NPASS Compound

Natural Product: NPC471524

Natural Product ID	NPC471524
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cochinchinenin C
IUPAC Name	3-[4-hydroxy-5-[3-(4-hydroxy-2-methoxyphenyl)-1-(4-methoxyphenyl)propyl]-2-methoxyphenyl]-1-(4-hydroxyphenyl)propan-1-one
Synonyms	cochinchinenin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL254649
PubChem CID	23634528
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

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 74 77 0 0 0 0 0 0 0 0999 V2000 -4.0773 6.7416 -1.7947 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4422 5.7755 -0.8305 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7089 4.6061 -0.7237 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6347 4.4016 -1.5588 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9213 3.2338 -1.4345 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2423 2.2438 -0.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3114 2.4487 0.3359 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0289 3.6266 0.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3815 1.0642 -0.5059 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9035 -0.1609 0.1466 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1778 -0.6802 -0.4706 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6446 -1.9116 0.2235 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0021 -3.1011 -0.0306 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4160 -4.2373 0.5940 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4680 -4.2338 1.4812 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1316 -3.0354 1.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6976 -1.8911 1.1072 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8675 -5.4125 2.1042 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9313 -3.1848 -0.9143 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2539 -4.3705 -1.1991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0677 1.4205 0.1110 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0260 1.7473 1.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1713 2.0790 2.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3355 2.0904 1.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2846 1.7603 -0.0036 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0868 1.4198 -0.6401 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5110 1.6523 -0.8107 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0045 0.2766 -0.9462 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3670 -0.5090 0.1992 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 -0.1501 1.3781 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8886 -1.8909 -0.0317 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2499 -2.6930 1.0226 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7318 -3.9666 0.8436 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8600 -4.4628 -0.4242 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5043 -3.6781 -1.4995 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0157 -2.3839 -1.2983 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3499 -5.7624 -0.6533 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5214 2.4551 1.9916 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4935 2.7839 3.3611 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1809 1.7595 2.2478 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0605 6.2444 -2.7867 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7788 7.6058 -1.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0716 7.1833 -1.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3600 5.1557 -2.3030 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0788 3.1144 -2.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5841 1.6935 1.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8798 3.8235 0.8467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1986 0.7957 -1.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0429 -0.1259 1.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1323 -0.9671 -0.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9528 -1.0244 -1.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9850 0.0370 -0.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8861 -5.1796 0.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9542 -3.0549 2.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2362 -0.9654 1.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8540 -5.4849 2.3621 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9220 -5.0963 -1.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9668 -4.8425 -0.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3128 -4.2316 -1.7397 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1681 2.3343 3.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0362 1.1636 -1.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 2.3411 -0.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3410 2.1315 -1.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9072 0.3154 -1.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2876 -0.3585 -1.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1472 -2.2981 2.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0075 -4.5706 1.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6135 -4.0934 -2.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7461 -1.7966 -2.1747 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1289 -6.0325 -0.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4994 3.2349 3.5864 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7175 3.5561 3.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3487 1.9088 4.0184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1102 1.6128 3.2399 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 6 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 15 18 1 0 13 19 1 0 19 20 1 0 9 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 24 38 1 0 38 39 1 0 22 40 1 0 8 3 1 0 17 12 1 0 26 21 1 0 36 31 1 0 1 41 1 0 1 42 1 0 1 43 1 0 4 44 1 0 5 45 1 0 7 46 1 0 8 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 14 53 1 0 16 54 1 0 17 55 1 0 18 56 1 0 20 57 1 0 20 58 1 0 20 59 1 0 23 60 1 0 26 61 1 0 27 62 1 0 27 63 1 0 28 64 1 0 28 65 1 0 32 66 1 0 33 67 1 0 35 68 1 0 36 69 1 0 37 70 1 0 39 71 1 0 39 72 1 0 39 73 1 0 40 74 1 0 M END

Standard InCHIKey	SLJWKFROLINAGW-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C33H34O7/c1-38-27-14-7-21(8-15-27)28(16-9-23-6-13-26(35)19-32(23)39-2)29-18-24(33(40-3)20-31(29)37)10-17-30(36)22-4-11-25(34)12-5-22/h4-8,11-15,18-20,28,34-35,37H,9-10,16-17H2,1-3H3
SMILES	COC1=CC=C(C=C1)C(CCC2=C(C=C(C=C2)O)OC)C3=C(C=C(C(=C3)CCC(=O)C4=CC=C(C=C4)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	542.23	Volume:	572.356 ? Van der Waals volume.
Dense:	0.947	LogP:	5.278 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.882 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.623 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	25.0
TPSA:	105.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.178	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.074	Fsp³:	0.242
MCE-18:	50.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.627 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.127 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.591 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.31	Promiscuous compounds:	0.07

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814	MDCK Permeability:	-4.815
Pgp-inhibitor:	0.874	Pgp-substrate:	0.0
PAMPA:	0.001 ? 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):	0.001
20% Bioavailability (F20%):	0.055	30% Bioavailability (F30%):	0.794
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.11
Plasma Protein Binding (PPB):	97.74%	Volume Distribution (VD):	0.504
Fu:	2.511% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.975
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.962	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.969	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.994	CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.73	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.021	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? 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):

6.977

Half-life (T1/2):

1.317

ADMET: Toxicity

hERG Blockers:	0.831	hERG Blockers (10um):	0.852
Human Hepatotoxicity (H-HT):	0.765	Drug-induced Liver Injury (DILI):	0.046
AMES Toxicity:	0.135	Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.974	Skin Sensitization:	0.017
Carcinogencity:	0.307	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.758
Drug-induced Neurotoxicity:	0.64	Ototoxicity:	0.703
Hematotoxicity:	0.211	Drug-induced Nephrotoxicity:	0.68
Genotoxicity:	0.925	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.547	Hek293 Cytotoxicity:	0.964
BCF:	1.642 ? 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:	5.174 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.973 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.628 ? 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
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12016928]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	stems	Ningming County, Guangxi autonomous region, China	2006-Jan	PMID[17883259]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21661731]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	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
deltaG	3
deltaH	1
K	3
Kq	3
KSV	3
Activity	1
MIC	1

Activity Type	# Activity
Individual protein	16
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1592	Individual protein	Dipeptidyl peptidase IV	Homo sapiens	IC50	>	36900.0	nM	Open TG-GATES in vivo data: Pathology
NPT670	Individual protein	Thrombin	Homo sapiens	IC50	>	9200.0	nM	PMID[24571273]
NPT604	Individual protein	Serum albumin	Homo sapiens	deltaG	=	-31.09	kJ/mol	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	deltaH	=	-55.94	kJ/mol	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	K	=	12.32	10'4/M	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	K	=	18.62	10'4/M	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	K	=	25.32	10'4/M	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	Kq	=	12.15	10'12/M/s	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	Kq	=	14.95	10'12/M/s	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	Kq	=	17.69	10'12/M/s	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	KSV	=	12.15	10'4/M	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	KSV	=	14.95	10'4/M	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	KSV	=	17.69	10'4/M	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	deltaG	=	-30.67	kJ/mol	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	deltaG	=	-30.26	kJ/mol	PMID[25734332]
NPT604	Individual protein	Serum albumin	Homo sapiens	Activity	=	14.0	%	PMID[25443644]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	29500.0	nM	PMID[16417306]

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 NPC471524 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	26091
0.1-0.2	20485
0.2-0.3	3096
0.3-0.4	163
0.4-0.5	13
0.5-0.6	6
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9153	High Similarity	NPC471473
0.7121	Intermediate Similarity	NPC471523
0.6552	Remote Similarity	NPC309717
0.5714	Remote Similarity	NPC471517
0.5556	Remote Similarity	NPC112192
0.5467	Remote Similarity	NPC473309
0.52	Remote Similarity	NPC471522
0.5156	Remote Similarity	NPC189106
0.5079	Remote Similarity	NPC128348

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4728
0.1-0.2	4300
0.2-0.3	117
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