NPASS Compound

Natural Product: NPC575236

Natural Product ID	NPC575236
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(9,10,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaen-21-yl) acetate
IUPAC Name	(9,10,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaen-21-yl) acetate
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 90 96 0 0 0 0 0 0 0 0999 V2000 -4.7934 3.6157 -3.0217 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8458 3.1232 -2.1271 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8852 1.8874 -1.4940 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9295 1.0193 -1.7273 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8928 -0.1837 -1.0613 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8309 -0.4951 -0.1869 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8237 0.4057 0.0054 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8314 1.6168 -0.6468 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7994 2.5001 -0.4325 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8192 2.4234 0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3098 1.6616 0.3429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2694 1.5877 1.2796 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1030 2.3111 2.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 3.0827 2.7176 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9441 3.1115 1.7106 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1178 3.8750 1.8543 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1200 5.1877 1.4202 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3250 6.0627 1.5391 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0669 5.6413 0.9130 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4962 0.7895 1.1282 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8950 0.4843 -0.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8230 -0.7147 -0.3158 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1148 -0.4613 0.0991 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0587 -1.4998 0.0942 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6690 -2.7466 -0.3257 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5837 -3.7981 -0.3412 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9209 -3.6503 0.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3583 -2.9632 -0.7374 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0022 -4.2412 -1.1567 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1490 -4.5698 -2.5318 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4211 -1.9523 -0.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1778 -2.2294 -1.1499 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9688 -2.2467 -0.5649 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1643 -2.1748 -1.3627 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4031 -2.1903 -0.7524 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5279 -2.2740 0.6125 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4184 -2.3455 1.3924 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8202 -2.3316 0.7984 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8519 -2.2708 1.2933 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9572 -1.8253 0.4275 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2379 -1.8946 1.0705 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4167 -2.9619 1.9937 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3449 -1.6386 0.2114 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9224 -1.2494 -1.1821 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5753 0.8840 0.5497 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8118 1.9417 -0.1446 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6385 1.5406 -0.8653 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8996 2.7119 -1.2151 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7711 2.9972 -3.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8016 3.6395 -2.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4883 4.6509 -3.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7506 1.2386 -2.3914 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0271 0.1507 0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4130 1.1050 -0.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9049 2.2329 3.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1435 3.6450 3.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9587 7.1135 1.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9808 5.7998 2.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9394 6.0084 0.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3555 1.3087 1.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4076 -0.1562 1.7495 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0662 0.2206 -0.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0785 -1.2694 0.4296 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5795 -4.4278 -0.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3728 -2.6846 -0.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9627 -3.8130 1.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6404 -3.7749 -3.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2425 -4.5957 -2.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6765 -5.5666 -2.6700 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0978 -2.1084 -2.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2938 -2.1337 -1.3745 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5239 -2.4115 2.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6726 -2.3967 1.4751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8047 -1.7545 2.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0442 -3.3529 1.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0208 -2.5810 -0.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4741 -2.9223 2.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2443 -3.9651 1.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8062 -2.7734 2.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9794 -2.5510 0.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9544 -0.8285 0.6626 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8458 -0.8503 -1.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5363 -2.1389 -1.7171 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6647 1.0142 0.2199 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6553 0.9699 1.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4406 2.6592 0.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4650 2.6105 -0.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5723 3.3107 -0.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0384 2.4105 -1.8457 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4818 3.4145 -1.8561 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 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 17 18 1 0 17 19 2 0 12 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 28 31 2 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 23 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 8 3 1 0 15 10 1 0 47 21 1 0 44 5 1 0 40 6 1 0 31 22 1 0 38 33 1 0 1 49 1 0 1 50 1 0 1 51 1 0 4 52 1 0 7 53 1 0 11 54 1 0 13 55 1 0 14 56 1 0 18 57 1 0 18 58 1 0 18 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 24 63 1 0 27 64 1 0 27 65 1 0 27 66 1 0 30 67 1 0 30 68 1 0 30 69 1 0 34 70 1 0 35 71 1 0 37 72 1 0 38 73 1 0 39 74 1 0 39 75 1 0 40 76 1 0 42 77 1 0 42 78 1 0 42 79 1 0 43 80 1 0 43 81 1 0 44 82 1 0 44 83 1 0 45 84 1 0 45 85 1 0 46 86 1 0 46 87 1 0 48 88 1 0 48 89 1 0 48 90 1 0 M END

Standard InCHIKey	PXGMERUJAUULHY-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C39H42N2O7/c1-23(42)46-32-12-9-25-18-31-37-27(14-16-41(31)3)21-36(44-5)38(45-6)39(37)47-28-10-7-24(8-11-28)17-30-29-22-35(48-34(32)19-25)33(43-4)20-26(29)13-15-40(30)2/h7-12,19-22,30-31H,13-18H2,1-6H3
SMILES	COC1=CC2=C3C=C1OC1=CC(=CC=C1OC(C)=O)CC1C4=C(C=C(OC)C(OC)=C4OC4=CC=C(C=C4)CC3N(C)CC2)CCN1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.3	Volume:	672.456 ? Van der Waals volume.
Dense:	0.967	LogP:	3.3 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.231 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.453 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	43.0
TPSA:	78.93 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	8.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.17	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.823	Fsp³:	0.359
MCE-18:	132.075 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.988	Fluc inhibitor:	0.096 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.578 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.793 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.147

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.678	MDCK Permeability:	-4.703
Pgp-inhibitor:	0.728	Pgp-substrate:	0.336
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%):	0.018	30% Bioavailability (F30%):	0.022
50% Bioavailability (F50%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998	MRP1:	0.994
Plasma Protein Binding (PPB):	79.279%	Volume Distribution (VD):	0.331
Fu:	21.687% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.185
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.564
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.527	CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.976	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.446	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.769	CYP2C8-inhibitor:	0.008
HLM stability:	0.404 ? 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):

7.833

Half-life (T1/2):

1.55

ADMET: Toxicity

hERG Blockers:	0.82	hERG Blockers (10um):	0.801
Human Hepatotoxicity (H-HT):	0.308	Drug-induced Liver Injury (DILI):	0.005
AMES Toxicity:	0.625	Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.882	Skin Sensitization:	0.971
Carcinogencity:	0.691	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.893
Drug-induced Neurotoxicity:	0.5	Ototoxicity:	0.842
Hematotoxicity:	0.069	Drug-induced Nephrotoxicity:	0.02
Genotoxicity:	0.156	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.294	Hek293 Cytotoxicity:	0.74
BCF:	1.612 ? 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:	4.364 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.92 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.248 ? 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
NPO40796	Berberis brevissima	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32364734]
NPO40796	Berberis brevissima	Species	Berberidaceae	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 NPC575236 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	31849
0.1-0.2	17321
0.2-0.3	462
0.3-0.4	96
0.4-0.5	34
0.5-0.6	45
0.6-0.7	24
0.7-0.8	1
0.8-0.85	1
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC480587
0.8657	High Similarity	NPC76682
0.8657	High Similarity	NPC10908
0.8657	High Similarity	NPC63646
0.8657	High Similarity	NPC317145
0.8657	High Similarity	NPC198498
0.8657	High Similarity	NPC115284
0.8261	Intermediate Similarity	NPC276890
0.7568	Intermediate Similarity	NPC73492
0.7568	Intermediate Similarity	NPC299990
0.75	Intermediate Similarity	NPC223690
0.75	Intermediate Similarity	NPC9532
0.7397	Intermediate Similarity	NPC227060
0.7385	Intermediate Similarity	NPC317439
0.7368	Intermediate Similarity	NPC239824
0.7297	Intermediate Similarity	NPC12424
0.7297	Intermediate Similarity	NPC129518
0.7297	Intermediate Similarity	NPC251580
0.7273	Intermediate Similarity	NPC185639
0.7273	Intermediate Similarity	NPC251735
0.7273	Intermediate Similarity	NPC49075
0.7273	Intermediate Similarity	NPC599951
0.72	Intermediate Similarity	NPC603853
0.7059	Intermediate Similarity	NPC247639
0.7059	Intermediate Similarity	NPC25084
0.7013	Intermediate Similarity	NPC279228
0.6923	Remote Similarity	NPC311973
0.6883	Remote Similarity	NPC290582
0.6883	Remote Similarity	NPC217748
0.6883	Remote Similarity	NPC182052
0.6883	Remote Similarity	NPC271013
0.6883	Remote Similarity	NPC42663
0.6883	Remote Similarity	NPC15414
0.6835	Remote Similarity	NPC116465
0.6588	Remote Similarity	NPC480586
0.6588	Remote Similarity	NPC480590
0.6429	Remote Similarity	NPC24260
0.642	Remote Similarity	NPC254441
0.6364	Remote Similarity	NPC41376
0.631	Remote Similarity	NPC475479
0.631	Remote Similarity	NPC323537
0.6235	Remote Similarity	NPC485712
0.619	Remote Similarity	NPC16357
0.619	Remote Similarity	NPC302245
0.619	Remote Similarity	NPC195538
0.6145	Remote Similarity	NPC229373
0.6118	Remote Similarity	NPC212237
0.6118	Remote Similarity	NPC243454
0.6076	Remote Similarity	NPC603603
0.6047	Remote Similarity	NPC611658
0.5952	Remote Similarity	NPC274716
0.5952	Remote Similarity	NPC167116
0.5952	Remote Similarity	NPC609821
0.5934	Remote Similarity	NPC475597
0.5909	Remote Similarity	NPC10871
0.5882	Remote Similarity	NPC181796
0.5882	Remote Similarity	NPC290005
0.5882	Remote Similarity	NPC54654
0.5882	Remote Similarity	NPC7715
0.5882	Remote Similarity	NPC328155
0.5882	Remote Similarity	NPC222661
0.5882	Remote Similarity	NPC285931
0.5604	Remote Similarity	NPC206900
0.5604	Remote Similarity	NPC281581
0.5543	Remote Similarity	NPC485711
0.5529	Remote Similarity	NPC475393
0.5513	Remote Similarity	NPC317272
0.5513	Remote Similarity	NPC268503
0.5507	Remote Similarity	NPC213206
0.5507	Remote Similarity	NPC188163
0.5507	Remote Similarity	NPC328750
0.55	Remote Similarity	NPC256012
0.55	Remote Similarity	NPC610965
0.5443	Remote Similarity	NPC30779
0.5385	Remote Similarity	NPC239584
0.5362	Remote Similarity	NPC314682
0.5357	Remote Similarity	NPC480591
0.5349	Remote Similarity	NPC286119
0.5349	Remote Similarity	NPC112248
0.5333	Remote Similarity	NPC249996
0.5269	Remote Similarity	NPC82457
0.5263	Remote Similarity	NPC41122
0.5263	Remote Similarity	NPC318805
0.5233	Remote Similarity	NPC608819
0.5165	Remote Similarity	NPC8836
0.5111	Remote Similarity	NPC302275
0.5106	Remote Similarity	NPC11296
0.5106	Remote Similarity	NPC274661
0.5065	Remote Similarity	NPC104196
0.506	Remote Similarity	NPC480592
0.5059	Remote Similarity	NPC240841
0.5055	Remote Similarity	NPC139783
0.5055	Remote Similarity	NPC65312
0.5055	Remote Similarity	NPC611798
0.505	Remote Similarity	NPC475654

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC575236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4666
0.1-0.2	4347
0.2-0.3	123
0.3-0.4	6
0.4-0.5	3
0.5-0.6	2
0.6-0.7	0
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8657	High Similarity	NPD8099	Discontinued
0.8169	Intermediate Similarity	NPD8156	Discontinued
0.7105	Intermediate Similarity	NPD8095	Phase 1
0.5507	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5052	Remote Similarity	NPD8053	Approved

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