NPASS Compound

Natural Product: NPC197443

Natural Product ID	NPC197443
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DMSHFFHLWVNSCH-KQHSUYLTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23583762
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 61 64 0 0 0 0 0 0 0 0999 V2000 -2.6863 -3.3797 -0.0299 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9298 -2.0495 -0.1457 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7103 -2.3480 -1.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3997 -1.6015 -0.3583 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4047 -2.4526 -0.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5062 -2.0032 0.6390 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5977 -0.6596 1.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6054 0.2393 0.7135 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5310 -0.2444 0.0307 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2940 0.9329 -0.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6698 1.1676 -0.0546 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1437 2.4089 -0.2870 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2621 3.4080 -0.6771 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1013 3.1358 -0.8324 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6046 1.8825 -0.6044 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9160 1.5132 -0.7558 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4329 1.0448 -2.0141 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7561 4.3095 -1.2298 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1813 5.3539 -1.1501 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4547 4.7455 -0.9754 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8075 0.3006 0.2527 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7988 -0.9524 -0.6232 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5141 -0.5533 -2.0691 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8976 -0.0899 1.5632 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1185 0.3242 2.1422 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6000 1.5707 1.0633 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0599 2.0403 2.2920 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7158 -0.1861 1.7057 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8527 0.3181 1.0375 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -2.8684 0.9527 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4322 -4.2289 0.5804 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9444 -3.7849 -1.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5390 -3.2708 0.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9666 -4.0826 0.4598 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6127 -1.8199 0.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8619 -2.0791 -2.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4588 -3.4247 -0.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3398 -3.5073 -0.3247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1888 2.6289 -0.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9288 0.0957 -1.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1732 1.8508 -2.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6210 1.0046 -2.7419 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0041 5.9603 -0.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1869 6.0195 -2.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7350 0.8506 -0.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8550 -1.3163 -0.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2729 0.2224 -2.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4930 -0.1438 -2.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7073 -1.4417 -2.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2426 1.4090 2.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9146 -0.0867 1.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2841 -0.1514 3.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2831 1.2305 3.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0255 2.1320 2.1690 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5564 2.9807 2.6134 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0463 1.3878 1.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7253 0.2482 -0.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7470 -0.2686 1.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4795 -4.6233 0.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3055 -4.7787 1.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5153 -4.3193 -0.5299 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 4 5 2 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 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 14 18 1 0 18 19 1 0 19 20 1 0 11 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 8 26 1 0 26 27 1 0 7 28 1 0 28 29 1 0 6 30 1 0 30 31 1 0 22 2 1 0 9 4 1 0 15 10 1 0 20 13 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 1 3 36 1 0 3 37 1 0 5 38 1 0 12 39 1 0 17 40 1 0 17 41 1 0 17 42 1 0 19 43 1 0 19 44 1 0 21 45 1 6 22 46 1 6 23 47 1 0 23 48 1 0 23 49 1 0 25 50 1 0 25 51 1 0 25 52 1 0 27 53 1 0 27 54 1 0 27 55 1 0 29 56 1 0 29 57 1 0 29 58 1 0 31 59 1 0 31 60 1 0 31 61 1 0 M END

Standard InCHIKey	DMSHFFHLWVNSCH-KQHSUYLTSA-N
Standard InCHI	InChI=1S/C24H30O7/c1-12-8-14-9-16(25-3)21(27-5)23(28-6)18(14)19-15(20(26-4)13(12)2)10-17-22(24(19)29-7)31-11-30-17/h9-10,12-13,20H,8,11H2,1-7H3/t12-,13-,20+/m0/s1
SMILES	C[C@H]1Cc2cc(c(c(c2-c2c(cc3c(c2OC)OCO3)[C@@H]([C@H]1C)OC)OC)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	430.2	Volume:	435.147 ? Van der Waals volume.
Dense:	0.989	LogP:	2.916 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.971 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.449 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	64.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.685	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.797	Fsp³:	0.5
MCE-18:	81.944 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.252	Fluc inhibitor:	0.329 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.442 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.259 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.267	Promiscuous compounds:	0.518

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.913	MDCK Permeability:	-4.741
Pgp-inhibitor:	0.673	Pgp-substrate:	0.037
PAMPA:	0.052 ? 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%):	0.01	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.3

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.769	MRP1:	0.979
Plasma Protein Binding (PPB):	89.146%	Volume Distribution (VD):	0.019
Fu:	8.803% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.907
OATP1B3 inhibitor:	0.956	BCRP inhibitor:	0.021
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.667
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.981	CYP2C9-substrate:	0.845
CYP2D6-inhibitor:	0.965	CYP2D6-substrate:	0.997
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.989
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.021
HLM stability:	0.629 ? 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):

5.411

Half-life (T1/2):

0.707

ADMET: Toxicity

hERG Blockers:	0.151	hERG Blockers (10um):	0.486
Human Hepatotoxicity (H-HT):	0.58	Drug-induced Liver Injury (DILI):	0.722
AMES Toxicity:	0.571	Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.387	Skin Sensitization:	0.527
Carcinogencity:	0.86	Eye Corrosion:	0.012
Eye Irritation:	0.682	Respiratory Toxicity:	0.818
Drug-induced Neurotoxicity:	0.624	Ototoxicity:	0.517
Hematotoxicity:	0.74	Drug-induced Nephrotoxicity:	0.566
Genotoxicity:	0.031	RPMI-8226 Immunitoxicity:	0.215
A549 Cytotoxicity:	0.461	Hek293 Cytotoxicity:	0.447
BCF:	2.538 ? 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:	4.371 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.83 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.228 ? 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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	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 NPC197443 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	28111
0.1-0.2	20071
0.2-0.3	1345
0.3-0.4	197
0.4-0.5	50
0.5-0.6	55
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC76415
0.8462	Intermediate Similarity	NPC218510
0.766	Intermediate Similarity	NPC145722
0.766	Intermediate Similarity	NPC256776
0.766	Intermediate Similarity	NPC185680
0.7368	Intermediate Similarity	NPC85141
0.7255	Intermediate Similarity	NPC141493
0.7234	Intermediate Similarity	NPC32189
0.7143	Intermediate Similarity	NPC216434
0.7143	Intermediate Similarity	NPC103448
0.7143	Intermediate Similarity	NPC606558
0.7119	Intermediate Similarity	NPC154971
0.7119	Intermediate Similarity	NPC121661
0.7115	Intermediate Similarity	NPC865
0.7069	Intermediate Similarity	NPC73467
0.7	Intermediate Similarity	NPC191352
0.6981	Remote Similarity	NPC184928
0.6949	Remote Similarity	NPC252286
0.6769	Remote Similarity	NPC63061
0.6769	Remote Similarity	NPC475229
0.6735	Remote Similarity	NPC474295
0.6452	Remote Similarity	NPC471154
0.6415	Remote Similarity	NPC326144
0.6316	Remote Similarity	NPC220577
0.6207	Remote Similarity	NPC230538
0.6207	Remote Similarity	NPC229172
0.6207	Remote Similarity	NPC103637
0.6207	Remote Similarity	NPC36531
0.597	Remote Similarity	NPC475756
0.5965	Remote Similarity	NPC327651
0.5965	Remote Similarity	NPC53722
0.5965	Remote Similarity	NPC201404
0.5965	Remote Similarity	NPC290714
0.5957	Remote Similarity	NPC283114
0.5957	Remote Similarity	NPC207702
0.5957	Remote Similarity	NPC149008
0.5932	Remote Similarity	NPC304821
0.5862	Remote Similarity	NPC172171
0.5862	Remote Similarity	NPC239254
0.5862	Remote Similarity	NPC318286
0.5797	Remote Similarity	NPC474606
0.5714	Remote Similarity	NPC471183
0.5714	Remote Similarity	NPC475856
0.5672	Remote Similarity	NPC126405
0.5672	Remote Similarity	NPC53669
0.5672	Remote Similarity	NPC77237
0.5672	Remote Similarity	NPC297271
0.5672	Remote Similarity	NPC224472
0.5672	Remote Similarity	NPC16791
0.5672	Remote Similarity	NPC217708
0.5667	Remote Similarity	NPC321958
0.5667	Remote Similarity	NPC327352
0.5667	Remote Similarity	NPC198129
0.5667	Remote Similarity	NPC252281
0.5667	Remote Similarity	NPC321696
0.5652	Remote Similarity	NPC476065
0.5593	Remote Similarity	NPC133934
0.5577	Remote Similarity	NPC87295
0.5556	Remote Similarity	NPC238834
0.5541	Remote Similarity	NPC215400
0.5507	Remote Similarity	NPC280778
0.5484	Remote Similarity	NPC322426
0.5484	Remote Similarity	NPC325122
0.5479	Remote Similarity	NPC311912
0.5429	Remote Similarity	NPC83049
0.5429	Remote Similarity	NPC320471
0.5429	Remote Similarity	NPC118162
0.5373	Remote Similarity	NPC198461
0.5333	Remote Similarity	NPC184684
0.5333	Remote Similarity	NPC184641
0.5312	Remote Similarity	NPC316989
0.5312	Remote Similarity	NPC325720
0.5312	Remote Similarity	NPC316676
0.5294	Remote Similarity	NPC473323
0.5278	Remote Similarity	NPC29727
0.5263	Remote Similarity	NPC133025
0.5231	Remote Similarity	NPC166506
0.5231	Remote Similarity	NPC110763
0.5217	Remote Similarity	NPC473425
0.5217	Remote Similarity	NPC258322
0.5152	Remote Similarity	NPC319749
0.5143	Remote Similarity	NPC79322
0.5065	Remote Similarity	NPC230531

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC197443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5714
0.1-0.2	3368
0.2-0.3	65
0.3-0.4	3
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