NPASS Compound

Natural Product: NPC531615

Natural Product ID	NPC531615
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-[[3-hydroxy-4-[[(1~{R})-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-7-yl]oxy]phenyl]methyl]-6-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-7-ol
IUPAC Name	(1~{S})-1-[[3-hydroxy-4-[[(1~{R})-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-7-yl]oxy]phenyl]methyl]-6-methoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-7-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 -10.9855 1.2499 1.8174 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3760 0.0626 1.3436 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0020 0.0778 1.0646 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2591 1.2328 1.2505 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8886 1.2256 0.9653 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2713 0.0822 0.5018 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9946 -1.0693 0.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3714 -1.0645 0.5984 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0919 -2.2351 0.4032 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8205 0.2210 0.2512 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1348 -0.9801 -0.2646 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6997 -0.6630 -0.4628 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7481 -0.8725 0.5124 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4359 -0.5832 0.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0461 -0.0273 -0.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3453 0.2255 -0.9688 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5173 0.0086 -1.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5467 -0.5754 -0.6904 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7881 -0.8375 -1.1503 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0958 -0.5309 -2.4977 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1662 0.0186 -3.3150 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8875 0.2788 -2.8006 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0233 0.8393 -3.7033 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2935 1.1599 -5.0292 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4752 -0.8810 -2.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7232 -2.3111 -2.5067 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2860 -2.6348 -1.1690 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3782 -3.3189 -0.5017 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8981 -1.4281 -0.4382 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9816 -1.5403 1.0069 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9855 -0.2405 1.7073 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9060 0.3215 2.3216 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9551 1.5708 2.9501 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1122 2.2953 2.9761 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2024 3.5377 3.5885 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2215 1.7570 2.3664 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1640 0.5330 1.7528 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9052 0.1704 -1.8319 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6539 0.7047 -3.1023 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2526 -0.1325 -1.6468 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2710 0.7408 1.4932 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5910 -0.1259 2.6158 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7386 2.0868 1.7144 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0566 2.4340 1.1381 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6475 1.5255 2.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0861 1.1108 1.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7577 2.1246 1.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7472 2.1311 1.6156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4856 -1.9354 -0.0471 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3948 -2.7672 1.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6928 1.0352 -0.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6255 -1.2597 -1.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1729 -1.8543 0.4318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0880 -1.2978 1.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2965 -0.7545 1.1220 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2538 -0.8075 0.2971 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4206 0.2518 -4.3610 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5101 1.8287 -5.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4419 0.2413 -5.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2413 1.7552 -5.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5040 -0.9112 -4.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2271 -0.1632 -2.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8373 -2.4616 -2.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2756 -2.9916 -3.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7304 -4.1070 -1.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2434 -2.6394 -0.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0799 -3.8451 0.4030 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8020 -0.7294 -0.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9978 -1.9919 1.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2835 -2.2682 1.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9628 -0.2120 2.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0842 1.9904 3.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0398 4.0956 3.4873 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1555 2.2897 2.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0310 0.0770 1.2577 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0048 1.6133 -3.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0057 0.0381 -2.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9359 0.1892 3.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6717 -0.0429 2.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2970 -1.1547 2.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7555 2.2655 2.8098 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9446 2.7815 1.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9749 2.9058 0.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5804 3.1617 1.7977 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 16 17 1 0 17 18 2 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 20 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 34 36 1 0 36 37 2 0 15 38 1 0 38 39 1 0 38 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 22 17 1 0 37 31 1 0 29 19 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 6 11 52 1 0 11 53 1 0 13 54 1 0 14 55 1 0 18 56 1 0 21 57 1 0 24 58 1 0 24 59 1 0 24 60 1 0 25 61 1 0 25 62 1 0 26 63 1 0 26 64 1 0 28 65 1 0 28 66 1 0 28 67 1 0 29 68 1 6 30 69 1 0 30 70 1 0 32 71 1 0 33 72 1 0 35 73 1 0 36 74 1 0 37 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	MXVKZTHARDQLEC-IHLOFXLRSA-N
Standard InCHI	InChI=1S/C36H40N2O6/c1-37-14-12-25-19-35(43-4)36(21-28(25)29(37)15-22-5-8-26(39)9-6-22)44-33-10-7-23(17-31(33)40)16-30-27-20-32(41)34(42-3)18-24(27)11-13-38(30)2/h5-10,17-21,29-30,39-41H,11-16H2,1-4H3/t29-,30+/m1/s1
SMILES	COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(OC3=CC4=C(C=C3OC)CCN(C)[C@@H]4CC3=CC=C(O)C=C3)C(O)=C1)N(C)CC2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.29	Volume:	622.971 ? Van der Waals volume.
Dense:	0.957	LogP:	2.377 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.342 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.512 ? 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:	3.703	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:	0.104 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.8 ? 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:	0.147

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.071	MDCK Permeability:	-4.805
Pgp-inhibitor:	0.485	Pgp-substrate:	0.923
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):	0.0
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	0.94
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.761	MRP1:	0.993
Plasma Protein Binding (PPB):	57.141%	Volume Distribution (VD):	-0.231
Fu:	44.704% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.887	BCRP inhibitor:	0.534
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.149
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.985	CYP3A4-substrate:	0.804
CYP2B6-substrate:	0.177	CYP2C8-inhibitor:	0.188
HLM stability:	0.656 ? 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):

7.769

Half-life (T1/2):

2.888

ADMET: Toxicity

hERG Blockers:	0.926	hERG Blockers (10um):	0.771
Human Hepatotoxicity (H-HT):	0.92	Drug-induced Liver Injury (DILI):	0.006
AMES Toxicity:	0.4	Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	0.233
Carcinogencity:	0.073	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.984
Drug-induced Neurotoxicity:	0.994	Ototoxicity:	0.334
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.379
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.396	Hek293 Cytotoxicity:	0.794
BCF:	1.56 ? 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:	4.366 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.249 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.784 ? 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
NPO52009	Cyclea sutchuensis	Genus	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC531615 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	27917
0.1-0.2	19429
0.2-0.3	2152
0.3-0.4	202
0.4-0.5	72
0.5-0.6	46
0.6-0.7	25
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8676	High Similarity	NPC610959
0.75	Intermediate Similarity	NPC321505
0.75	Intermediate Similarity	NPC179825
0.7465	Intermediate Similarity	NPC480592
0.7237	Intermediate Similarity	NPC600872
0.7215	Intermediate Similarity	NPC601489
0.7215	Intermediate Similarity	NPC604804
0.7162	Intermediate Similarity	NPC240841
0.7083	Intermediate Similarity	NPC256012
0.7083	Intermediate Similarity	NPC610965
0.7077	Intermediate Similarity	NPC147390
0.7077	Intermediate Similarity	NPC428
0.7027	Intermediate Similarity	NPC603603
0.6818	Remote Similarity	NPC191376
0.6716	Remote Similarity	NPC135538
0.6716	Remote Similarity	NPC24233
0.6543	Remote Similarity	NPC290005
0.6515	Remote Similarity	NPC185838
0.641	Remote Similarity	NPC480591
0.6375	Remote Similarity	NPC600054
0.6375	Remote Similarity	NPC601504
0.6341	Remote Similarity	NPC181796
0.6341	Remote Similarity	NPC54654
0.6341	Remote Similarity	NPC7715
0.6341	Remote Similarity	NPC328155
0.6341	Remote Similarity	NPC222661
0.6341	Remote Similarity	NPC285931
0.6296	Remote Similarity	NPC223690
0.6296	Remote Similarity	NPC9532
0.6296	Remote Similarity	NPC601503
0.6216	Remote Similarity	NPC317272
0.6216	Remote Similarity	NPC268503
0.6173	Remote Similarity	NPC286119
0.6098	Remote Similarity	NPC185639
0.6098	Remote Similarity	NPC251735
0.6098	Remote Similarity	NPC49075
0.6098	Remote Similarity	NPC599951
0.6049	Remote Similarity	NPC609914
0.5976	Remote Similarity	NPC311973
0.5976	Remote Similarity	NPC239824
0.593	Remote Similarity	NPC611658
0.5926	Remote Similarity	NPC290582
0.5926	Remote Similarity	NPC217748
0.5926	Remote Similarity	NPC182052
0.5926	Remote Similarity	NPC271013
0.5926	Remote Similarity	NPC42663
0.5926	Remote Similarity	NPC15414
0.5854	Remote Similarity	NPC279228
0.5814	Remote Similarity	NPC212237
0.5747	Remote Similarity	NPC24260
0.5747	Remote Similarity	NPC605743
0.5714	Remote Similarity	NPC254441
0.5647	Remote Similarity	NPC274716
0.5647	Remote Similarity	NPC167116
0.5647	Remote Similarity	NPC609821
0.5568	Remote Similarity	NPC275680
0.5568	Remote Similarity	NPC22115
0.5541	Remote Similarity	NPC247639
0.5541	Remote Similarity	NPC25084
0.5529	Remote Similarity	NPC116465
0.5495	Remote Similarity	NPC206900
0.5476	Remote Similarity	NPC608819
0.5441	Remote Similarity	NPC314682
0.5417	Remote Similarity	NPC103379
0.5385	Remote Similarity	NPC480586
0.5341	Remote Similarity	NPC16357
0.5341	Remote Similarity	NPC302245
0.5319	Remote Similarity	NPC41122
0.5319	Remote Similarity	NPC318805
0.5309	Remote Similarity	NPC76682
0.5309	Remote Similarity	NPC10908
0.5309	Remote Similarity	NPC63646
0.5309	Remote Similarity	NPC317145
0.5309	Remote Similarity	NPC198498
0.5309	Remote Similarity	NPC115284
0.5217	Remote Similarity	NPC480590
0.5208	Remote Similarity	NPC201508
0.5161	Remote Similarity	NPC82457
0.5143	Remote Similarity	NPC213206
0.5143	Remote Similarity	NPC188163
0.5143	Remote Similarity	NPC328750
0.5072	Remote Similarity	NPC484289
0.506	Remote Similarity	NPC276890
0.5059	Remote Similarity	NPC603853

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC531615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4502
0.1-0.2	4478
0.2-0.3	155
0.3-0.4	8
0.4-0.5	0
0.5-0.6	6
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
0.587	Remote Similarity	NPD8054	Phase 4
0.5591	Remote Similarity	NPD8053	Approved
0.5309	Remote Similarity	NPD8099	Discontinued
0.5263	Remote Similarity	NPD4010	Discontinued
0.5143	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5059	Remote Similarity	NPD8156	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