NPASS Compound

Natural Product: NPC4328

Natural Product ID	NPC4328
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Clematomandshurica Saponin C
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4S,5R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	Clematomandshurica Saponin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1171454
PubChem CID	11994185
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

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Standard InCHIKey	FICAKDVNAHFTMY-JYHFIEJESA-N
Standard InCHI	InChI=1S/C76H124O39/c1-27-40(81)46(87)52(93)64(103-27)111-58-33(22-78)106-62(55(96)49(58)90)101-25-35-44(85)48(89)54(95)67(109-35)115-70(99)76-18-16-71(3,4)20-30(76)29-10-11-38-73(7)14-13-39(72(5,6)37(73)12-15-75(38,9)74(29,8)17-19-76)110-69-61(42(83)31(80)24-100-69)114-68-57(98)60(41(82)28(2)104-68)113-63-51(92)45(86)36(26-102-63)108-65-56(97)50(91)59(34(23-79)107-65)112-66-53(94)47(88)43(84)32(21-77)105-66/h10,27-28,30-69,77-98H,11-26H2,1-9H3/t27-,28-,30-,31-,32+,33+,34+,35+,36+,37-,38+,39-,40-,41-,42-,43+,44+,45+,46+,47-,48-,49+,50+,51+,52+,53+,54+,55+,56+,57+,58+,59+,60+,61+,62+,63-,64-,65-,66-,67-,68-,69-,73-,74+,75+,76-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@@]34CCC(C[C@H]4C4=CC[C@H]5[C@@]([C@@]4(CC3)C)(C)CC[C@@H]3[C@]5(C)CC[C@@H](C3(C)C)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O[C@@H]3OC[C@H]([C@H]([C@H]3O)O)O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)O)O)O)(C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1660.77	Volume:	1549.363 ? Van der Waals volume.
Dense:	1.072	LogP:	-0.518 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.363 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.967 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	21.0	Rigid Bonds:	75.0
TPSA:	609.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	39.0
H-Bond Donor:	22.0	Rings:	13.0
Heavy Atoms:	39.0

MedChem Properties

QED Drug-Likeness Score:	0.031	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.388	Fsp³:	0.961
MCE-18:	283.342 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.714	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.464	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.733	MDCK Permeability:	-4.826
Pgp-inhibitor:	0.0	Pgp-substrate:	0.984
PAMPA:	1.0 ? 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):	1.0
20% Bioavailability (F20%):	0.956	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	46.845%	Volume Distribution (VD):	-0.203
Fu:	23.599% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.269
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):

-2.211

Half-life (T1/2):

6.104

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.817	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.905	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.306	RPMI-8226 Immunitoxicity:	0.66
A549 Cytotoxicity:	0.992	Hek293 Cytotoxicity:	0.354
BCF:	1.205 ? 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:	3.472 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.974 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.933 ? 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
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[15387651]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots and rhizomes	Shaoguan, Guangdong Province, China	2007-Dec	PMID[20540535]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6583	Clematis chinensis	Species	Ranunculaceae	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
IC50	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	>	50000.0	nM	PMID[12617583]
NPT30	Individual protein	Cyclooxygenase-1	Homo sapiens	IC50	>	50000.0	nM	PMID[22365754]

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 NPC4328 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	25881
0.1-0.2	20237
0.2-0.3	2448
0.3-0.4	668
0.4-0.5	370
0.5-0.6	81
0.6-0.7	55
0.7-0.8	0
0.8-0.85	12
0.85-0.9	8
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261506
0.9909	High Similarity	NPC305981
0.9727	High Similarity	NPC41061
0.9727	High Similarity	NPC227551
0.9381	High Similarity	NPC236638
0.9381	High Similarity	NPC294453
0.9298	High Similarity	NPC298034
0.9298	High Similarity	NPC71065
0.9182	High Similarity	NPC135904
0.9123	High Similarity	NPC43550
0.906	High Similarity	NPC250247
0.9	High Similarity	NPC79643
0.8909	High Similarity	NPC60557
0.8909	High Similarity	NPC67857
0.8772	High Similarity	NPC481080
0.8718	High Similarity	NPC202828
0.8718	High Similarity	NPC119592
0.8673	High Similarity	NPC123199
0.8571	High Similarity	NPC475287
0.85	High Similarity	NPC220160
0.8475	Intermediate Similarity	NPC65105
0.8305	Intermediate Similarity	NPC110633
0.825	Intermediate Similarity	NPC481081
0.8246	Intermediate Similarity	NPC76972
0.8246	Intermediate Similarity	NPC469782
0.8246	Intermediate Similarity	NPC204414
0.8142	Intermediate Similarity	NPC481078
0.812	Intermediate Similarity	NPC475160
0.812	Intermediate Similarity	NPC473714
0.8091	Intermediate Similarity	NPC63159
0.8067	Intermediate Similarity	NPC476068
0.8017	Intermediate Similarity	NPC293330
0.7951	Intermediate Similarity	NPC136768
0.7899	Intermediate Similarity	NPC488560
0.7895	Intermediate Similarity	NPC295823
0.7895	Intermediate Similarity	NPC174720
0.7895	Intermediate Similarity	NPC475467
0.7818	Intermediate Similarity	NPC112352
0.7797	Intermediate Similarity	NPC165204
0.7787	Intermediate Similarity	NPC258617
0.7786	Intermediate Similarity	NPC469778
0.7754	Intermediate Similarity	NPC469776
0.7714	Intermediate Similarity	NPC32723
0.766	Intermediate Similarity	NPC481323
0.7552	Intermediate Similarity	NPC135334
0.7534	Intermediate Similarity	NPC295941
0.7521	Intermediate Similarity	NPC100639
0.75	Intermediate Similarity	NPC481324
0.7339	Intermediate Similarity	NPC57484
0.7302	Intermediate Similarity	NPC161717
0.7295	Intermediate Similarity	NPC155410
0.7288	Intermediate Similarity	NPC241909
0.7254	Intermediate Similarity	NPC469775
0.7241	Intermediate Similarity	NPC475504
0.7222	Intermediate Similarity	NPC469774
0.7211	Intermediate Similarity	NPC469777
0.7155	Intermediate Similarity	NPC148417
0.7117	Intermediate Similarity	NPC48499
0.7077	Intermediate Similarity	NPC224381
0.7075	Intermediate Similarity	NPC100925
0.7067	Intermediate Similarity	NPC469772
0.7059	Intermediate Similarity	NPC481079
0.7	Intermediate Similarity	NPC70809
0.6992	Remote Similarity	NPC192600
0.6983	Remote Similarity	NPC104071
0.6974	Remote Similarity	NPC469773
0.6953	Remote Similarity	NPC475514
0.6923	Remote Similarity	NPC102439
0.6923	Remote Similarity	NPC46665
0.6746	Remote Similarity	NPC219180
0.6746	Remote Similarity	NPC251263
0.6693	Remote Similarity	NPC470218
0.6667	Remote Similarity	NPC469946
0.6618	Remote Similarity	NPC480422
0.6555	Remote Similarity	NPC160415
0.65	Remote Similarity	NPC480475
0.6471	Remote Similarity	NPC223301
0.6471	Remote Similarity	NPC171544
0.6441	Remote Similarity	NPC295371
0.6423	Remote Similarity	NPC104372
0.641	Remote Similarity	NPC475516
0.6393	Remote Similarity	NPC297263
0.6385	Remote Similarity	NPC54636
0.6364	Remote Similarity	NPC473459
0.6357	Remote Similarity	NPC475209
0.629	Remote Similarity	NPC114484
0.6279	Remote Similarity	NPC133818
0.6271	Remote Similarity	NPC235405
0.627	Remote Similarity	NPC31838
0.627	Remote Similarity	NPC187290
0.626	Remote Similarity	NPC222580
0.6241	Remote Similarity	NPC286457
0.624	Remote Similarity	NPC301449
0.624	Remote Similarity	NPC601290
0.623	Remote Similarity	NPC10607
0.623	Remote Similarity	NPC251768
0.6218	Remote Similarity	NPC249848
0.6218	Remote Similarity	NPC107966
0.619	Remote Similarity	NPC80986
0.6179	Remote Similarity	NPC475591
0.6179	Remote Similarity	NPC236870
0.6179	Remote Similarity	NPC235438
0.6154	Remote Similarity	NPC29069
0.6148	Remote Similarity	NPC30735
0.6115	Remote Similarity	NPC102505
0.6115	Remote Similarity	NPC488514
0.6111	Remote Similarity	NPC324875
0.6111	Remote Similarity	NPC292677
0.6098	Remote Similarity	NPC164389
0.6096	Remote Similarity	NPC472268
0.6066	Remote Similarity	NPC192791
0.6061	Remote Similarity	NPC471550
0.6061	Remote Similarity	NPC191827
0.6058	Remote Similarity	NPC302543
0.6045	Remote Similarity	NPC21691
0.6029	Remote Similarity	NPC471385
0.6027	Remote Similarity	NPC297950
0.6	Remote Similarity	NPC13998
0.5984	Remote Similarity	NPC161674
0.597	Remote Similarity	NPC85154
0.5968	Remote Similarity	NPC159309
0.5968	Remote Similarity	NPC86222
0.5956	Remote Similarity	NPC470876
0.595	Remote Similarity	NPC473373
0.595	Remote Similarity	NPC150400
0.5942	Remote Similarity	NPC309223
0.5938	Remote Similarity	NPC480473
0.5938	Remote Similarity	NPC480474
0.5932	Remote Similarity	NPC214484
0.5931	Remote Similarity	NPC489208
0.5902	Remote Similarity	NPC39211
0.5891	Remote Similarity	NPC104137
0.5891	Remote Similarity	NPC475486
0.5891	Remote Similarity	NPC26626
0.5887	Remote Similarity	NPC309714
0.5874	Remote Similarity	NPC33012
0.5865	Remote Similarity	NPC166422
0.584	Remote Similarity	NPC101744
0.584	Remote Similarity	NPC173859
0.584	Remote Similarity	NPC148603
0.5833	Remote Similarity	NPC123522
0.5806	Remote Similarity	NPC472269
0.5804	Remote Similarity	NPC8524
0.5798	Remote Similarity	NPC90856
0.5794	Remote Similarity	NPC68175
0.5789	Remote Similarity	NPC470911
0.5781	Remote Similarity	NPC281148
0.5766	Remote Similarity	NPC473452
0.5766	Remote Similarity	NPC480418
0.5753	Remote Similarity	NPC475368
0.5748	Remote Similarity	NPC609763
0.5746	Remote Similarity	NPC480419
0.5735	Remote Similarity	NPC4749
0.5726	Remote Similarity	NPC263756
0.5726	Remote Similarity	NPC213674
0.5725	Remote Similarity	NPC75287
0.5704	Remote Similarity	NPC283417
0.5704	Remote Similarity	NPC200049
0.5672	Remote Similarity	NPC471384
0.5664	Remote Similarity	NPC480417
0.5659	Remote Similarity	NPC276093
0.5655	Remote Similarity	NPC477464
0.5649	Remote Similarity	NPC36831
0.5625	Remote Similarity	NPC489209
0.56	Remote Similarity	NPC473343
0.56	Remote Similarity	NPC76497
0.5592	Remote Similarity	NPC45606
0.5591	Remote Similarity	NPC40775
0.5591	Remote Similarity	NPC488526
0.5581	Remote Similarity	NPC134835
0.5546	Remote Similarity	NPC128925
0.553	Remote Similarity	NPC473826
0.5522	Remote Similarity	NPC268184
0.552	Remote Similarity	NPC470512
0.552	Remote Similarity	NPC157868
0.5515	Remote Similarity	NPC309907
0.5504	Remote Similarity	NPC481082
0.5504	Remote Similarity	NPC164419
0.5489	Remote Similarity	NPC470915
0.5455	Remote Similarity	NPC96641
0.5455	Remote Similarity	NPC163183
0.5455	Remote Similarity	NPC220838
0.5443	Remote Similarity	NPC23020
0.5441	Remote Similarity	NPC475899
0.5441	Remote Similarity	NPC323341
0.544	Remote Similarity	NPC173583
0.5435	Remote Similarity	NPC47995
0.542	Remote Similarity	NPC73318
0.5414	Remote Similarity	NPC478559
0.5414	Remote Similarity	NPC478560
0.5385	Remote Similarity	NPC237503
0.5385	Remote Similarity	NPC257468
0.5345	Remote Similarity	NPC167383
0.5344	Remote Similarity	NPC469821
0.5338	Remote Similarity	NPC187618
0.5338	Remote Similarity	NPC69811
0.5317	Remote Similarity	NPC58448
0.5317	Remote Similarity	NPC127056
0.5315	Remote Similarity	NPC135849

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC4328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7903
0.1-0.2	1190
0.2-0.3	52
0.3-0.4	5
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