopunctata	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762797]
NPO3935	Asplenium septentrionale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26016	Spheciospongia vagabunda	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12713	Brachylaena ramiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26016	Spheciospongia vagabunda	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6858	Achillea tuzsonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25196	Nuxia oppositifolia	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10799	Espeletia moritziana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11869	Vernonia leopoldi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13045	Kielmeyera albopunctata	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3935	Asplenium septentrionale	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5136	Colliguaja salicifolia	Species	Euphorbiaceae	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 NPC81738 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	12974
0.1-0.2	31309
0.2-0.3	4318
0.3-0.4	982
0.4-0.5	204
0.5-0.6	39
0.6-0.7	20
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299706
1.0	High Similarity	NPC115466
1.0	High Similarity	NPC61604
0.863	High Similarity	NPC245615
0.8551	High Similarity	NPC158635
0.8551	High Similarity	NPC229882
0.7821	Intermediate Similarity	NPC486549
0.7821	Intermediate Similarity	NPC486548
0.7722	Intermediate Similarity	NPC486546
0.725	Intermediate Similarity	NPC163635
0.6957	Remote Similarity	NPC300776
0.6957	Remote Similarity	NPC176814
0.6957	Remote Similarity	NPC4982
0.6957	Remote Similarity	NPC606629
0.6951	Remote Similarity	NPC486547
0.6829	Remote Similarity	NPC185307
0.6829	Remote Similarity	NPC470950
0.6353	Remote Similarity	NPC283995
0.6351	Remote Similarity	NPC278961
0.6351	Remote Similarity	NPC113680
0.6324	Remote Similarity	NPC68779
0.6324	Remote Similarity	NPC108598
0.6267	Remote Similarity	NPC282291
0.6267	Remote Similarity	NPC166137
0.625	Remote Similarity	NPC106920
0.625	Remote Similarity	NPC15811
0.619	Remote Similarity	NPC486545
0.619	Remote Similarity	NPC39657
0.6154	Remote Similarity	NPC478703
0.6154	Remote Similarity	NPC478704
0.5977	Remote Similarity	NPC129417
0.5977	Remote Similarity	NPC470235
0.5976	Remote Similarity	NPC471063
0.5972	Remote Similarity	NPC273657
0.5854	Remote Similarity	NPC38041
0.5854	Remote Similarity	NPC22150
0.5769	Remote Similarity	NPC216223
0.5753	Remote Similarity	NPC472024
0.5753	Remote Similarity	NPC270849
0.5682	Remote Similarity	NPC46092
0.5682	Remote Similarity	NPC478055
0.5676	Remote Similarity	NPC26653
0.5676	Remote Similarity	NPC80600
0.56	Remote Similarity	NPC5310
0.5529	Remote Similarity	NPC38699
0.5476	Remote Similarity	NPC18979
0.5467	Remote Similarity	NPC210015
0.5362	Remote Similarity	NPC223807
0.5294	Remote Similarity	NPC227902
0.5294	Remote Similarity	NPC279298
0.5294	Remote Similarity	NPC147596
0.5275	Remote Similarity	NPC112861
0.527	Remote Similarity	NPC9912
0.519	Remote Similarity	NPC145569
0.5176	Remote Similarity	NPC61594
0.5176	Remote Similarity	NPC286235
0.5135	Remote Similarity	NPC166040
0.5128	Remote Similarity	NPC100675
0.5128	Remote Similarity	NPC601691
0.5125	Remote Similarity	NPC276753
0.5125	Remote Similarity	NPC205796
0.5125	Remote Similarity	NPC469661
0.5116	Remote Similarity	NPC56735
0.5068	Remote Similarity	NPC211386
0.5063	Remote Similarity	NPC302378
0.5062	Remote Similarity	NPC246947
0.5062	Remote Similarity	NPC604095
0.506	Remote Similarity	NPC478705
0.5056	Remote Similarity	NPC44452

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC81738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3964
0.1-0.2	4980
0.2-0.3	191
0.3-0.4	15
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