NPASS Compound

Natural Product: NPC63061

Natural Product ID	NPC63061
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Arisanschinin M
IUPAC Name	n.a.
Synonyms	Arisanschinin M
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2313593
PubChem CID	71521607
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 71 75 0 0 0 0 0 0 0 0999 V2000 4.9076 1.6195 1.3874 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7471 2.3111 0.9769 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8440 1.6304 0.1699 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9509 1.6668 -1.1944 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9469 2.3711 -1.8043 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0491 2.4030 -3.2032 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0258 0.9713 -1.9972 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0913 0.3121 -1.3651 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9590 0.2567 0.0437 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8244 0.9091 0.8161 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7360 0.8862 2.1817 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3700 -0.0694 2.9958 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0247 -0.5289 0.8371 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1397 -1.9220 0.9801 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9054 -2.8734 0.0253 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 -2.7809 -1.3001 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5356 -1.7912 -2.2865 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0752 -0.3772 -2.2772 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1403 -0.2243 -1.3811 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2433 1.0716 -0.8419 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3664 1.9105 -1.2752 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1615 1.6370 0.1439 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3200 1.4365 1.4129 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0106 0.0556 1.5351 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8049 -0.6854 2.3817 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6338 -2.0671 2.5395 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6166 -2.6609 1.7895 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5490 -2.5323 3.4360 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1587 -1.4413 4.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8778 -0.3772 3.2405 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1999 3.1315 0.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4816 1.0386 0.3122 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3525 1.7759 1.3290 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5624 3.0997 0.9098 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2368 1.1406 -1.0217 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0538 -1.8368 -2.5581 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1780 -4.1982 -1.8852 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8216 1.4097 2.4621 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0303 0.6425 0.8455 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8036 2.2781 1.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8640 3.0865 -3.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2396 1.3727 -3.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0977 2.7992 -3.5978 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 0.9863 -3.0850 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9431 -0.7449 2.3478 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5848 -0.6191 3.5534 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0461 0.4000 3.7492 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9431 -2.6394 -0.0334 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7259 -3.8651 0.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9374 -2.6048 -1.0208 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1351 -2.1920 -3.3038 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0896 0.1303 -3.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4634 -3.7561 1.8884 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6832 -1.2381 5.0822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2278 -1.6385 4.1840 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2884 3.6208 1.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9127 3.5137 -0.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1798 3.4470 -0.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4887 -0.0282 0.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3255 1.2668 1.3575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8779 1.8555 2.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2382 3.1597 0.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3340 1.1138 -0.8629 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8861 1.9818 -1.6213 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9899 0.1908 -1.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2135 -1.3380 -3.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -2.9166 -2.7195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6462 -1.3689 -1.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0712 -4.1772 -2.9490 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2417 -4.5369 -1.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4773 -4.8595 -1.3073 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 1 0 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 9 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 1 0 22 31 1 6 22 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 17 36 1 0 16 37 1 0 10 3 1 0 24 13 1 0 30 25 1 0 18 8 1 0 27 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 6 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 12 45 1 0 12 46 1 0 12 47 1 0 15 48 1 0 15 49 1 0 16 50 1 1 17 51 1 6 18 52 1 6 27 53 1 0 29 54 1 0 29 55 1 0 31 56 1 0 31 57 1 0 31 58 1 0 32 59 1 1 33 60 1 0 33 61 1 0 34 62 1 0 35 63 1 0 35 64 1 0 35 65 1 0 36 66 1 0 36 67 1 0 36 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 M END

Standard InCHIKey	GHEBHJULQBRZNT-RKZUNUFISA-N
Standard InCHI	InChI=1S/C28H34O9/c1-13-8-16-9-19-24(35-12-34-19)26-20(16)21-17(10-18(31-5)23(32-6)25(21)33-7)22(15(13)3)36-27(30)28(4,37-26)14(2)11-29/h9-10,13-15,22,29H,8,11-12H2,1-7H3/t13-,14+,15-,22+,28+/m0/s1
SMILES	COc1c(OC)cc2c(c1OC)c1c3C[C@@H]([C@@H]([C@H]2OC(=O)[C@@](Oc1c1c(c3)OCO1)(C)[C@@H](CO)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	514.22	Volume:	510.719 ? Van der Waals volume.
Dense:	1.007	LogP:	3.584 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.147 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.042 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	28.0
TPSA:	101.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.585	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.737	Fsp³:	0.536
MCE-18:	108.209 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.661	Fluc inhibitor:	0.24 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.655 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.393 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.049	Promiscuous compounds:	0.552

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.043	MDCK Permeability:	-4.808
Pgp-inhibitor:	0.342	Pgp-substrate:	0.033
PAMPA:	0.28 ? 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%):	0.157	30% Bioavailability (F30%):	0.031
50% Bioavailability (F50%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.623	MRP1:	0.995
Plasma Protein Binding (PPB):	94.734%	Volume Distribution (VD):	0.018
Fu:	5.157% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.947
OATP1B3 inhibitor:	0.872	BCRP inhibitor:	0.069
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.324
CYP2C9-inhibitor:	0.989	CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.034	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.979	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.025
HLM stability:	0.592 ? 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):

5.65

Half-life (T1/2):

0.834

ADMET: Toxicity

hERG Blockers:	0.06	hERG Blockers (10um):	0.301
Human Hepatotoxicity (H-HT):	0.83	Drug-induced Liver Injury (DILI):	0.927
AMES Toxicity:	0.887	Rat Oral Acute Toxicity:	0.525
Maximum Recommended Daily Dose:	0.647	Skin Sensitization:	0.99
Carcinogencity:	0.98	Eye Corrosion:	0.0
Eye Irritation:	0.204	Respiratory Toxicity:	0.583
Drug-induced Neurotoxicity:	0.671	Ototoxicity:	0.64
Hematotoxicity:	0.874	Drug-induced Nephrotoxicity:	0.94
Genotoxicity:	0.476	RPMI-8226 Immunitoxicity:	0.378
A549 Cytotoxicity:	0.849	Hek293 Cytotoxicity:	0.646
BCF:	1.763 ? 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:	4.046 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.261 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.118 ? 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
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	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
Inhibition	1

Activity Type	# Activity
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
NPT2	Others	Unspecified	n.a.	Inhibition	=	4.87	%	Open TG-GATES in vivo data: Organ Weight

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 NPC63061 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	15291
0.1-0.2	32646
0.2-0.3	1693
0.3-0.4	125
0.4-0.5	43
0.5-0.6	49
0.6-0.7	4
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	Natural Product ID
0.7385	Intermediate Similarity	NPC76415
0.7385	Intermediate Similarity	NPC218510
0.6571	Remote Similarity	NPC85141
0.6308	Remote Similarity	NPC865
0.6154	Remote Similarity	NPC475229
0.6081	Remote Similarity	NPC471154
0.5897	Remote Similarity	NPC475756
0.5758	Remote Similarity	NPC326144
0.575	Remote Similarity	NPC474606
0.5658	Remote Similarity	NPC191352
0.5625	Remote Similarity	NPC145722
0.5625	Remote Similarity	NPC476065
0.5625	Remote Similarity	NPC256776
0.5625	Remote Similarity	NPC185680
0.5542	Remote Similarity	NPC238834
0.5526	Remote Similarity	NPC154971
0.5526	Remote Similarity	NPC121661
0.5467	Remote Similarity	NPC73467
0.5443	Remote Similarity	NPC126405
0.5443	Remote Similarity	NPC53669
0.5443	Remote Similarity	NPC77237
0.5443	Remote Similarity	NPC297271
0.5443	Remote Similarity	NPC224472
0.5443	Remote Similarity	NPC16791
0.5443	Remote Similarity	NPC217708
0.5441	Remote Similarity	NPC141493
0.5429	Remote Similarity	NPC327651
0.5395	Remote Similarity	NPC252286
0.5352	Remote Similarity	NPC318286
0.5349	Remote Similarity	NPC215400
0.5333	Remote Similarity	NPC325720
0.5333	Remote Similarity	NPC316676
0.5312	Remote Similarity	NPC32189
0.5303	Remote Similarity	NPC216434
0.5303	Remote Similarity	NPC103448
0.5303	Remote Similarity	NPC606558
0.5286	Remote Similarity	NPC184928
0.5278	Remote Similarity	NPC220577
0.5205	Remote Similarity	NPC321958
0.5205	Remote Similarity	NPC327352
0.5205	Remote Similarity	NPC198129
0.5205	Remote Similarity	NPC304821
0.5205	Remote Similarity	NPC230538
0.5205	Remote Similarity	NPC252281
0.5205	Remote Similarity	NPC321696
0.5205	Remote Similarity	NPC229172
0.5205	Remote Similarity	NPC103637
0.5205	Remote Similarity	NPC36531
0.519	Remote Similarity	NPC198461
0.5122	Remote Similarity	NPC280778
0.5119	Remote Similarity	NPC29727
0.5114	Remote Similarity	NPC230531
0.5067	Remote Similarity	NPC322426
0.5067	Remote Similarity	NPC325122
0.5067	Remote Similarity	NPC473989

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC63061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4594
0.1-0.2	4496
0.2-0.3	60
0.3-0.4	0
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