NPASS Compound

Natural Product: NPC190031

Natural Product ID	NPC190031
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZKGBUDJODLZAHS-JSOSNVBQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	12305304
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

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 87 92 0 0 0 0 0 0 0 0999 V2000 5.2990 -2.1618 0.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8785 -0.7968 0.5142 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0285 -0.2711 1.8343 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3008 0.4438 2.1188 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3987 0.1335 1.1371 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7050 0.0641 1.5499 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6908 -0.2184 0.6335 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3014 -0.4241 -0.6967 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9863 -0.3473 -1.0764 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0008 -0.0667 -0.1702 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5730 0.0427 -0.4359 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1499 -0.1764 -1.8456 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6865 0.1204 -1.9508 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2131 1.3821 -2.2519 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8674 1.6775 -2.3482 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9336 0.6892 -2.1399 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3803 -0.5985 -1.8339 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7367 -0.8564 -1.7455 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4205 0.9203 -2.2197 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2833 1.1928 -1.1975 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3509 0.3157 -0.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2760 0.4903 0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1164 1.5977 0.8266 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0707 2.4698 0.6211 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1400 2.2901 -0.3840 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0859 3.2057 -0.5594 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0062 4.3099 0.3201 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3966 -0.4128 0.2805 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6822 -0.0717 -0.4431 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7169 -1.0569 -0.0764 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4640 -2.2814 0.4994 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4848 -3.1728 0.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7967 -2.8830 0.5315 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0825 -1.6549 -0.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0541 -0.7871 -0.3322 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3021 0.5673 -0.9289 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4977 1.5185 -0.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1022 1.2482 -0.0810 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5158 2.2286 -1.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8063 -3.8027 0.8401 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1362 -3.4242 0.5376 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1745 -4.3930 1.3741 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3174 -0.7065 -1.5992 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0244 -0.3027 0.9835 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5573 -0.1239 2.2606 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9622 -2.4315 -0.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3916 -2.8210 0.3782 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7905 -2.5019 1.4341 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1886 0.4144 2.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9214 -1.1312 2.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6924 0.1525 3.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1500 1.5307 2.1160 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9283 0.2390 2.6043 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7107 -0.5098 -2.0932 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2755 1.1015 -0.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6459 0.5435 -2.5298 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3129 -1.1732 -2.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9363 2.1656 -2.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6104 2.6957 -2.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6592 -1.3969 -1.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0378 -1.8683 -1.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4927 -0.5684 -1.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8240 1.7967 1.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9341 3.3521 1.2564 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8517 4.9332 0.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9586 4.8767 0.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0612 3.9052 1.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0397 -1.4319 -0.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5829 -0.5421 1.3595 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5155 -0.0463 -1.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4267 -2.5255 0.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1235 -1.3899 -0.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8928 0.5688 -1.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3665 0.7738 -0.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7557 2.5533 -0.3812 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8686 1.4050 0.9793 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2074 3.1263 -0.4448 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2869 2.5519 -1.7565 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6869 1.8205 -1.5962 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8614 -4.2064 0.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3169 -2.4697 1.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1968 -3.2852 -0.5775 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2699 -4.4216 2.4002 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2182 -1.5187 -2.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4080 -0.8422 2.4436 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7952 -0.2455 3.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9929 0.9038 2.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 16 19 1 0 19 20 1 0 20 21 2 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 22 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 33 40 1 0 40 41 1 0 32 42 1 0 8 43 1 0 7 44 1 0 44 45 1 0 11 2 1 0 18 13 1 0 25 20 1 0 38 29 1 0 10 5 1 0 35 30 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 6 53 1 0 9 54 1 0 11 55 1 1 12 56 1 0 12 57 1 0 14 58 1 0 15 59 1 0 17 60 1 0 18 61 1 0 21 62 1 0 23 63 1 0 24 64 1 0 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 29 70 1 6 31 71 1 0 34 72 1 0 36 73 1 0 36 74 1 0 37 75 1 0 37 76 1 0 39 77 1 0 39 78 1 0 39 79 1 0 41 80 1 0 41 81 1 0 41 82 1 0 42 83 1 0 43 84 1 0 45 85 1 0 45 86 1 0 45 87 1 0 M END

Standard InCHIKey	ZKGBUDJODLZAHS-JSOSNVBQSA-N
Standard InCHI	InChI=1S/C37H42N2O6/c1-38-14-12-25-19-35(43-4)32(40)21-28(25)30(38)16-23-6-9-27(10-7-23)45-37-18-24(8-11-34(37)42-3)17-31-29-22-33(41)36(44-5)20-26(29)13-15-39(31)2/h6-11,18-22,30-31,40-41H,12-17H2,1-5H3/t30-,31+/m1/s1
SMILES	CN1CCc2cc(c(cc2[C@H]1Cc1ccc(cc1)Oc1cc(ccc1OC)C[C@H]1c2cc(c(cc2CCN1C)OC)O)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.3	Volume:	640.267 ? Van der Waals volume.
Dense:	0.953	LogP:	3.429 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.926 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.201 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	34.0
TPSA:	83.86 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.224	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.65	Fsp³:	0.351
MCE-18:	113.4 ? 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:	0.986	Fluc inhibitor:	0.198 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.795 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.934 ? 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:	-5.097	MDCK Permeability:	-4.775
Pgp-inhibitor:	0.995	Pgp-substrate:	0.044
PAMPA:	0.0 ? 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):	0.0
20% Bioavailability (F20%):	0.691	30% Bioavailability (F30%):	0.248
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.917	MRP1:	0.993
Plasma Protein Binding (PPB):	66.182%	Volume Distribution (VD):	-0.153
Fu:	37.022% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.953
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:	0.005
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.084
HLM stability:	0.252 ? 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):

4.338

Half-life (T1/2):

2.965

ADMET: Toxicity

hERG Blockers:	0.888	hERG Blockers (10um):	0.761
Human Hepatotoxicity (H-HT):	0.927	Drug-induced Liver Injury (DILI):	0.214
AMES Toxicity:	0.758	Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.988	Skin Sensitization:	0.538
Carcinogencity:	0.389	Eye Corrosion:	0.0
Eye Irritation:	0.034	Respiratory Toxicity:	0.54
Drug-induced Neurotoxicity:	0.926	Ototoxicity:	0.914
Hematotoxicity:	0.063	Drug-induced Nephrotoxicity:	0.297
Genotoxicity:	0.94	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.307	Hek293 Cytotoxicity:	0.93
BCF:	1.828 ? 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:	4.578 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.875 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.253 ? 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
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711348]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919067]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China	2007-JUN	PMID[20550196]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24328302]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18289	Cordia goetzei	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18289	Cordia goetzei	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13124	Eriophorum vaginatum	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17669	Podocarpus borneensis	Species	Podocarpaceae	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 NPC190031 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	26535
0.1-0.2	20549
0.2-0.3	2400
0.3-0.4	193
0.4-0.5	73
0.5-0.6	45
0.6-0.7	43
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC603603
0.8657	High Similarity	NPC286119
0.8154	Intermediate Similarity	NPC480592
0.7581	Intermediate Similarity	NPC247639
0.7581	Intermediate Similarity	NPC25084
0.7536	Intermediate Similarity	NPC240841
0.7361	Intermediate Similarity	NPC311973
0.7324	Intermediate Similarity	NPC290582
0.7324	Intermediate Similarity	NPC217748
0.7324	Intermediate Similarity	NPC182052
0.7324	Intermediate Similarity	NPC271013
0.7324	Intermediate Similarity	NPC42663
0.7324	Intermediate Similarity	NPC15414
0.726	Intermediate Similarity	NPC254441
0.7222	Intermediate Similarity	NPC279228
0.7213	Intermediate Similarity	NPC147390
0.7213	Intermediate Similarity	NPC428
0.7164	Intermediate Similarity	NPC30779
0.7123	Intermediate Similarity	NPC239824
0.6825	Remote Similarity	NPC321505
0.6825	Remote Similarity	NPC179825
0.6806	Remote Similarity	NPC610959
0.68	Remote Similarity	NPC116465
0.6711	Remote Similarity	NPC229373
0.662	Remote Similarity	NPC76682
0.662	Remote Similarity	NPC10908
0.662	Remote Similarity	NPC63646
0.662	Remote Similarity	NPC317145
0.662	Remote Similarity	NPC198498
0.662	Remote Similarity	NPC115284
0.6528	Remote Similarity	NPC276890
0.6522	Remote Similarity	NPC317272
0.6522	Remote Similarity	NPC268503
0.6447	Remote Similarity	NPC600872
0.641	Remote Similarity	NPC181796
0.641	Remote Similarity	NPC290005
0.641	Remote Similarity	NPC54654
0.641	Remote Similarity	NPC7715
0.641	Remote Similarity	NPC328155
0.641	Remote Similarity	NPC222661
0.641	Remote Similarity	NPC285931
0.6351	Remote Similarity	NPC12424
0.6351	Remote Similarity	NPC129518
0.6351	Remote Similarity	NPC251580
0.6308	Remote Similarity	NPC135538
0.6308	Remote Similarity	NPC24233
0.6269	Remote Similarity	NPC104196
0.6267	Remote Similarity	NPC603853
0.625	Remote Similarity	NPC601489
0.625	Remote Similarity	NPC604804
0.6216	Remote Similarity	NPC227060
0.6184	Remote Similarity	NPC73492
0.6184	Remote Similarity	NPC299990
0.6154	Remote Similarity	NPC185639
0.6154	Remote Similarity	NPC251735
0.6154	Remote Similarity	NPC49075
0.6154	Remote Similarity	NPC223690
0.6154	Remote Similarity	NPC9532
0.6154	Remote Similarity	NPC599951
0.6071	Remote Similarity	NPC82457
0.6027	Remote Similarity	NPC256012
0.6027	Remote Similarity	NPC610965
0.5976	Remote Similarity	NPC611658
0.5974	Remote Similarity	NPC480587
0.5909	Remote Similarity	NPC191376
0.5867	Remote Similarity	NPC41376
0.5854	Remote Similarity	NPC212237
0.5823	Remote Similarity	NPC475393
0.5783	Remote Similarity	NPC24260
0.5783	Remote Similarity	NPC8836
0.5698	Remote Similarity	NPC11296
0.5698	Remote Similarity	NPC274661
0.5696	Remote Similarity	NPC608819
0.5679	Remote Similarity	NPC274716
0.5679	Remote Similarity	NPC167116
0.5679	Remote Similarity	NPC609821
0.5625	Remote Similarity	NPC213206
0.5625	Remote Similarity	NPC188163
0.5625	Remote Similarity	NPC328750
0.5618	Remote Similarity	NPC48490
0.5588	Remote Similarity	NPC317439
0.5542	Remote Similarity	NPC195538
0.55	Remote Similarity	NPC609914
0.5476	Remote Similarity	NPC243454
0.5469	Remote Similarity	NPC314682
0.5432	Remote Similarity	NPC600054
0.5432	Remote Similarity	NPC601504
0.5402	Remote Similarity	NPC480586
0.5402	Remote Similarity	NPC480590
0.5373	Remote Similarity	NPC185838
0.5341	Remote Similarity	NPC473589
0.5333	Remote Similarity	NPC41122
0.5333	Remote Similarity	NPC318805
0.5287	Remote Similarity	NPC239584
0.5278	Remote Similarity	NPC295691
0.5278	Remote Similarity	NPC207757
0.5278	Remote Similarity	NPC54379
0.525	Remote Similarity	NPC480591
0.5233	Remote Similarity	NPC485712
0.5233	Remote Similarity	NPC275680
0.5233	Remote Similarity	NPC22115
0.5181	Remote Similarity	NPC601503
0.5132	Remote Similarity	NPC475215
0.5116	Remote Similarity	NPC475479
0.5116	Remote Similarity	NPC323537
0.5072	Remote Similarity	NPC609731
0.5054	Remote Similarity	NPC175890

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190031 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4035
0.1-0.2	4882
0.2-0.3	214
0.3-0.4	12
0.4-0.5	1
0.5-0.6	3
0.6-0.7	3
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
0.662	Remote Similarity	NPD8099	Discontinued
0.6267	Remote Similarity	NPD8156	Discontinued
0.6184	Remote Similarity	NPD8095	Phase 1
0.5714	Remote Similarity	NPD4010	Discontinued
0.5625	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5385	Remote Similarity	NPD8054	Phase 4

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