NPASS Compound

Natural Product: NPC571951

Natural Product ID	NPC571951
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{S})-1-[[4-[2-hydroxy-5-[[(1~{R})-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-1-yl]methyl]phenoxy]phenyl]methyl]-7-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-6-ol
IUPAC Name	(1~{S})-1-[[4-[2-hydroxy-5-[[(1~{R})-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-1-yl]methyl]phenoxy]phenyl]methyl]-7-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-6-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 84 89 0 0 0 0 0 0 0 0999 V2000 10.4996 1.3011 1.7356 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9885 1.6857 0.4706 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6826 1.3564 0.1150 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8911 0.6453 1.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6166 0.3211 0.6816 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1250 0.7058 -0.5675 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8937 1.4079 -1.4732 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1977 1.7369 -1.1193 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0191 2.4419 -1.9881 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7205 0.2959 -0.8330 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2208 0.7116 -2.1741 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8010 0.2326 -2.2985 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5451 -1.0072 -2.8180 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2342 -1.4340 -2.9245 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1707 -0.6583 -2.5270 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1522 -1.1177 -2.6482 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4124 0.6011 -1.9979 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6324 1.3931 -1.5954 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5302 1.0777 -0.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3465 -0.0572 0.1542 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2526 -0.3664 1.1530 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3498 0.4457 1.4190 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2928 0.1187 2.4905 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4193 -0.8099 2.1039 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3046 -0.3371 1.0557 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8063 0.9800 1.0733 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6490 1.4334 0.0937 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1320 2.7385 0.1318 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7678 3.6120 1.1686 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0358 0.6100 -0.9482 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9003 1.1437 -1.9144 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5687 -0.6580 -0.9883 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7044 -1.1213 0.0180 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2446 -2.5261 -0.0871 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9029 -2.6277 0.5887 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9341 -2.1330 1.9282 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6234 -3.0986 2.7614 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5096 1.5745 0.6547 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6033 1.9029 -0.3599 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7361 1.0101 -1.9000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6828 -1.1396 -0.6267 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6841 -1.7939 -1.4852 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0100 -1.4862 0.7145 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6597 -0.4276 1.5377 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6559 0.1989 1.7892 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8132 1.5645 2.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4532 1.8368 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2603 0.3399 1.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4772 1.6906 -2.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0290 2.3758 -1.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0739 0.7515 -0.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8406 0.4012 -3.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1668 1.8223 -2.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3265 -1.6906 -3.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0440 -2.4201 -3.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5359 -1.0841 -3.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4914 -0.6816 -0.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0711 -1.2684 1.7196 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7096 -0.4432 3.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6954 1.0079 3.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0659 -0.8482 3.0475 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4771 1.5803 1.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6696 3.8560 1.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3464 4.5634 1.0024 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9721 3.2029 2.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7382 1.5842 -1.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8505 -1.3187 -1.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0895 -2.7455 -1.1716 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9832 -3.2425 0.3222 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1783 -2.1275 -0.0563 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6795 -3.7266 0.6533 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6057 -3.3802 2.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6669 -2.7407 3.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9521 -4.0068 2.7860 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3125 2.2877 0.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7348 2.7934 -0.9587 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9278 2.0011 -1.4837 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6244 -1.4268 -2.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6918 -1.7021 -1.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4303 -2.8770 -1.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0559 -1.7827 1.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6577 -2.4051 0.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2266 -0.9233 2.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9415 0.2997 1.9714 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 6 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 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 2 0 30 31 1 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 22 38 1 0 38 39 2 0 17 40 2 0 10 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 8 3 1 0 40 12 1 0 44 5 1 0 39 19 1 0 36 24 1 0 33 25 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 7 49 1 0 9 50 1 0 10 51 1 1 11 52 1 0 11 53 1 0 13 54 1 0 14 55 1 0 16 56 1 0 20 57 1 0 21 58 1 0 23 59 1 0 23 60 1 0 24 61 1 1 26 62 1 0 29 63 1 0 29 64 1 0 29 65 1 0 31 66 1 0 32 67 1 0 34 68 1 0 34 69 1 0 35 70 1 0 35 71 1 0 37 72 1 0 37 73 1 0 37 74 1 0 38 75 1 0 39 76 1 0 40 77 1 0 42 78 1 0 42 79 1 0 42 80 1 0 43 81 1 0 43 82 1 0 44 83 1 0 44 84 1 0 M END

Standard InCHIKey	RMABHGZZUIKESI-XZWHSSHBSA-N
Standard InCHI	InChI=1S/C36H40N2O6/c1-37-13-11-24-18-32(40)35(43-4)21-28(24)29(37)15-22-5-8-26(9-6-22)44-36-17-23(7-10-31(36)39)16-30-27-20-33(41)34(42-3)19-25(27)12-14-38(30)2/h5-10,17-21,29-30,39-41H,11-16H2,1-4H3/t29-,30+/m0/s1
SMILES	COC1=CC2=C(C=C1O)[C@@H](CC1=CC=C(O)C(OC3=CC=C(C[C@H]4C5=CC(OC)=C(O)C=C5CCN4C)C=C3)=C1)N(C)CC2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.29	Volume:	622.971 ? Van der Waals volume.
Dense:	0.957	LogP:	3.009 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.619 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.059 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	34.0
TPSA:	94.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.223	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.685	Fsp³:	0.333
MCE-18:	113.75 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.987	Fluc inhibitor:	0.189 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.887 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.953 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.187

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.141	MDCK Permeability:	-4.791
Pgp-inhibitor:	0.807	Pgp-substrate:	0.011
PAMPA:	0.003 ? 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%):	0.986	30% Bioavailability (F30%):	0.821
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366	MRP1:	0.991
Plasma Protein Binding (PPB):	63.935%	Volume Distribution (VD):	-0.169
Fu:	40.082% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.836
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.994	CYP2C8-inhibitor:	0.058
HLM stability:	0.723 ? 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):

5.672

Half-life (T1/2):

2.862

ADMET: Toxicity

hERG Blockers:	0.846	hERG Blockers (10um):	0.753
Human Hepatotoxicity (H-HT):	0.905	Drug-induced Liver Injury (DILI):	0.141
AMES Toxicity:	0.767	Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	0.552
Carcinogencity:	0.395	Eye Corrosion:	0.0
Eye Irritation:	0.051	Respiratory Toxicity:	0.535
Drug-induced Neurotoxicity:	0.858	Ototoxicity:	0.916
Hematotoxicity:	0.052	Drug-induced Nephrotoxicity:	0.258
Genotoxicity:	0.965	RPMI-8226 Immunitoxicity:	0.08
A549 Cytotoxicity:	0.398	Hek293 Cytotoxicity:	0.926
BCF:	1.736 ? 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:	4.468 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.559 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.011 ? 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
NPO17091	Berberis chilensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO51969	Berberis laurina Billb.	Genus	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17091	Berberis chilensis	Species	Berberidaceae	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 NPC571951 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	27265
0.1-0.2	20286
0.2-0.3	1878
0.3-0.4	270
0.4-0.5	71
0.5-0.6	44
0.6-0.7	25
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9077	High Similarity	NPC240841
0.8	Intermediate Similarity	NPC317272
0.8	Intermediate Similarity	NPC268503
0.7794	Intermediate Similarity	NPC480592
0.7465	Intermediate Similarity	NPC610959
0.7324	Intermediate Similarity	NPC603603
0.7031	Intermediate Similarity	NPC321505
0.7031	Intermediate Similarity	NPC179825
0.7013	Intermediate Similarity	NPC181796
0.7013	Intermediate Similarity	NPC54654
0.7013	Intermediate Similarity	NPC7715
0.7013	Intermediate Similarity	NPC328155
0.7013	Intermediate Similarity	NPC222661
0.7013	Intermediate Similarity	NPC285931
0.6933	Remote Similarity	NPC608819
0.6875	Remote Similarity	NPC191376
0.6875	Remote Similarity	NPC147390
0.6875	Remote Similarity	NPC428
0.6795	Remote Similarity	NPC290005
0.6753	Remote Similarity	NPC185639
0.6753	Remote Similarity	NPC251735
0.6753	Remote Similarity	NPC49075
0.6753	Remote Similarity	NPC599951
0.6667	Remote Similarity	NPC274716
0.6667	Remote Similarity	NPC167116
0.6667	Remote Similarity	NPC256012
0.6667	Remote Similarity	NPC609821
0.6667	Remote Similarity	NPC610965
0.6623	Remote Similarity	NPC286119
0.6543	Remote Similarity	NPC611658
0.6538	Remote Similarity	NPC223690
0.6538	Remote Similarity	NPC9532
0.642	Remote Similarity	NPC212237
0.642	Remote Similarity	NPC601489
0.642	Remote Similarity	NPC604804
0.6341	Remote Similarity	NPC24260
0.6341	Remote Similarity	NPC8836
0.6029	Remote Similarity	NPC135538
0.6029	Remote Similarity	NPC24233
0.5926	Remote Similarity	NPC254441
0.5802	Remote Similarity	NPC311973
0.5802	Remote Similarity	NPC239824
0.5802	Remote Similarity	NPC600872
0.5775	Remote Similarity	NPC104196
0.5775	Remote Similarity	NPC247639
0.5775	Remote Similarity	NPC25084
0.575	Remote Similarity	NPC290582
0.575	Remote Similarity	NPC217748
0.575	Remote Similarity	NPC182052
0.575	Remote Similarity	NPC271013
0.575	Remote Similarity	NPC42663
0.575	Remote Similarity	NPC15414
0.5732	Remote Similarity	NPC601503
0.5679	Remote Similarity	NPC279228
0.5679	Remote Similarity	NPC609914
0.5667	Remote Similarity	NPC41122
0.5667	Remote Similarity	NPC318805
0.561	Remote Similarity	NPC600054
0.561	Remote Similarity	NPC601504
0.5604	Remote Similarity	NPC60295
0.5588	Remote Similarity	NPC185838
0.5543	Remote Similarity	NPC201508
0.5506	Remote Similarity	NPC473589
0.5376	Remote Similarity	NPC175890
0.5357	Remote Similarity	NPC116465
0.5325	Remote Similarity	NPC30779
0.5224	Remote Similarity	NPC314682
0.5222	Remote Similarity	NPC480590
0.5165	Remote Similarity	NPC206900
0.5147	Remote Similarity	NPC213206
0.5147	Remote Similarity	NPC188163
0.5147	Remote Similarity	NPC328750
0.5125	Remote Similarity	NPC76682
0.5125	Remote Similarity	NPC10908
0.5125	Remote Similarity	NPC63646
0.5125	Remote Similarity	NPC317145
0.5125	Remote Similarity	NPC198498
0.5125	Remote Similarity	NPC115284
0.5116	Remote Similarity	NPC229373
0.5106	Remote Similarity	NPC191132
0.5062	Remote Similarity	NPC276890
0.5056	Remote Similarity	NPC605743
0.5055	Remote Similarity	NPC480586

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC571951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4209
0.1-0.2	4781
0.2-0.3	146
0.3-0.4	7
0.4-0.5	2
0.5-0.6	5
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
0.5889	Remote Similarity	NPD8054	Phase 4
0.5604	Remote Similarity	NPD8053	Approved
0.527	Remote Similarity	NPD4010	Discontinued
0.5147	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5125	Remote Similarity	NPD8099	Discontinued

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