NPASS Compound

Natural Product: NPC485711

Natural Product ID	NPC485711
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OVPQEGJCNOIBDW-WDYNHAJCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002955] Tetrahydroisoquinolines

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 82 89 0 0 0 0 0 0 0 0999 V2000 -4.3162 4.3588 0.6928 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3903 3.2015 -0.1292 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6319 2.5312 0.0821 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8842 1.7045 -1.1723 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7478 0.7149 -1.1942 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0513 -0.5016 -1.7750 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0968 -1.4725 -1.8479 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8526 -1.2127 -1.3384 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5617 0.0259 -0.7519 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5057 1.0124 -0.6710 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2209 2.3433 -0.0884 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5401 2.3493 1.2257 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0766 2.5513 1.2139 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3928 3.2635 0.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9784 3.3821 0.3402 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6685 2.7767 1.3636 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0212 2.0561 2.3257 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3487 1.9538 2.2348 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0458 2.8990 1.4154 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8454 1.9321 0.7618 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5603 0.6099 0.9137 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2967 -0.3905 0.3068 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3555 0.0241 -0.4773 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6833 1.3517 -0.6615 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9036 2.3073 -0.0228 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2009 3.6451 -0.1820 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3037 4.0431 -0.9955 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9653 -1.8234 0.5180 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9577 -2.3607 -0.4419 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5466 -2.1425 0.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8093 -1.0390 -0.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4732 -0.8982 0.0785 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9891 -1.8857 0.9265 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2357 -2.9782 1.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0350 -3.1129 0.8342 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8696 -4.2899 1.1721 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4318 -4.7935 -0.1419 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1965 -3.7473 -0.7609 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1993 -4.0929 -1.6978 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8844 -3.1922 -2.2552 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2784 -1.7773 1.4161 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7794 -2.7776 2.2706 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2757 0.1800 -0.2673 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1238 -2.3824 -1.5650 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9384 -3.3610 -2.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1771 -2.7526 -2.3820 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7262 4.1882 1.7288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3333 4.8695 0.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0313 5.1220 0.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6387 1.8705 0.9757 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4164 3.3026 0.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7227 2.3692 -2.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8540 1.2014 -1.1693 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0548 -0.7048 -2.1832 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 2.8182 -0.8459 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9412 3.2191 1.8333 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8198 1.4711 1.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9002 3.7543 -0.5189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5315 3.9435 -0.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5814 1.6032 3.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8662 1.3899 2.9847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7268 0.2949 1.5257 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9325 -0.7696 -0.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5342 1.6186 -1.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2603 5.1356 -1.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2094 3.7017 -0.4375 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2827 3.5563 -1.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6108 -1.8830 1.5739 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9286 -2.3709 0.4954 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0917 -1.8010 -1.4090 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2656 -0.3228 -1.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6838 -3.7216 1.9598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2466 -5.0995 1.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7123 -4.0095 1.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5396 -4.9625 -0.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0095 -5.7300 -0.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4082 -5.1117 -1.9610 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7564 -3.7974 1.8053 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8029 -2.5800 2.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0920 -2.8500 3.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4901 -3.7383 -3.1264 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0864 -4.2104 -1.4672 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 39 40 2 0 33 41 1 0 41 42 1 0 32 43 1 0 8 44 1 0 44 45 1 0 45 46 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 46 7 1 0 43 9 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 6 54 1 0 11 55 1 6 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 42 78 1 0 42 79 1 0 42 80 1 0 45 81 1 0 45 82 1 0 M END

Standard InCHIKey	OVPQEGJCNOIBDW-WDYNHAJCSA-N
Standard InCHI	InChI=1S/C37H36N2O7/c1-38-12-10-25-18-34-36(44-21-43-34)37-35(25)29(38)14-22-4-7-26(8-5-22)45-32-16-23(6-9-30(32)41-2)15-28-27-19-33(46-37)31(42-3)17-24(27)11-13-39(28)20-40/h4-9,16-20,28-29H,10-15,21H2,1-3H3/t28-,29+/m1/s1
SMILES	CN1CCc2cc3c(c4c2[C@@H]1Cc1ccc(cc1)Oc1cc(ccc1OC)C[C@@H]1c2cc(c(cc2CCN1C=O)OC)O4)OCO3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.25	Volume:	629.307 ? Van der Waals volume.
Dense:	0.986	LogP:	3.616 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.31 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.143 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	47.0
TPSA:	78.93 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	9.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.244	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.967	Fsp³:	0.324
MCE-18:	141.429 ? 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:	1.0	Fluc inhibitor:	0.258 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.565 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.936 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.025

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.551	MDCK Permeability:	-4.7
Pgp-inhibitor:	0.863	Pgp-substrate:	0.314
PAMPA:	0.025 ? 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%):	0.366	30% Bioavailability (F30%):	0.045
50% Bioavailability (F50%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954	MRP1:	0.818
Plasma Protein Binding (PPB):	94.208%	Volume Distribution (VD):	0.286
Fu:	6.547% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.854
OATP1B3 inhibitor:	0.827	BCRP inhibitor:	0.51
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.261
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.408
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.376
CYP2B6-substrate:	0.771	CYP2C8-inhibitor:	0.935
HLM stability:	0.637 ? 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):

5.679

Half-life (T1/2):

1.587

ADMET: Toxicity

hERG Blockers:	0.402	hERG Blockers (10um):	0.544
Human Hepatotoxicity (H-HT):	0.781	Drug-induced Liver Injury (DILI):	0.717
AMES Toxicity:	0.834	Rat Oral Acute Toxicity:	0.655
Maximum Recommended Daily Dose:	0.976	Skin Sensitization:	0.853
Carcinogencity:	0.874	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.587
Drug-induced Neurotoxicity:	0.935	Ototoxicity:	0.73
Hematotoxicity:	0.429	Drug-induced Nephrotoxicity:	0.73
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.195
A549 Cytotoxicity:	0.418	Hek293 Cytotoxicity:	0.726
BCF:	1.649 ? 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:	4.262 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.021 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.276 ? 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
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129063]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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	1

Activity Type	# Activity
Cell line	1

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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	12000.0	nM	PMID[32129063]

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 NPC485711 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	30385
0.1-0.2	18365
0.2-0.3	899
0.3-0.4	119
0.4-0.5	45
0.5-0.6	31
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8415	Intermediate Similarity	NPC485712
0.7753	Intermediate Similarity	NPC475597
0.7229	Intermediate Similarity	NPC73492
0.7229	Intermediate Similarity	NPC299990
0.6837	Remote Similarity	NPC475654
0.6235	Remote Similarity	NPC76682
0.6235	Remote Similarity	NPC10908
0.6235	Remote Similarity	NPC63646
0.6235	Remote Similarity	NPC317145
0.6235	Remote Similarity	NPC198498
0.6235	Remote Similarity	NPC115284
0.6146	Remote Similarity	NPC281581
0.6064	Remote Similarity	NPC24260
0.5977	Remote Similarity	NPC276890
0.5843	Remote Similarity	NPC12424
0.5843	Remote Similarity	NPC129518
0.5843	Remote Similarity	NPC251580
0.5618	Remote Similarity	NPC41376
0.5604	Remote Similarity	NPC603853
0.5591	Remote Similarity	NPC311973
0.5556	Remote Similarity	NPC227060
0.5556	Remote Similarity	NPC317439
0.5543	Remote Similarity	NPC480587
0.5376	Remote Similarity	NPC290582
0.5376	Remote Similarity	NPC217748
0.5376	Remote Similarity	NPC182052
0.5376	Remote Similarity	NPC271013
0.5376	Remote Similarity	NPC42663
0.5376	Remote Similarity	NPC15414
0.5368	Remote Similarity	NPC116465
0.5319	Remote Similarity	NPC279228
0.5306	Remote Similarity	NPC475479
0.5263	Remote Similarity	NPC239824
0.5208	Remote Similarity	NPC185639
0.5208	Remote Similarity	NPC251735
0.5208	Remote Similarity	NPC254441
0.5208	Remote Similarity	NPC49075
0.5208	Remote Similarity	NPC599951
0.5176	Remote Similarity	NPC247639
0.5176	Remote Similarity	NPC25084
0.5152	Remote Similarity	NPC323537
0.51	Remote Similarity	NPC249996
0.5052	Remote Similarity	NPC223690
0.5052	Remote Similarity	NPC9532

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC485711 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4706
0.1-0.2	4309
0.2-0.3	123
0.3-0.4	9
0.4-0.5	0
0.5-0.6	2
0.6-0.7	1
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
0.6235	Remote Similarity	NPD8099	Discontinued
0.5955	Remote Similarity	NPD8156	Discontinued
0.5543	Remote Similarity	NPD8095	Phase 1

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